4.7 Article

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

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 4, Issue 8, Pages 1606-1610

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7qo00209b

Keywords

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Funding

  1. National Natural Science Foundation of China [21372072, 21421004, 21561162003, 21672059]
  2. Eastern Scholar Distinguished Professor Program
  3. Fundamental Research Funds for the Central Universities

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Radical cascade difluoroacetamidation of N-(arylsulfonyl) acrylamides with alpha, alpha-difluoro-alpha-(TMS)-aceta-mides 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.

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