Synthesis and Suzuki Reactions of N-Heterocyclic Carbene Difluoro(aryl)-boranes.

Org Lett

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.

Published: July 2015

Readily available NHC-arylboranes (NHC-BH2Ar) are converted in high yield to stable NHC-difluoro(aryl)boranes (NHC-BF2Ar) by treatment with 2 equiv of 1-chloromethyl-4-fluoro-1,4-diazonia-bicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor). In turn, the NHC-difluoro(aryl)boranes participate directly in Suzuki reactions under conditions previously used for anionic trifluoroborate salts. Accordingly, NHC-difluoroboranes are a new class of stable precursors for Suzuki reactions.

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http://dx.doi.org/10.1021/acs.orglett.5b01101DOI Listing

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