Control of reactive site in Palladium-Catalyzed grignard Cross-Coupling of arenes containing both bromide and triflate

Tetrahedron Letters

Volumn 38, Issue 40, 1997, Pages 7087-7090

  Kamikawa, Takashi ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0030807343     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01655-9     Document Type: Article

References (22)

1. For reviews on palladium-or nickel-catalyzed cross-coupling reactions: (a) Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 5, pp 161-240.
2. (b) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1995; pp. 209-243.
3. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
4. (d) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
5. (e) Mitchell, T. N. Synthesis 1992, 803-815.
6. (f) Ritter, K. Synthesis 1993, 735-762.
7. 4 in DMF: Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810-1817.
8. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486.
9. In the palladium-catalyzed reaction of 4-bromophenyl triflate with an alkylborane, bromide undergoes cross-coupling preferentially: Oh-e, T.; Miyaura, N.; Suzuki, A. Synlett 1990, 221-223.
10. Carbonylation of 4-bromophenyl triflate in the presence of palladium-dppf catalyst takes place at triflate selectively: Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1986, 27, 3931-3934.
11. For recent examples of the Grignard cross-coupling of aryl triflates: (a) Sengupta, S.; Leite, M.; Raslan, D. S.; Quesnelle, C.; Snieckus, V. J. Org. Chem. 1992, 57, 4066-4068.
12. (b) Kamikawa, T.; Hayashi, T. Synlett 1997, 163-164.
13. 2(dppp) for the cross-coupling of aryl triflates has been observed in the reaction of sterically congested aryl triflates with aryl Grignard reagents forming biaryls: ref 6b.
14. The acceleration effect of lithium chloride or bromide has been first reported in cross-coupling of vinyl triflates with organostannanes: Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033-3040.
15. In the palladium-catalyzed Grignard cross-coupling, the effect of lithium bromide has been also observed: (a) Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101-9102.
16. (b) Kamikawa, T.; Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1996, 37, 3161-3164.
17. For the effects of lithium bromide on the oxidative addition of aryl triflates to palladium(0): Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531-9541.
18. 2: Uozumi, Y.; Kitayama, K.; Hayashi, T.; Yanagi, K.; Fukuyo, E. Bull. Chem. Soc. Jpn. 1995, 68, 713-722.
19. For meo-mop: (a) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887-9888.
20. (b) Uozumi, Y. Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945-1948.
21. 3, 109 MHz): δ -9.40 (d, J = 52.5 Hz, 1 P), 11.17 (d, J= 52.5 Hz, 1 P).
22. 3, 161 MHz): δ 23.32 (s).