Palladium and nickel catalysed Suzuki cross-coupling of sterically hindered aryl bromides with phenylboronic acid

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2487-2490

  Griffiths, Clare ^a   Leadbeater, Nicholas E ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Biaryls; Nickel; Palladium; Steric hindrance; Suzuki cross coupling

Indexed keywords

BORONIC ACID DERIVATIVE; BROMIDE; NICKEL COMPLEX; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; SYNTHESIS;

EID: 0034175562     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00186-6     Document Type: Article

References (17)

1. Tsuji, J. Palladium Reagents and Catalysis; Wiley: New York, 1995.
2. Stanforth, S. P. Tetrahedron 1998, 54, 263.
3. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
4. Suzuki, A. Pure Appl. Chem. 1994, 66, 213.
5. Wanatabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207.
6. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 1998, 37, 3387.
7. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
8. 3, 250 MHz): δ 2.0 (s, 6H), 7.21 (m, 2H), 7.26 (m, 2H), 7.33 (m, 2H), 7.38 (m, 1H), 7.41(m, 1H). MS (ES) m/z 182 (calcd 182.2).
9. Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 2956.
10. 2-Ethyl-6-methylbromobenzene was prepared by the published procedure (Bultsma, T.; Mejer, J. F.; Pauli, F. I.; Ramacker, J. P.; Nauta, W. T. Eur. J. Med. Chem.-Chim. Ther. 1977, 12, 427).
11. 3, 250 MHz): δ 1.23 (t, 3H), 2.25 (s, 3H), 2.75 (q, 2H), 7.21 (m, 2H), 7.25 (m, 2H), 7.35 (m, 2H), 7.49 (m, 1H), 7.51 (m, 1H). MS (ES) m/z 196 (calcd 196.2).
12. 3, 250 MHz): δ 7.4 (m, 4H), 7.16 (m, 10H). MS (ES) m/z 230 (calcd 230.3). Mp 56°C (lit. 56-58°C).
13. 3, 250 MHz): δ 8.42 (m, 1H), 7.95 (m, 2H), 7.62 (m, 2H), 7.51 (m, 4H), 7.42 (m, 3H), 7.3 (m, 2H). MS (ES) m/z 254 (calcd 254.3). Mp 154°C (lit 153-155°C).
14. Kamikawa, T.; Hayashi, T. Synlett 1997, 207.
15. Johnson, M. G.; Foglesong, R. J. Tetrahedron Lett. 1997, 38, 7002.
16. 2 has been used in cross-coupling reactions before with some considerable success. See: Indolese, A. F. Tetrahedron Lett. 1997, 38, 3513.
17. 3 route. Yields of the products are shown in Table 4.