Iron-Catalyzed Highly para-Selective Difluoromethylation of Arenes.

J Am Chem Soc

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China.

Published: December 2020

Direct functionalization of a C-H bond at either the meta or para position by only changing the catalyst system poses a significant challenge. We herein report the [Fe(TPP)Cl]-enabled, selective, C-H difluoromethylation of arenes using BrCFCOEt as the difluoromethylation source, which successfully altered the selectivity from the meta to the para position. A preliminary mechanistic study revealed the iron porphyrin complex not only activated the aromatic ring but also induced para selectivity due to the influence of ligand sterics.

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http://dx.doi.org/10.1021/jacs.0c09545DOI Listing

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