Cross coupling of vinyl triflates and alkyl Grignard reagents catalyzed by niekel(0)-complexes

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3101-3104

  Busacca, Carl A ^a   Eriksson, Magnus C ^a   Fiaschi, Rita ^a,b  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

^b Via Bonanno 56100   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

NICKEL COMPLEX; REAGENT;

ARTICLE; CATALYSIS; REACTION ANALYSIS;

EID: 0033574445     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00439-6     Document Type: Article

References (20)

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12. For examples using manganese catalysis, see Fugami, K.; Oshima, K.; Utimoto, K. Chemistry Lett. 1987, 2203.
13. The triflates were prepared following the procedure in Stang, P.J.; Treptow, W. Synthesis 1980, 283.
14. 3): 148.05, 140.32, 133.40, 128.78, 127.86, 112.98, 35.40, 30.76, 22.77, 14.32. GCMS, m/z: 194(2), 152(100), 137(10), 117(20), 115(20).
15. 2dppb was prepared according to Frauenrath, H.; Wille, A.; Tomm, S. Synthesis 1998, 305.
16. 5Br and Mg(0)) was coupled with triflate 2 as shown, 72%D incorporation was found in the reduced species (reproducible, 2 experiments). Thus, the majority of the reduction occurs via (equation presented) βhydride elimination. Experiments using deuterated solvents, however, have not shown label incorporation, and the source of the remaining reduction is unknown.
17. Barton, D.H.R.; Bashiardes, G.; Fourrey, J.-L. Tetrahedron 1988, 44, 147.
18. 2dppe is .3°, see Busby, R.; Hursthouse, M.B.; Jarret, P.S.; Lehmann, C.W.; Abdul Malik, K.M.; Phillips, C. J. Chem. Soc. Dalton Trans. 1993, 3767.
19. 2dppf is 99.1°, see reference 7.
20. Titration was performed according to Kofron, W.G.; Baclawski, L.M. J. Org. Chem. 1976, 41, 1879.