Synthesis of N-Difluoromethyl Carbonyl Compounds from N-Difluoromethylcarbamoyl Fluorides
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2024)
摘要
Fluorinated small molecules are commonly used in functional small-molecule chemistry, and N-difluoromethyl (N-CF2H) compounds are particularly intriguing due to their unique and unexplored physiochemical properties. However, despite limited progress, a general methodological approach to the synthesis of N-CF2H compounds remains elusive. Here, guided by computation, we present a simple and practical protocol to access N-CF2H amides and related carbonyl derivatives. The protocol involves a one-pot conversion of thioformamides through desulfurization-fluorination and acylation, providing N-difluoromethylcarbamoyl fluoride building blocks that can be further diversified to a variety of unexplored N-CF2H carbonyl compounds with rich functionality. Additionally, preliminary studies on their properties and stability showcased their potential application in pharmaceuticals and agrochemicals.
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关键词
Difluoromethyl,carbamoyl fluorides,building blocks,amides,pharmaceutical
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