Sonogashira coupling reaction with diminished homocoupling

Organic Letters

Volumn 5, Issue 11, 2003, Pages 1841-1844

  Elangovan, Arumugasamy ^a   Wang, Yu Hsiang ^a   Ho, Tong Ing ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ARGON; HYDROGEN; NITROGEN; OXYGEN;

ARTICLE; ATMOSPHERE; CATALYST; CHEMICAL REACTION; COUPLING FACTOR; QUANTUM YIELD; SONOGASHIRA REACTION; SYNTHESIS;

EID: 0041364065     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034320+     Document Type: Article

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27. For example, see: (a) Van Overmeiere, I. V.; Boldin, S. A.; Venkataraman, K.; Zisling, R.; De Jonghe, S. Van Calenbergh, S.; De Keukeleire, D.; Futerman, A. H.; Herdewijn, P. J. Med. Chem. 2000, 43, 4189-4199. (b) Leonard, K. A.; Nelen, M. I.; Anderson, L. T.; Gibson, S. L.; Hilf, R.; Detty, M. R. J. Med. Chem. 1999, 42, 3942-3952. (c) Walker, W. H., IV.; Rokita, S. E. J. Org. Chem. 2003, 68, 1563-1566.
28. For recent general modifications of Sonogashira coupling, see: (a) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. (b) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411-1414. (c) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649-651. (d) Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897-900. (d) Bohm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679-3681. (e) Radhakrishnan, U.; Stang, P. J. Org. Lett. 2001, 3, 859-860. (f) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756-757. (g) Kölhoffer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056-1058. (h) For recent highlights on the usefulness and limitations of Sonogashira reactions, see: Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566-1568.
29. For recent general modifications of Sonogashira coupling, see: (a) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. (b) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411-1414. (c) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649-651. (d) Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897-900. (d) Bohm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679-3681. (e) Radhakrishnan, U.; Stang, P. J. Org. Lett. 2001, 3, 859-860. (f) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756-757. (g) Kölhoffer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056-1058. (h) For recent highlights on the usefulness and limitations of Sonogashira reactions, see: Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566-1568.
30. For recent general modifications of Sonogashira coupling, see: (a) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. (b) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411-1414. (c) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649-651. (d) Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897-900. (d) Bohm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679-3681. (e) Radhakrishnan, U.; Stang, P. J. Org. Lett. 2001, 3, 859-860. (f) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756-757. (g) Kölhoffer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056-1058. (h) For recent highlights on the usefulness and limitations of Sonogashira reactions, see: Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566-1568.
31. For recent general modifications of Sonogashira coupling, see: (a) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. (b) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411-1414. (c) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649-651. (d) Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897-900. (d) Bohm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679-3681. (e) Radhakrishnan, U.; Stang, P. J. Org. Lett. 2001, 3, 859-860. (f) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756-757. (g) Kölhoffer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056-1058. (h) For recent highlights on the usefulness and limitations of Sonogashira reactions, see: Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566-1568.
32. For recent general modifications of Sonogashira coupling, see: (a) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. (b) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411-1414. (c) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649-651. (d) Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897-900. (d) Bohm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679-3681. (e) Radhakrishnan, U.; Stang, P. J. Org. Lett. 2001, 3, 859-860. (f) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756-757. (g) Kölhoffer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056-1058. (h) For recent highlights on the usefulness and limitations of Sonogashira reactions, see: Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566-1568.
33. For recent general modifications of Sonogashira coupling, see: (a) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. (b) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411-1414. (c) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649-651. (d) Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897-900. (d) Bohm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679-3681. (e) Radhakrishnan, U.; Stang, P. J. Org. Lett. 2001, 3, 859-860. (f) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756-757. (g) Kölhoffer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056-1058. (h) For recent highlights on the usefulness and limitations of Sonogashira reactions, see: Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566-1568.
34. For recent general modifications of Sonogashira coupling, see: (a) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. (b) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411-1414. (c) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649-651. (d) Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897-900. (d) Bohm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679-3681. (e) Radhakrishnan, U.; Stang, P. J. Org. Lett. 2001, 3, 859-860. (f) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756-757. (g) Kölhoffer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056-1058. (h) For recent highlights on the usefulness and limitations of Sonogashira reactions, see: Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566-1568.
35. For recent general modifications of Sonogashira coupling, see: (a) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. (b) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411-1414. (c) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649-651. (d) Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897-900. (d) Bohm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679-3681. (e) Radhakrishnan, U.; Stang, P. J. Org. Lett. 2001, 3, 859-860. (f) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756-757. (g) Kölhoffer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056-1058. (h) For recent highlights on the usefulness and limitations of Sonogashira reactions, see: Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566-1568.
36. For recent general modifications of Sonogashira coupling, see: (a) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731. (b) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411-1414. (c) Mori, A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett 2001, 649-651. (d) Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897-900. (d) Bohm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679-3681. (e) Radhakrishnan, U.; Stang, P. J. Org. Lett. 2001, 3, 859-860. (f) Mori, A.; Ahmed, M. S. M.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756-757. (g) Kölhoffer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056-1058. (h) For recent highlights on the usefulness and limitations of Sonogashira reactions, see: Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566-1568.
37. +) 222.123; (M + 1) 223.1322.
38. Nishikawa, S.; Sato, M.; Kojima, H.; Suzuki, C.-e.; Yamada, N.; Inagaki, M.; Kashimura, N.; Mizuno, H. J. Agric. Food Chem. 1996, 44, 1337-134.
39. 1H NMR: δ (ppm) = 7.48-7.51 (m, 2H); 7.45 (d, 2H, J = 8.8 Hz); 7.32-7.23 (m, 3H); 6.86 (d, 2H, J = 8.8 Hz). The term "original method" refers to the method given in ref 3b (under nitrogen atmosphere), and all reactions under original method were done after flushing the r