Copper-Catalyzed Defluorinative Borylation and Silylation of gem-Difluoroallyl Groups

Trevor W. Butcher, Jonathan L. Yang and John F. Hartwig*

*Department of Chemistry, University of California, Berkeley, California 94720, United States, Email: jhartwigberkeley.edu

T. W. Butcher, J. L. Yang, J. F. Hartwig, Org. Lett., 2020, 22, 6805-6809.

DOI: 10.1021/acs.orglett.0c02321

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Abstract

A copper-catalyzed formal S_N2' defluorinative borylation of 3-substituted 3,3-difluoropropenes provides 3-fluoroallylboronic esters in high yields with excellent Z:E ratios. The primary 3-fluoroallylboronic esters undergo several synthetic sequences involving sigmatropic rearrangements, S_E2' substitutions, and S_N2' substitutions to give tertiary allylic fluorides.

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Key Words

alkenyl fluorides, allyl boronates, allyl alcohols

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ID: J54-Y2020