Cu(I)-catalyzed substitution reactions of activated vinyl triflates with functionalized organozinc reagents

Tetrahedron Letters

Volumn 40, Issue 15, 1999, Pages 2871-2874

  Lipshutz, Bruce H ^a   Vivian, Randall W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; ORGANIC COMPOUND; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY;

EID: 0033537814     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00355-X     Document Type: Article

References (18)

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2. Posner, G.H. Org. React. (N.Y.) 1975, 22, 353.
3. Lipshutz, B.H.; Woo, K.; Gross, T.; Buzard, D.J.; Tirado, R. Synlett 1997, 477.
4. Lipshutz, B.H. Acc. Chem. Res. 1997, 30, 277.
5. Ritter, K. Synthesis 1993, 735.
6. For CuCN•2LiCl-catalyzed alkylations of zinc reagents with allylic halides and alkynyl bromides, see: Knochel, P.; Yeh, M.C.P.; Berk, S.C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
7. McMurry, J.E.; Scott, W.J. Tetrahedron Lett. 1980, 21, 4313.
8. Knochel, P.; Singer, R.D. Chem. Rev. 1993, 93, 2117.
9. Lipshutz, B.H. In Organometallics in Synthesis: A Manual, Schlosser, M. Ed., Wiley, 1994, pp 283-382.
10. Malmberg, H.; Nilsson, M.; Ullenius, C. Tetrahedron Lett. 1982, 23, 3823.
11. (a) Bertz, S.H.; Eriksson, M.; Miao, G.; Snyder, J.P. J. Am. Chem. Soc. 1996, 118, 10906;
12. (b) Knochel, P. Jones, P.; Reddy, C. K. Tetrahedron 1998, 54, 1471.
13. This reaction (Table 1, entry 1) required 1.25 h, instead of the 25 min needed in the presence of 3 mol % CuCN•2LiCl.
14. (a) Farina, V.; Baker, S.R.; Hauck, S.I. J. Org. Chem. 1989, 54, 4962; olefin migration, observed previously in Pd(0)-based couplings, was not seen in these copper-catalyzed reactions;
15. (b) Mu, YQ.; Gibbs, R.A.; Eubanks, L.M.; Poulter, C.D. ibid. 1996, 61, 8010.
16. (a) Knochel, P.; Rottlander, M. J. Org. Chem. 1998, 63, 203;
17. (b) Subramanian, L.R.; Bentz, H.; Hanack, M. Synthesis 1973, 293.
18. 3 238.1569, found 238.1565.