4.8 Article

Palladium-Catalyzed Radical Cascade lododifluoromethylation/Cyclization of 1,6-Enynes with Ethyl Difluoroiodoacetate

Journal

ORGANIC LETTERS
Volume 17, Issue 17, Pages 4280-4283

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02068

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Funding

  1. National Science Foundation [NSF21272101, 21472074, 21472073]
  2. 111 Project [J1103307]
  3. Program for Changjiang Scholars and Innovative Research Team in University [IRT1138]

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A novel and convenient Pd-catalyzed radical cascade iododifluoromethylation/cyclization of 1,6-enynes with ethyl difluoroiodoacetate is demonstrated. The proposed transformation presents high stereoselectivity under mild and facile reaction conditions, thereby allowing an efficient access to a variety of iodine-containing difluoromethylated pyrrolidines. A possible radical pathway for the transformation is proposed on the basis of the results of control experiments and relevant literature reviews.

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