Microwave-assisted copper catalysis of α-difluorinated gem-diol toward difluoroalkyl radical for hydrodifluoroalkylation of para-quinone methides

Hong Yu Li, Zhi Gang Xu, Zhong Zhu Chen, Chuan Hua Qu, Gui Ting Song, Dian Yong Tang, Jing Wei Shao

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Reported herein is a unified strategy to generate difluoroalkyl radicals from readily prepared α-difluorinated gemdiols by single electron oxidation. Under microwave irradiation, a catalytic amount of oxidant Cu(OAc)2 succeeds in the formation of transient difluoroalkyl radicals in situ, for the first time. The reaction features a simple protocol, short reaction time, scalability, and high yield. The synthetic utility of this new methodology was also explored for the synthesis of difluoroalkylated spiro-cyclohexadienones, which is an important core structure in natural products and pharmaceuticals.

Original languageEnglish (US)
Pages (from-to)12785-12796
Number of pages12
JournalJournal of Organic Chemistry
Volume85
Issue number19
DOIs
StatePublished - Oct 2 2020
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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