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N-Difluoromethylation of N-pyridyl-substituted anilines with ethyl bromodifluoroacetate†
Pui Ying Choy,Kin Boon Gan
Organic & Biomolecular Chemistry Pub Date : 02/09/2022 00:00:00 , DOI:10.1039/D2OB00119E
Abstract

A general protocol for N-difluoromethylation of aniline derivatives is developed. Commercially available ethyl bromodifluoroacetate serves as a difluorocarbene source in the presence of a base. This carbene surrogate is attractive owing to its favorable stability, environmental friendliness and inexpensiveness. This reaction system features notable operational simplicity (bench top-grade solvents can be used without any pre-drying and do not require inert atmosphere protection). A wide range of functional groups in aniline derivatives are well-tolerated, and good-to-excellent product yields are generally obtained.

Graphical abstract: N-Difluoromethylation of N-pyridyl-substituted anilines with ethyl bromodifluoroacetate
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