4.8 Article

Visible Light/Tertiary Amine Promoted Synergistic Hydroxydifluoroacetamidation of Unactivated Alkenes under Air

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ORGANIC LETTERS
卷 23, 期 2, 页码 617-622

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c04216

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资金

  1. National Natural Science Foundation of China [22078299]
  2. Zhejiang Provincial Natural Science Foundation of China [LQ20B060007, LY21B060005]
  3. College of Pharmaceutical Sciences, Zhejiang University of Technology
  4. Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals

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This efficient and novel method involves regioselective hydroxydifluoroacetamidation of alkenes with bromodifluoroacetamides through a tandem radical pathway mediated by photoredox catalysis under metal-free conditions. The reaction, using Rhodamine 6G as the photocatalyst, produces a series of alpha,alpha-difluoro-gamma-hydroxyacetamides in moderate to excellent yields, demonstrating the advantages of low-cost photocatalyst, readily available starting materials, synthetic convenience, and wide functional group compatibility.
An efficient and novel method for regioselective hydroxydifluoroacetamidation of alkenes with bromodifluor-oacetamides has been achieved via a tandem radical pathway mediated by photoredox catalysis under metal-free conditions. This transformation proceeded smoothly in the presence of Rhodamine 6G, affording a series of alpha,alpha-difluoro-gamma-hydroxyacetamides in moderate to excellent yields. The significant advantages of this protocol are the low-cost photocatalyst, readily available starting materials, synthetic convenience, and wide functional group compatibility.

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