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Palladium-Catalyzed Cross-Coupling of Cyclopropylmagnesium Bromide with Aryl Bromides Mediated by Zinc Halide Additives

Chutian Shu, Kanwar Sidhu, Li Zhang, Xiao-jun Wang, Dhileepkumar Krishnamurthy and Chris H. Senanayake

*Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877, Email: xiao-jun.wangboehringer-ingelheim.com

C. Shu, K. Sidhu, L. Zhang, X.-j. Wang, D. Krishnamurthy, C. H. Senanayake, J. Org. Chem., 2010, 75, 6677-6680.

DOI: 10.1021/jo100983c (free Supporting Information)


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Abstract

The Pd-catalyzed cross-coupling of aryl bromides or triflates with cyclopropylmagnesium bromide in the presence of substoichiometric amounts of zinc bromide produces cyclopropyl arenes in very good yields. The cross-coupling of other alkyl, cycloalkyl, and aryl Grignard reagents with aryl bromides under the same conditions gives the corresponding substituted arenes in good yields.


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Key Words

cyclopropanes, substituted arenes


ID: J42-Y2010-2690