Palladium(0)-catalyzed intramolecular [2+2+2] alkyne cyclotrimerizations with electron-deficient diynes and triynes

Chemistry - A European Journal

Volumn 9, Issue 11, 2003, Pages 2469-2483

  Yamamoto, Yoshihiko ^a   Nagata, Asako ^a   Nagata, Hitomi ^a   Ando, Yoji ^a   Arikawa, Yasuhiro ^a   Tatsumi, Kazuyuki ^a   Itoh, Kenji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Alkynes; Cyclotrimerization; Homogeneous catalysis; Metallacycles; Palladium

Indexed keywords

CATALYSIS; ELECTRONS; ESTERS; PALLADIUM COMPOUNDS; STOICHIOMETRY; TOLUENE;

CYCLOTRIMERIZATION;

ORGANOMETALLICS;

ACETONE; ALKYNE DERIVATIVE; BICYCLOPALLADACYCLOPENTADIENE; DIACETYLENE DICARBOXYLATE; DIBENZYLIDENEACETONE; DIMETHYLNONA 2,7 DIYNE 1,9 DIOATE; DIMETHYLTRIDECA 2,7,12 TRIYNE 1,13 DIOATE; OLIGOMER; PALLADIUM; PHTHALIC ACID DERIVATIVE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); CYCLIZATION; CYCLOADDITION; REACTION ANALYSIS; ROOM TEMPERATURE; STOICHIOMETRY; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE; X RAY ANALYSIS;

EID: 0037592751     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200204540     Document Type: Article

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86. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
87. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
88. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
89. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
90. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
91. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
92. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
93. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
94. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
95. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
96. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
97. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
98. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
99. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
100. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
101. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
102. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
103. For catalytic intramolecular alkyne [2+2+2] cycloadditions, see: a) K. P. C. Vollhardt, R. G. Bergman, J. Am. Chem. Soc. 1974, 96, 4996-4998; b) R. L. Hillard, III, K. P. C. Vollhardt, Angew. Chem. 1975, 87, 744-745; Angew. Chem. Int. Ed. Engl. 1975, 14, 712-713; c) R. L. Hillard, III, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 4058-4069; d) R. Grigg, R. Scott, P. Stevenson, Tetrahedron Lett. 1982, 23, 2691-2692; e) R. Grigg, R. Scott, P. Stevenson, J. Chem. Soc. Perkin Trans. 1 1998, 1357-1364; f) G. P. Chiusoli, L. Pallini, G. Terenghi, Transition Met. Chem. 1983, 8, 189-190; g) A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse, Organometallics 1989, 8, 1566-1567; h) C. J. Du Toit, J. A. K. Du Plessis, G. Lachmann, J. Mol. Catal. 1989, 53, 67-78; i) Y. Badrieh, J. Blum, I. Amer, K. P. C. Vollhardt, J. Mol. Catal. 1991, 66, 295-312; j) Y. Sato, T. Nishimata, M. Mori, J. Org. Chem. 1994, 59, 6133-6135; k) Y. Sato, T. Nishimata, M. Mori, Heterocycles 1997, 44, 443-457; l) M. Nishida, H. Shiga, M. Mori, J. Org. Chem. 1998, 63, 8606-8608; m) Y. Yamamoto, R. Ogawa, K. Itoh, Chem. Commun. 2000, 549-550; n) O. V. Ozerov, B. O. Patrick, F. T. Ladipo, J. Am. Chem. Soc. 2000, 122, 6423-6431; o) R. Takeuchi, S. Tanaka, Y. Nakata, Tetrahedron Lett. 2001, 42, 2991-2994; p) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth. Catal. 2001, 343, 64-67; q) A. Jeevanandam, R. P. Korivi, I. Huang, C.-H. Cheng, Org. Lett. 2002, 4, 807-810; r) B. Witulski, A. Zimmermann, Synlett 2002, 1855-1859.
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