Palladium-catalyzed cross-coupling reaction of organobismuth compounds with aryl and alkenyl chlorides

Synlett

Volumn , Issue 11, 2004, Pages 1921-1924

  Yamazaki, Osamu ^a   Tanaka, Toshifumi ^b   Shimada, Shigeru ^a   Suzuki, Yohichi ^b   Tanaka, Masato ^a,c  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b NIHON UNIVERSITY   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Bismuth; Cross coupling; Hypervalent; Organometallic reagents; Palladium

Indexed keywords

BISMUTH DERIVATIVE; CHLORIDE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION;

EID: 4544283952     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831298     Document Type: Article

References (37)

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7. For recent works, see: (a) Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2002, 41, 609. (b) Gstöttmayer, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1363. (c) Schareina, T.; Kempe, R. Angew. Chem. Int. Ed. 2002, 41, 1521. (d) Schnyder, A.; Indolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem. Int. Ed. 2002, 41, 3668. (e) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem. Int. Ed. 2002, 41, 4120. (f) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866. (g) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856. (h) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (i) Roca, F. X.; Richards, C. J. Chem. Commun. 2003, 3002. (j) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
8. For recent works, see: (a) Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2002, 41, 609. (b) Gstöttmayer, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1363. (c) Schareina, T.; Kempe, R. Angew. Chem. Int. Ed. 2002, 41, 1521. (d) Schnyder, A.; Indolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem. Int. Ed. 2002, 41, 3668. (e) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem. Int. Ed. 2002, 41, 4120. (f) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866. (g) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856. (h) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (i) Roca, F. X.; Richards, C. J. Chem. Commun. 2003, 3002. (j) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
9. For recent works, see: (a) Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2002, 41, 609. (b) Gstöttmayer, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1363. (c) Schareina, T.; Kempe, R. Angew. Chem. Int. Ed. 2002, 41, 1521. (d) Schnyder, A.; Indolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem. Int. Ed. 2002, 41, 3668. (e) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem. Int. Ed. 2002, 41, 4120. (f) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866. (g) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856. (h) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (i) Roca, F. X.; Richards, C. J. Chem. Commun. 2003, 3002. (j) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
10. For recent works, see: (a) Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2002, 41, 609. (b) Gstöttmayer, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1363. (c) Schareina, T.; Kempe, R. Angew. Chem. Int. Ed. 2002, 41, 1521. (d) Schnyder, A.; Indolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem. Int. Ed. 2002, 41, 3668. (e) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem. Int. Ed. 2002, 41, 4120. (f) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866. (g) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856. (h) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (i) Roca, F. X.; Richards, C. J. Chem. Commun. 2003, 3002. (j) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
11. For recent works, see: (a) Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2002, 41, 609. (b) Gstöttmayer, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1363. (c) Schareina, T.; Kempe, R. Angew. Chem. Int. Ed. 2002, 41, 1521. (d) Schnyder, A.; Indolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem. Int. Ed. 2002, 41, 3668. (e) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem. Int. Ed. 2002, 41, 4120. (f) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866. (g) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856. (h) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (i) Roca, F. X.; Richards, C. J. Chem. Commun. 2003, 3002. (j) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
12. For recent works, see: (a) Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2002, 41, 609. (b) Gstöttmayer, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1363. (c) Schareina, T.; Kempe, R. Angew. Chem. Int. Ed. 2002, 41, 1521. (d) Schnyder, A.; Indolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem. Int. Ed. 2002, 41, 3668. (e) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem. Int. Ed. 2002, 41, 4120. (f) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866. (g) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856. (h) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (i) Roca, F. X.; Richards, C. J. Chem. Commun. 2003, 3002. (j) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
13. For recent works, see: (a) Fürstner, A.; Leitner, A. Angew. Chem. Int. Ed. 2002, 41, 609. (b) Gstöttmayer, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1363. (c) Schareina, T.; Kempe, R. Angew. Chem. Int. Ed. 2002, 41, 1521. (d) Schnyder, A.; Indolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem. Int. Ed. 2002, 41, 3668. (e) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew. Chem. Int. Ed. 2002, 41, 4120. (f) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866. (g) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856. (h) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127. (i) Roca, F. X.; Richards, C. J. Chem. Commun. 2003, 3002. (j) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
14. For reviews on the utilization of organobismuth compounds in organic synthesis, see: (a) Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249. (b) Suzuki, H.; Matano, Y. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic and Professional: London, 1998, Chap. 6. (c) Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683. (d) Organobismuth Chemistry; Suzuki, H.; Matano, Y., Eds.; Elsevier: Amsterdam, 2001. (e) Matano, Y. Yuki Gosei Kagaku Kyokaishi 2001, 59, 834; Chem. Abstr. 2001, 135, 371248j.
15. For reviews on the utilization of organobismuth compounds in organic synthesis, see: (a) Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249. (b) Suzuki, H.; Matano, Y. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic and Professional: London, 1998, Chap. 6. (c) Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683. (d) Organobismuth Chemistry; Suzuki, H.; Matano, Y., Eds.; Elsevier: Amsterdam, 2001. (e) Matano, Y. Yuki Gosei Kagaku Kyokaishi 2001, 59, 834; Chem. Abstr. 2001, 135, 371248j.
16. For reviews on the utilization of organobismuth compounds in organic synthesis, see: (a) Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249. (b) Suzuki, H.; Matano, Y. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic and Professional: London, 1998, Chap. 6. (c) Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683. (d) Organobismuth Chemistry; Suzuki, H.; Matano, Y., Eds.; Elsevier: Amsterdam, 2001. (e) Matano, Y. Yuki Gosei Kagaku Kyokaishi 2001, 59, 834; Chem. Abstr. 2001, 135, 371248j.
17. For reviews on the utilization of organobismuth compounds in organic synthesis, see: (a) Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249. (b) Suzuki, H.; Matano, Y. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic and Professional: London, 1998, Chap. 6. (c) Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683. (d) Organobismuth Chemistry; Suzuki, H.; Matano, Y., Eds.; Elsevier: Amsterdam, 2001. (e) Matano, Y. Yuki Gosei Kagaku Kyokaishi 2001, 59, 834; Chem. Abstr. 2001, 135, 371248j.
18. For reviews on the utilization of organobismuth compounds in organic synthesis, see: (a) Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249. (b) Suzuki, H.; Matano, Y. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic and Professional: London, 1998, Chap. 6. (c) Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683. (d) Organobismuth Chemistry; Suzuki, H.; Matano, Y., Eds.; Elsevier: Amsterdam, 2001. (e) Matano, Y. Yuki Gosei Kagaku Kyokaishi 2001, 59, 834; Chem. Abstr. 2001, 135, 371248j.
19. For reviews on the utilization of organobismuth compounds in organic synthesis, see: (a) Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249. (b) Suzuki, H.; Matano, Y. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic and Professional: London, 1998, Chap. 6. (c) Elliott, G. I.; Konopelski, J. P. Tetrahedron 2001, 57, 5683. (d) Organobismuth Chemistry; Suzuki, H.; Matano, Y., Eds.; Elsevier: Amsterdam, 2001. (e) Matano, Y. Yuki Gosei Kagaku Kyokaishi 2001, 59, 834; Chem. Abstr. 2001, 135, 371248j.
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35. 3 after complete decomposition.
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37. 3 is slow at r.t. and is not complete, and seems to reach equilibrium at about 60% conversion.