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CuBr-mediated radical cascade difluoroacetamidation of acrylamides using α,α-difluoro-α-(TMS)-acetamides

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Radical cascade difluoroacetamidation of N-(arylsulfonyl)acrylamides with α,α-difluoro-α-(TMS)-acetamides has been achieved for the first time. This CuBr-mediated transformation is easy to perform, generates high yields and shows a good substrate scope.… Click to show full abstract

Radical cascade difluoroacetamidation of N-(arylsulfonyl)acrylamides with α,α-difluoro-α-(TMS)-acetamides has been achieved for the first time. This CuBr-mediated transformation is easy to perform, generates high yields and shows a good substrate scope. This cascade reaction proceeds via difluoroacetamidation, aryl migration and desulfonylation. The products can be readily transformed into synthetically useful compounds such as difluorofunctionalized esters and alcohols in excellent yields.

Keywords: difluoro tms; radical cascade; tms acetamides; cascade; cascade difluoroacetamidation; difluoroacetamidation

Journal Title: Organic chemistry frontiers
Year Published: 2017

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