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Synthesis of Substituted Cyclopropanecarboxylates via Room Temperature Palladium-Catalyzed α-Arylation of Reformatsky Reagents

Stephen N. Greszler*, Geoff T. Halvorsen and Eric A. Voight

*Centralized Lead Optimization - Discovery Chemistry & Technology, AbbVie, Inc., 1 N. Waukegan Road, North Chicago, Illinois 60064, United States, Email:

S. N. Greszler, G. T. Halvorsen, E. A. Voight, Org. Lett., 2017, 19, 2490-2493.

DOI: 10.1021/acs.orglett.7b00707

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A mild, room temperature palladium-catalyzed cross-coupling of aromatic and heteroaromatic halides with Reformatsky reagents derived from 1-bromocyclopropanecarboxylates provides α-arylated products. The method tolerates a broad range of functionalities and dramatically shortens many of the existing routes to access widely used 1,1-disubstituted cyclopropanecarboxylate derivatives.

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Key Words

Negishi coupling, cyclopropanes

ID: J54-Y2017