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