Alternatives to vinyl triflates for cross-coupling with arylboronic acids

Synlett

Volumn , Issue 4, 1999, Pages 471-473

  Huffman, Mark A ^a   Yasuda, Nobuyoshi ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Boronic acid; Carbapenem; Cross coupling; Nickel; Palladium

Indexed keywords

BORONIC ACID DERIVATIVE; CARBAPENEM DERIVATIVE; MESYLIC ACID; NICKEL; PALLADIUM; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032894460     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2643     Document Type: Article

References (17)

1. (a) Oh-e, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201-2208.
2. (b) Fu, J.-m.; Snieckus, V. Tetrahedron Lett. 1990, 31, 1665-1668.
3. (a) Yasuda, N.; Xavier, L.; Rieger, D. L.; Li, Y.; DeCamp, A. E.; Dolling, U.-H. Tetrahedron Lett. 1993, 34, 3211-3214.
4. (b) Decamp, A.; Dolling, U.-H.; Li, Y.; Rieger, D. L.; Yasuda, N.; Xavier, L. C. U.S. Patent 5,338,875, 1994.
5. The vinyl fluorosulfonate group has been reported as a triflate replacement in Stille-type couplings for cephalosporin synthesis. Roth, G. P.; Sapino, C. Tetrahedron Lett. 1991, 32, 4073-4076.
6. (a) Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6163-6165.
7. (b) Melillo, D. G.; Shinkai, I.; Liu, T.; Ryan, K.; Sletzinger, M. Tetrahedron Lett. 1980, 21, 2783-2786.
8. Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1060-1065.
9. dppf = 1,1′-Bis(diphenylphosphino)ferrocene; dppp = 1,3-Bis(diphenylphosphino)propane; dppb = 1,4-Bis(diphenylphosphino)butane; dba = Dibenzylideneacetone.
10. 5S: C, 59.24; H, 6.21;. Found: C, 59.16; H, 6.28. The data for compounds 6 and 7 are listed in note 12. All other compounds gave data in accordance with values reported in the literature.
11. D'Aniello, M. J. Jr.; Barefield, E. K. J. Am. Chem. Soc. 1978, 100, 1474-1481.
12. 2 and dppp in 1-propanol. Van Hecke, G. R.; Horrocks, W. D. Jr. Inorg. Chem. 1966, 5, 1968-1974. Depending on the amount of water present during preparation, we obtained either light purple or dark red crystals which were equal in activity.
13. An alternative in-situ formation of Ni(0) from Ni(II) and n-BuLi has been reported for cross-coupling of aryl chlorides, (a) Saito, S.; Sakai, M.; Miyaura, N. Tetrahedron Lett. 1996, 37, 2993-2996. For related nickel-catalyzed couplings, see also:
14. (b) Kobayashi, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 8531-8534.
15. (c) Indolese, A.F.; Tetrahedron Lett. 1997, 38, 3153-3516.
16. Wallow, T. I.; Novak, B. M. J. Org. Chem. 1994, 59, 5034-5037.
17. 6Si: C, 64.34; H, 6.56; N, 5.36. Found: C, 64.35; H, 6.46; N, 5.32.