Copper-catalyzed carbo-difluoromethylation of alkenes via radical relay

Aijie Cai, Wenhao Yan, Xiaojun Zeng, Samson B. Zacate, Tzu Hsuan Chao, Jeanette A. Krause, Mu Jeng Cheng, Wei Liu

研究成果: Article同行評審

1 引文 斯高帕斯(Scopus)

摘要

Organic molecules that contain alkyl-difluoromethyl moieties have received increased attention in medicinal chemistry, but their synthesis in a modular and late-stage fashion remains challenging. We report herein an efficient copper-catalyzed radical relay approach for the carbo-difluoromethylation of alkenes. This approach simultaneously introduces CF2H groups along with complex alkyl or aryl groups into alkenes with regioselectivity opposite to traditional CF2H radical addition. We demonstrate a broad substrate scope and a wide functional group compatibility. This scalable protocol is applied to the late-stage functionalization of complex molecules and the synthesis of CF2H analogues of bioactive molecules. Mechanistic studies and density functional theory calculations suggest a unique ligand effect on the reactivity of the Cu-CF2H species.

原文English
文章編號3272
期刊Nature communications
12
發行號1
DOIs
出版狀態Published - 2021 十二月

All Science Journal Classification (ASJC) codes

  • 化學 (全部)
  • 生物化學、遺傳與分子生物學 (全部)
  • 物理與天文學 (全部)

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