Highly Selective Pd-Catalyzed Direct C-F Bond Arylation of Polyfluoroarenes.

Org Lett

Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , China.

Published: May 2018

A directing-group-free palladium-catalyzed direct arylation of simple polyfluoroarenes with arylboronic acids through selective C-F bond activation is described. The combination of Pd(OAc) with BrettPhos was identified as an efficient catalytic system to promote the reaction with high regioselectivity and broad substrate scope. Preliminary mechanistic studies reveal that the oxidative addition of Pd to the C-F bond is involved in the catalytic cycle.

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http://dx.doi.org/10.1021/acs.orglett.8b00692DOI Listing

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