Allylation of carbon pronucleophiles with alkynes in the presence of palladium/acetic acid catalyst

Advanced Synthesis and Catalysis

Volumn 346, Issue 7, 2004, Pages 800-804

  Patil, Nitin T ^a   Kadota, Isao ^a   Shibuya, Akinori ^a   Young, Soo Gyoung ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alkynes; Allylation; C C bond formation; Carbon nucleophiles; Homogeneous catalysis; Palladium

Indexed keywords

ACETIC ACID; ALKYNE DERIVATIVE; CARBENE; CARBON; CARBOXYLIC ACID; PALLADIUM;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; STOICHIOMETRY;

EID: 4143123249     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404046     Document Type: Article

References (40)

1. For recent reviews, see: a) S. Godleski, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Vol. 4, Pergamon Press, New York, 1991, pp. 585-661; b) J. A. Davies, in: Comprehensive Organometallic Chemistry II, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Vol. 9, Pergamon Press, Oxford, 1995, pp. 291-390; c) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1995, pp. 290-340; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; e) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; f) B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395-422; g) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364; for recent references, see: h) C. Commandeur, S. Thorimbert, M. Malacria, J. Org. Chem. 2003, 68, 5588-5592; i) M. Kawamura, R. Kiyotake, K. Kudo, Chirality, 2002, 14, 724-726; for ruthenium-catalyzed allylic alkylations, see: j) B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. Int. Ed. 2002, 41, 1059-1061; for iridium-catalyzed allylic substitutions with phenoxide, see: k) F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427 and referenced cited therein.
2. For recent reviews, see: a) S. Godleski, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Vol. 4, Pergamon Press, New York, 1991, pp. 585-661; b) J. A. Davies, in: Comprehensive Organometallic Chemistry II, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Vol. 9, Pergamon Press, Oxford, 1995, pp. 291-390; c) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1995, pp. 290-340; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; e) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; f) B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395-422; g) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364; for recent references, see: h) C. Commandeur, S. Thorimbert, M. Malacria, J. Org. Chem. 2003, 68, 5588-5592; i) M. Kawamura, R. Kiyotake, K. Kudo, Chirality, 2002, 14, 724-726; for ruthenium-catalyzed allylic alkylations, see: j) B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. Int. Ed. 2002, 41, 1059-1061; for iridium-catalyzed allylic substitutions with phenoxide, see: k) F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427 and referenced cited therein.
3. For recent reviews, see: a) S. Godleski, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Vol. 4, Pergamon Press, New York, 1991, pp. 585-661; b) J. A. Davies, in: Comprehensive Organometallic Chemistry II, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Vol. 9, Pergamon Press, Oxford, 1995, pp. 291-390; c) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1995, pp. 290-340; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; e) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; f) B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395-422; g) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364; for recent references, see: h) C. Commandeur, S. Thorimbert, M. Malacria, J. Org. Chem. 2003, 68, 5588-5592; i) M. Kawamura, R. Kiyotake, K. Kudo, Chirality, 2002, 14, 724-726; for ruthenium-catalyzed allylic alkylations, see: j) B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. Int. Ed. 2002, 41, 1059-1061; for iridium-catalyzed allylic substitutions with phenoxide, see: k) F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427 and referenced cited therein.
4. For recent reviews, see: a) S. Godleski, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Vol. 4, Pergamon Press, New York, 1991, pp. 585-661; b) J. A. Davies, in: Comprehensive Organometallic Chemistry II, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Vol. 9, Pergamon Press, Oxford, 1995, pp. 291-390; c) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1995, pp. 290-340; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; e) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; f) B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395-422; g) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364; for recent references, see: h) C. Commandeur, S. Thorimbert, M. Malacria, J. Org. Chem. 2003, 68, 5588-5592; i) M. Kawamura, R. Kiyotake, K. Kudo, Chirality, 2002, 14, 724-726; for ruthenium-catalyzed allylic alkylations, see: j) B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. Int. Ed. 2002, 41, 1059-1061; for iridium-catalyzed allylic substitutions with phenoxide, see: k) F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427 and referenced cited therein.
5. For recent reviews, see: a) S. Godleski, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Vol. 4, Pergamon Press, New York, 1991, pp. 585-661; b) J. A. Davies, in: Comprehensive Organometallic Chemistry II, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Vol. 9, Pergamon Press, Oxford, 1995, pp. 291-390; c) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1995, pp. 290-340; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; e) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; f) B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395-422; g) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364; for recent references, see: h) C. Commandeur, S. Thorimbert, M. Malacria, J. Org. Chem. 2003, 68, 5588-5592; i) M. Kawamura, R. Kiyotake, K. Kudo, Chirality, 2002, 14, 724-726; for ruthenium-catalyzed allylic alkylations, see: j) B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. Int. Ed. 2002, 41, 1059-1061; for iridium-catalyzed allylic substitutions with phenoxide, see: k) F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427 and referenced cited therein.
6. For recent reviews, see: a) S. Godleski, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Vol. 4, Pergamon Press, New York, 1991, pp. 585-661; b) J. A. Davies, in: Comprehensive Organometallic Chemistry II, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Vol. 9, Pergamon Press, Oxford, 1995, pp. 291-390; c) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1995, pp. 290-340; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; e) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; f) B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395-422; g) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364; for recent references, see: h) C. Commandeur, S. Thorimbert, M. Malacria, J. Org. Chem. 2003, 68, 5588-5592; i) M. Kawamura, R. Kiyotake, K. Kudo, Chirality, 2002, 14, 724-726; for ruthenium-catalyzed allylic alkylations, see: j) B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. Int. Ed. 2002, 41, 1059-1061; for iridium-catalyzed allylic substitutions with phenoxide, see: k) F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427 and referenced cited therein.
7. For recent reviews, see: a) S. Godleski, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Vol. 4, Pergamon Press, New York, 1991, pp. 585-661; b) J. A. Davies, in: Comprehensive Organometallic Chemistry II, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Vol. 9, Pergamon Press, Oxford, 1995, pp. 291-390; c) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1995, pp. 290-340; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; e) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; f) B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395-422; g) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364; for recent references, see: h) C. Commandeur, S. Thorimbert, M. Malacria, J. Org. Chem. 2003, 68, 5588-5592; i) M. Kawamura, R. Kiyotake, K. Kudo, Chirality, 2002, 14, 724-726; for ruthenium-catalyzed allylic alkylations, see: j) B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. Int. Ed. 2002, 41, 1059-1061; for iridium-catalyzed allylic substitutions with phenoxide, see: k) F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427 and referenced cited therein.
8. For recent reviews, see: a) S. Godleski, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Vol. 4, Pergamon Press, New York, 1991, pp. 585-661; b) J. A. Davies, in: Comprehensive Organometallic Chemistry II, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Vol. 9, Pergamon Press, Oxford, 1995, pp. 291-390; c) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1995, pp. 290-340; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; e) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; f) B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395-422; g) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364; for recent references, see: h) C. Commandeur, S. Thorimbert, M. Malacria, J. Org. Chem. 2003, 68, 5588-5592; i) M. Kawamura, R. Kiyotake, K. Kudo, Chirality, 2002, 14, 724-726; for ruthenium-catalyzed allylic alkylations, see: j) B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. Int. Ed. 2002, 41, 1059-1061; for iridium-catalyzed allylic substitutions with phenoxide, see: k) F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427 and referenced cited therein.
9. For recent reviews, see: a) S. Godleski, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Vol. 4, Pergamon Press, New York, 1991, pp. 585-661; b) J. A. Davies, in: Comprehensive Organometallic Chemistry II, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Vol. 9, Pergamon Press, Oxford, 1995, pp. 291-390; c) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1995, pp. 290-340; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; e) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; f) B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395-422; g) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364; for recent references, see: h) C. Commandeur, S. Thorimbert, M. Malacria, J. Org. Chem. 2003, 68, 5588-5592; i) M. Kawamura, R. Kiyotake, K. Kudo, Chirality, 2002, 14, 724-726; for ruthenium-catalyzed allylic alkylations, see: j) B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. Int. Ed. 2002, 41, 1059-1061; for iridium-catalyzed allylic substitutions with phenoxide, see: k) F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427 and referenced cited therein.
10. For recent reviews, see: a) S. Godleski, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Vol. 4, Pergamon Press, New York, 1991, pp. 585-661; b) J. A. Davies, in: Comprehensive Organometallic Chemistry II, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Vol. 9, Pergamon Press, Oxford, 1995, pp. 291-390; c) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1995, pp. 290-340; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; e) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; f) B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395-422; g) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364; for recent references, see: h) C. Commandeur, S. Thorimbert, M. Malacria, J. Org. Chem. 2003, 68, 5588-5592; i) M. Kawamura, R. Kiyotake, K. Kudo, Chirality, 2002, 14, 724-726; for ruthenium-catalyzed allylic alkylations, see: j) B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. Int. Ed. 2002, 41, 1059-1061; for iridium-catalyzed allylic substitutions with phenoxide, see: k) F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427 and referenced cited therein.
11. For recent reviews, see: a) S. Godleski, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Vol. 4, Pergamon Press, New York, 1991, pp. 585-661; b) J. A. Davies, in: Comprehensive Organometallic Chemistry II, (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Vol. 9, Pergamon Press, Oxford, 1995, pp. 291-390; c) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, Wiley, Chichester, 1995, pp. 290-340; d) G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257-276; e) C. G. Frost, J. Howarth, J. M. J. Williams, Tetrahedron: Asymmetry 1992, 3, 1089-1122; f) B. M. Trost, D. L. V. Vranken, Chem. Rev. 1996, 96, 395-422; g) B. M. Trost, Acc. Chem. Res. 1996, 29, 355-364; for recent references, see: h) C. Commandeur, S. Thorimbert, M. Malacria, J. Org. Chem. 2003, 68, 5588-5592; i) M. Kawamura, R. Kiyotake, K. Kudo, Chirality, 2002, 14, 724-726; for ruthenium-catalyzed allylic alkylations, see: j) B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. Int. Ed. 2002, 41, 1059-1061; for iridium-catalyzed allylic substitutions with phenoxide, see: k) F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427 and referenced cited therein.
12. J. Tsuji, Transition Metal Reagents and Catalysts, Wiley, New York, 2000, Chapter 4.
13. 2: M. Sakamoto, I. Shimizu, A. Yamamoto, Bull. Chem. Soc. Jpn. 1996, 69, 1065; d) F. Ozawa, H. Okamoto, S. Kawagishi, S. Yamamoto, T. Minami, M. Yoshifuji, J. Am. Chem. Soc. 2002, 124, 10968-10969 and references cited therein.
14. 2: M. Sakamoto, I. Shimizu, A. Yamamoto, Bull. Chem. Soc. Jpn. 1996, 69, 1065; d) F. Ozawa, H. Okamoto, S. Kawagishi, S. Yamamoto, T. Minami, M. Yoshifuji, J. Am. Chem. Soc. 2002, 124, 10968-10969 and references cited therein.
15. 2: M. Sakamoto, I. Shimizu, A. Yamamoto, Bull. Chem. Soc. Jpn. 1996, 69, 1065; d) F. Ozawa, H. Okamoto, S. Kawagishi, S. Yamamoto, T. Minami, M. Yoshifuji, J. Am. Chem. Soc. 2002, 124, 10968-10969 and references cited therein.
16. 2: M. Sakamoto, I. Shimizu, A. Yamamoto, Bull. Chem. Soc. Jpn. 1996, 69, 1065; d) F. Ozawa, H. Okamoto, S. Kawagishi, S. Yamamoto, T. Minami, M. Yoshifuji, J. Am. Chem. Soc. 2002, 124, 10968-10969 and references cited therein.
17. Although allylic carbonates and epoxides react with pronucleophiles in the absence of an external base, a stoichiometric amount of alkoxides generated from the substrates acts as a base in these reactions.
18. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
19. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
20. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
21. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
22. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
23. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
24. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
25. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
26. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
27. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
28. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
29. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
30. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
31. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
32. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
33. For preliminary communication, see: a) I. Kadota, A. Shibuya, Y. S. Gyoung, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 10262-10263; during the course of these studies, we also reported the hydroamination and hydroalkoxylaton of alkynes, see: b) I. Kadota, A. Shibuya, M. L. Lutete, Y. Yamamoto, J. Org. Chem. 1999, 64, 4570-4571; c) M. L. Lutete, I. Kadota, A. Shibuya, Y. Yamamoto, Heterocycles. 2002, 58, 347-357; d) I. Kadota, M. L. Lutete, A. Shibuya, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6207-6210. While the work was in progress, another group reported the hydrocarboxylation of alkynes based on the same concept, see: e) W. Zhang, A. R Haight, M. C. Hsu, Tetrahedron Lett. 2002, 43, 6575-6578. We also reported, previously, the hydrocarbonaton of the substrates other than alkynes. For hydrocarbonation of allenes, see: f) Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020; g) Y. Yamamoto, M. Al-Masum, N. Fujiwara, Chem. Commun. 1996, 381-382; h) Y. Yamamoto, M. Al-Masum, A. Takeda, Chem. Commun. 1996, 831-832; i) Y. Yamamoto, M. Al-Masum, N. Fujiwara, N. Asao, Tetrahedron Lett. 1995, 36, 2811-2814; j) Y. Yamamoto, M. Al-Masum, Synlett 1995, 969-970; k) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453-7456. For the hydrocarbonation of 1,3-enynes, see: l) M. M. Salter, V. Gevorgyan, S. Saito, Y. Yamamoto, Chem. Commun. 1996, 17; for the hydrocarbonation of 3,3-dihexylcyclopropene, see: m) I. Nakamura, G. B. Bajracharya, Y. Yamamoto, J. Org. Chem. 2003, 68, 2297-2299. For the hydrocarbonation of methyleneaziridines, see: n) B. H. Oh, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2002, 43, 9625-9628. For the hydrocarbonation of methylenecyclopropanes, see: o) N. Tsukada, A. Shibuya, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 8123; p) N. Tsukada, A. Shibuya, I. Nakamura, H. Kitahara, Y. Yamamoto, Tetrahedron 1999, 55, 8833.
34. 2Ph. Therefore, we chose malononitrile as a model substrate for active methylenes.
35. Enhancement of reaction rate by the use of Pd(0)/carboxylic acid combined catalytic system is also observed by others, see: a) B. M. Trost, F. Rise, J. Am. Chem. Soc. 1987, 109, 3161-3163; b) B. M. Trost, C. Jakel, B. Plietker, J. Am. Chem. Soc. 2003, 125, 4438-4439.
36. Enhancement of reaction rate by the use of Pd(0)/carboxylic acid combined catalytic system is also observed by others, see: a) B. M. Trost, F. Rise, J. Am. Chem. Soc. 1987, 109, 3161-3163; b) B. M. Trost, C. Jakel, B. Plietker, J. Am. Chem. Soc. 2003, 125, 4438-4439.
37. [5a] but later found that 10 mol % of acetic acid was also enough without affecting the reaction in terms of yield, time and regioselectivity.
38. Palladium-catalyzed isomerization of alkynes to allenes, see: a) H. Sheng, S. Lin, Y. Huang, Tetrahedron Lett. 1986, 27, 4893-4894; b) B. M. Trost, T. Schmidt, J. Am. Chem. Soc. 1988, 110, 2301-2303; c) X. Lu, J. Ji, D. Ma, W. Shen, J. Org. Chem. 1991, 56, 5774-5778.
39. Palladium-catalyzed isomerization of alkynes to allenes, see: a) H. Sheng, S. Lin, Y. Huang, Tetrahedron Lett. 1986, 27, 4893-4894; b) B. M. Trost, T. Schmidt, J. Am. Chem. Soc. 1988, 110, 2301-2303; c) X. Lu, J. Ji, D. Ma, W. Shen, J. Org. Chem. 1991, 56, 5774-5778.
40. Palladium-catalyzed isomerization of alkynes to allenes, see: a) H. Sheng, S. Lin, Y. Huang, Tetrahedron Lett. 1986, 27, 4893-4894; b) B. M. Trost, T. Schmidt, J. Am. Chem. Soc. 1988, 110, 2301-2303; c) X. Lu, J. Ji, D. Ma, W. Shen, J. Org. Chem. 1991, 56, 5774-5778.