Palladium-catalyzed Heck and carbonylation reactions of a dinaphthaleneiodonium salt forming functionalized 2-iodo-1,1′-binaphthyls

Advanced Synthesis and Catalysis

Volumn 346, Issue 13-15, 2004, Pages 1728-1732

  Kina, Asato ^a   Miki, Hiroyuki ^a   Cho, Yong Hwan ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Binaphthyl; Carbonylation; Heck reaction; Iodonium salt; Palladium catalyst

Indexed keywords

BINAPHTHALENEIODONIUM; NAPHTHALENE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; HECK REACTION; OLEFINATION;

EID: 12344264763     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404202     Document Type: Article

References (22)

1. For reviews, see: a) R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345; b) C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503; c) L. Pu, Chem. Rev. 1998, 98, 2405; d) M. McCarthy, P. J. Guiry, Tetrahedron 2001, 57, 3809.
2. For reviews, see: a) R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345; b) C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503; c) L. Pu, Chem. Rev. 1998, 98, 2405; d) M. McCarthy, P. J. Guiry, Tetrahedron 2001, 57, 3809.
3. For reviews, see: a) R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345; b) C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503; c) L. Pu, Chem. Rev. 1998, 98, 2405; d) M. McCarthy, P. J. Guiry, Tetrahedron 2001, 57, 3809.
4. For reviews, see: a) R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345; b) C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503; c) L. Pu, Chem. Rev. 1998, 98, 2405; d) M. McCarthy, P. J. Guiry, Tetrahedron 2001, 57, 3809.
5. For reviews, see: a) T. Hayashi, Acc. Chem. Res. 2000, 33, 354; b) P. Kocovsky, S. Vyskocil, M. Smrcina, Chem. Rev. 2003, 103, 3213.
6. For reviews, see: a) T. Hayashi, Acc. Chem. Res. 2000, 33, 354; b) P. Kocovsky, S. Vyskocil, M. Smrcina, Chem. Rev. 2003, 103, 3213.
7. a) T. Shimada, Y.-H. Cho, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 13396;
8. b) Y.-H. Cho, A. Kina, T. Shimada, T. Hayashi, J. Org. Chem. 2004, 69, 3811.
9. For reviews on the iodonium salts, see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123; b) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523.
10. For reviews on the iodonium salts, see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123; b) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523.
11. Q. Zhu, J. Wu, R. Fathi, Z. Yang, Org. Lett. 2002, 4, 3333.
12. For a review on the Heck reaction, see: I. P. Beletsukaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
13. S.-K. Kan, T. Yamaguchi, P.-S. Ho, W.-Y. Kim, H.-C. Ryu, J. Chem. Soc. Perkin Trans. 1998, 841.
14. - has been reported briefly to be formed as an undesired product: M. Ochiai, Y. Kitagawa, N. Takayama, Y. Takaoka, M. Shiro, J. Am. Chem. Soc. 1999, 121, 9233.
15. M. Ochiai, Y. Takaoka, Y. Masaki, J. Am. Chem. Soc. 1990, 112, 5677, and references cited therein.
16. D. Fabbri, G. Delogue, O. De Lucchi, J. Org. Chem. 1993, 58, 1748.
17. A. McKillop, D. Kemp, Tetrahedron 1989, 45, 3299.
18. a) J. Collette, D. McGreer, R. Crawford, F. Chubb, R. B. Sandin, J. Am. Chem. Soc. 1956, 78, 3819;
19. b) T. Kitamura, J. Matsuyuki, K. Nagata, R. Furuki, H. Taniguchi, Synthesis 1992, 945.
20. A cyclic diphenyleneiodonium salt has been reported to give a low yield of a Heck-type product: Y. Liang, S. Luo, C. Liu, X. Wu, Y. Ma, Tetrahedron 2000, 56, 2961.
21. An analogous cyclic product has been reported in the Heck reaction of 2,2′-dibromobiphenyl: M. Prashad, Y. Liu, X. Y. Mak, D. Har, O. Repic, T. J. Blacklock, Tetrahedron Lett. 2002, 43, 8559.
22. M. Brookhart, B. Grant, A. F. Volpe Jr., Organometallics 1992, 11, 3920.