Organic Chemistry Portal

Abstracts

Search:

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


see article for more reactions

Abstract

A copper-catalyzed formal SN2' 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, SE2' substitutions, and SN2' substitutions to give tertiary allylic fluorides.

see article for more examples



Key Words

alkenyl fluorides, allyl boronates, allyl alcohols


ID: J54-Y2020