Pd11-catalyzed cyclization of alkynes containing aldehyde, ketone, or nitrile groups initiated by the acetoxypalladation of alkynes

Angewandte Chemie - International Edition

Volumn 41, Issue 22, 2002, Pages 4343-4345

  Zhao, Ligang ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Carbonyl ligands; Insertion; N ligands; Nitrile group; Palladium

Indexed keywords

ALDEHYDES; CATALYSIS; ORGANOMETALLICS; REDOX REACTIONS;

REAGENTS;

HYDROCARBONS;

ALDEHYDE DERIVATIVE; ALKYNE DERIVATIVE; KETONE DERIVATIVE; NITRILE; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION;

EID: 0037112644     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021115)41:22<4343::AID-ANIE4343>3.0.CO;2-5     Document Type: Article

References (41)

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9. For recent rhodium-catalyzed reactions using stoichiometric organo-metallic reagents, see: a) T. Huang, Y. Meng, S. Venkatraman, D. Wang, C. J. Li, J. Am. Chem. Soc. 2001, 123, 7451; b) C. J. Li, Y. Meng, J. Am. Chem. Soc. 2000, 122, 9538; c) S. Oi, M. Moro, Y. Inoue, Organometallics 2001, 20, 1036; d) M. Sakai, M. Ueda, N. Miyaura, Angew. Chem. 1998, 110, 3475; Angew. Chem. Int. Ed. 1998, 37, 3279; e) T. Fujii, T. Koike, A. Mori, K. Osakada, Synlett 2002, 298; f) T. Hayashi, M. Ishigedani, J. Am. Chem. Soc. 2000, 122, 976; g) R. A. Batey, A. N. Thadani, D. V. Smil, Org. Lett. 1999, 1, 1683; h) T. Ishiyama, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 12043; i) C. Krug, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 1674.
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11. For recent rhodium-catalyzed reactions using stoichiometric organo-metallic reagents, see: a) T. Huang, Y. Meng, S. Venkatraman, D. Wang, C. J. Li, J. Am. Chem. Soc. 2001, 123, 7451; b) C. J. Li, Y. Meng, J. Am. Chem. Soc. 2000, 122, 9538; c) S. Oi, M. Moro, Y. Inoue, Organometallics 2001, 20, 1036; d) M. Sakai, M. Ueda, N. Miyaura, Angew. Chem. 1998, 110, 3475; Angew. Chem. Int. Ed. 1998, 37, 3279; e) T. Fujii, T. Koike, A. Mori, K. Osakada, Synlett 2002, 298; f) T. Hayashi, M. Ishigedani, J. Am. Chem. Soc. 2000, 122, 976; g) R. A. Batey, A. N. Thadani, D. V. Smil, Org. Lett. 1999, 1, 1683; h) T. Ishiyama, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 12043; i) C. Krug, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 1674.
12. For recent rhodium-catalyzed reactions using stoichiometric organo-metallic reagents, see: a) T. Huang, Y. Meng, S. Venkatraman, D. Wang, C. J. Li, J. Am. Chem. Soc. 2001, 123, 7451; b) C. J. Li, Y. Meng, J. Am. Chem. Soc. 2000, 122, 9538; c) S. Oi, M. Moro, Y. Inoue, Organometallics 2001, 20, 1036; d) M. Sakai, M. Ueda, N. Miyaura, Angew. Chem. 1998, 110, 3475; Angew. Chem. Int. Ed. 1998, 37, 3279; e) T. Fujii, T. Koike, A. Mori, K. Osakada, Synlett 2002, 298; f) T. Hayashi, M. Ishigedani, J. Am. Chem. Soc. 2000, 122, 976; g) R. A. Batey, A. N. Thadani, D. V. Smil, Org. Lett. 1999, 1, 1683; h) T. Ishiyama, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 12043; i) C. Krug, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 1674.
13. For recent rhodium-catalyzed reactions using stoichiometric organo-metallic reagents, see: a) T. Huang, Y. Meng, S. Venkatraman, D. Wang, C. J. Li, J. Am. Chem. Soc. 2001, 123, 7451; b) C. J. Li, Y. Meng, J. Am. Chem. Soc. 2000, 122, 9538; c) S. Oi, M. Moro, Y. Inoue, Organometallics 2001, 20, 1036; d) M. Sakai, M. Ueda, N. Miyaura, Angew. Chem. 1998, 110, 3475; Angew. Chem. Int. Ed. 1998, 37, 3279; e) T. Fujii, T. Koike, A. Mori, K. Osakada, Synlett 2002, 298; f) T. Hayashi, M. Ishigedani, J. Am. Chem. Soc. 2000, 122, 976; g) R. A. Batey, A. N. Thadani, D. V. Smil, Org. Lett. 1999, 1, 1683; h) T. Ishiyama, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 12043; i) C. Krug, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 1674.
14. For recent rhodium-catalyzed reactions using stoichiometric organo-metallic reagents, see: a) T. Huang, Y. Meng, S. Venkatraman, D. Wang, C. J. Li, J. Am. Chem. Soc. 2001, 123, 7451; b) C. J. Li, Y. Meng, J. Am. Chem. Soc. 2000, 122, 9538; c) S. Oi, M. Moro, Y. Inoue, Organometallics 2001, 20, 1036; d) M. Sakai, M. Ueda, N. Miyaura, Angew. Chem. 1998, 110, 3475; Angew. Chem. Int. Ed. 1998, 37, 3279; e) T. Fujii, T. Koike, A. Mori, K. Osakada, Synlett 2002, 298; f) T. Hayashi, M. Ishigedani, J. Am. Chem. Soc. 2000, 122, 976; g) R. A. Batey, A. N. Thadani, D. V. Smil, Org. Lett. 1999, 1, 1683; h) T. Ishiyama, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 12043; i) C. Krug, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 1674.
15. For recent rhodium-catalyzed reactions using stoichiometric organo-metallic reagents, see: a) T. Huang, Y. Meng, S. Venkatraman, D. Wang, C. J. Li, J. Am. Chem. Soc. 2001, 123, 7451; b) C. J. Li, Y. Meng, J. Am. Chem. Soc. 2000, 122, 9538; c) S. Oi, M. Moro, Y. Inoue, Organometallics 2001, 20, 1036; d) M. Sakai, M. Ueda, N. Miyaura, Angew. Chem. 1998, 110, 3475; Angew. Chem. Int. Ed. 1998, 37, 3279; e) T. Fujii, T. Koike, A. Mori, K. Osakada, Synlett 2002, 298; f) T. Hayashi, M. Ishigedani, J. Am. Chem. Soc. 2000, 122, 976; g) R. A. Batey, A. N. Thadani, D. V. Smil, Org. Lett. 1999, 1, 1683; h) T. Ishiyama, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 12043; i) C. Krug, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 1674.
16. For nickel-catalyzed reactions, see: a) Y. Sato, N. Saito, M. Mori, J. Am. Chem. Soc. 2000, 122, 2371; b) Y. Sato, M. Takimoto, K. Hayashi, T. Katsuhara, K. Takagi, M. Mori. J. Am. Chem. Soc. 1994, 116, 9771; c) K. Shibata, M. Kimura, M. Shimizu, Y. Tamaru, Org. Lett. 2001, 3, 2181; d) K. K. Majumdar, C.-H. Cheng, Org. Lett. 2000, 2, 2295; e) Y.C. Huang, K. K. Majumdar, C.-H. Cheng, J. Org. Chem. 2002, 67, 1682; f) E. Oblinger, J. Montgomery, J. Am. Chem. Soc. 1997, 119, 9065; g) M. V. Chevliakov, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 11139; h) K. K. D. Amarasinghe, J. Montgomery, J. Am. Chem. Soc. 2002, 124, 9366.
17. For nickel-catalyzed reactions, see: a) Y. Sato, N. Saito, M. Mori, J. Am. Chem. Soc. 2000, 122, 2371; b) Y. Sato, M. Takimoto, K. Hayashi, T. Katsuhara, K. Takagi, M. Mori. J. Am. Chem. Soc. 1994, 116, 9771; c) K. Shibata, M. Kimura, M. Shimizu, Y. Tamaru, Org. Lett. 2001, 3, 2181; d) K. K. Majumdar, C.-H. Cheng, Org. Lett. 2000, 2, 2295; e) Y.C. Huang, K. K. Majumdar, C.-H. Cheng, J. Org. Chem. 2002, 67, 1682; f) E. Oblinger, J. Montgomery, J. Am. Chem. Soc. 1997, 119, 9065; g) M. V. Chevliakov, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 11139; h) K. K. D. Amarasinghe, J. Montgomery, J. Am. Chem. Soc. 2002, 124, 9366.
18. For nickel-catalyzed reactions, see: a) Y. Sato, N. Saito, M. Mori, J. Am. Chem. Soc. 2000, 122, 2371; b) Y. Sato, M. Takimoto, K. Hayashi, T. Katsuhara, K. Takagi, M. Mori. J. Am. Chem. Soc. 1994, 116, 9771; c) K. Shibata, M. Kimura, M. Shimizu, Y. Tamaru, Org. Lett. 2001, 3, 2181; d) K. K. Majumdar, C.-H. Cheng, Org. Lett. 2000, 2, 2295; e) Y.C. Huang, K. K. Majumdar, C.-H. Cheng, J. Org. Chem. 2002, 67, 1682; f) E. Oblinger, J. Montgomery, J. Am. Chem. Soc. 1997, 119, 9065; g) M. V. Chevliakov, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 11139; h) K. K. D. Amarasinghe, J. Montgomery, J. Am. Chem. Soc. 2002, 124, 9366.
19. For nickel-catalyzed reactions, see: a) Y. Sato, N. Saito, M. Mori, J. Am. Chem. Soc. 2000, 122, 2371; b) Y. Sato, M. Takimoto, K. Hayashi, T. Katsuhara, K. Takagi, M. Mori. J. Am. Chem. Soc. 1994, 116, 9771; c) K. Shibata, M. Kimura, M. Shimizu, Y. Tamaru, Org. Lett. 2001, 3, 2181; d) K. K. Majumdar, C.-H. Cheng, Org. Lett. 2000, 2, 2295; e) Y.C. Huang, K. K. Majumdar, C.-H. Cheng, J. Org. Chem. 2002, 67, 1682; f) E. Oblinger, J. Montgomery, J. Am. Chem. Soc. 1997, 119, 9065; g) M. V. Chevliakov, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 11139; h) K. K. D. Amarasinghe, J. Montgomery, J. Am. Chem. Soc. 2002, 124, 9366.
20. For nickel-catalyzed reactions, see: a) Y. Sato, N. Saito, M. Mori, J. Am. Chem. Soc. 2000, 122, 2371; b) Y. Sato, M. Takimoto, K. Hayashi, T. Katsuhara, K. Takagi, M. Mori. J. Am. Chem. Soc. 1994, 116, 9771; c) K. Shibata, M. Kimura, M. Shimizu, Y. Tamaru, Org. Lett. 2001, 3, 2181; d) K. K. Majumdar, C.-H. Cheng, Org. Lett. 2000, 2, 2295; e) Y.C. Huang, K. K. Majumdar, C.-H. Cheng, J. Org. Chem. 2002, 67, 1682; f) E. Oblinger, J. Montgomery, J. Am. Chem. Soc. 1997, 119, 9065; g) M. V. Chevliakov, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 11139; h) K. K. D. Amarasinghe, J. Montgomery, J. Am. Chem. Soc. 2002, 124, 9366.
21. For nickel-catalyzed reactions, see: a) Y. Sato, N. Saito, M. Mori, J. Am. Chem. Soc. 2000, 122, 2371; b) Y. Sato, M. Takimoto, K. Hayashi, T. Katsuhara, K. Takagi, M. Mori. J. Am. Chem. Soc. 1994, 116, 9771; c) K. Shibata, M. Kimura, M. Shimizu, Y. Tamaru, Org. Lett. 2001, 3, 2181; d) K. K. Majumdar, C.-H. Cheng, Org. Lett. 2000, 2, 2295; e) Y.C. Huang, K. K. Majumdar, C.-H. Cheng, J. Org. Chem. 2002, 67, 1682; f) E. Oblinger, J. Montgomery, J. Am. Chem. Soc. 1997, 119, 9065; g) M. V. Chevliakov, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 11139; h) K. K. D. Amarasinghe, J. Montgomery, J. Am. Chem. Soc. 2002, 124, 9366.
22. For nickel-catalyzed reactions, see: a) Y. Sato, N. Saito, M. Mori, J. Am. Chem. Soc. 2000, 122, 2371; b) Y. Sato, M. Takimoto, K. Hayashi, T. Katsuhara, K. Takagi, M. Mori. J. Am. Chem. Soc. 1994, 116, 9771; c) K. Shibata, M. Kimura, M. Shimizu, Y. Tamaru, Org. Lett. 2001, 3, 2181; d) K. K. Majumdar, C.-H. Cheng, Org. Lett. 2000, 2, 2295; e) Y.C. Huang, K. K. Majumdar, C.-H. Cheng, J. Org. Chem. 2002, 67, 1682; f) E. Oblinger, J. Montgomery, J. Am. Chem. Soc. 1997, 119, 9065; g) M. V. Chevliakov, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 11139; h) K. K. D. Amarasinghe, J. Montgomery, J. Am. Chem. Soc. 2002, 124, 9366.
23. For nickel-catalyzed reactions, see: a) Y. Sato, N. Saito, M. Mori, J. Am. Chem. Soc. 2000, 122, 2371; b) Y. Sato, M. Takimoto, K. Hayashi, T. Katsuhara, K. Takagi, M. Mori. J. Am. Chem. Soc. 1994, 116, 9771; c) K. Shibata, M. Kimura, M. Shimizu, Y. Tamaru, Org. Lett. 2001, 3, 2181; d) K. K. Majumdar, C.-H. Cheng, Org. Lett. 2000, 2, 2295; e) Y.C. Huang, K. K. Majumdar, C.-H. Cheng, J. Org. Chem. 2002, 67, 1682; f) E. Oblinger, J. Montgomery, J. Am. Chem. Soc. 1997, 119, 9065; g) M. V. Chevliakov, J. Montgomery, J. Am. Chem. Soc. 1999, 121, 11139; h) K. K. D. Amarasinghe, J. Montgomery, J. Am. Chem. Soc. 2002, 124, 9366.
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39. 13CNMR spectra of compounds 1, 2, 4-6 13-18, 21, and 23 are available in the Supporting Information.
40. CCDC-188743 (9) and CCDC-188742 (22) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit @ccdc.cam.ac.uk).
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