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Cobalt-Catalyzed Cross-Coupling of Grignards with Allylic and Vinylic Bromides: Use of Sarcosine as a Natural Ligand

Rok Frlan, Matej Sova, Stanislav Gobec, Gaj Stavber and Zdenko Časar*

*Faculty of Pharmacy, University of Ljubljana, Aškerčeva 7, 1000 Ljubljana, Slovenia, Email: zdenko.casarsandoz.com

R. Frlan, M. Sova, S. Gobec, G. Stavber, Z. Časar, J. Org. Chem., 2015, 80, 7803-7809.

DOI: 10.1021/acs.joc.5b01156 (free Supporting Information)


 

Abstract

Sarcosine is an excellent ligand for cobalt-catalyzed carbon-carbon cross-coupling of Grignard reagents with allylic and vinylic bromides. The system performs efficiently when phenyl and benzyl Grignards are coupled with alkenyl bromides. Notably, previously unachievable Co-catalyzed coupling of allylic bromides with Grignards to linearly coupled α-products was also realized.

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Key Words

allylation (of arenes), vinylation (of arenes), benzylation


ID: J42-Y2015