Ruthenium(II)-Catalyzed α-Fluoroalkenylation of Oxime Ethers with -Difluorostyrenes C-H Activation and C-F Cleavage.

J Org Chem

Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.

Published: October 2020

A novel route for ruthenium(II)-catalyzed α-fluoroalkenylation of oxime ethers with -difluorostyrenes C-H activation and C-F cleavage has been developed for the first time. Notably, the alkenyl units of products exhibit exclusive Z-configuration. This reaction features a broad substrate scope and good functional group tolerance. A plausible reaction mechanism is confirmed by an available cycloruthenated intermediate. Besides, the -methyl oximyl-directing group can be readily removed to access the α-fluoroalkenylated acetophenones.

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http://dx.doi.org/10.1021/acs.joc.0c01842DOI Listing

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