Stereoselective Rhodium(I)-Catalyzed C–F Bond Arylation of Tri- and Tetrasubstituted <i>gem</i>-Difluoroalkenes with Boronic Acids

Abstract

We herein describe a highly diastereoselective rhodium(I)-catalyzed C–F bond functionalization of gem -difluoroalkenes with arylboronic acids. In contrast to previously developed Pd(II)- and Pd(0)-catalyzed methods, the Rh(I)/BINAP catalytic system enabled the C–F bond arylation of both trisubstituted β,β-difluorostyrenes and tetrasubstituted β,β-difluoroacrylates in >99:1 dr toward the synthesis of valuable monofluoroalkenes. Experimental and computational studies suggested a plausible migratory insertion/β-F elimination mechanism with the [Rh(I)-Ar] species.

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