Selective deoxygenative alkylation of alcohols via photocatalytic domino radical fragmentations

作者：Hongmei Guo, Xuesong Wu · 发表于：Nature Communications · 年份：2021 · DOI：10.1038/s41467-021-25702-4 · 被引用次数：127 · 研究领域：Radical Photochemical Reactions、Sulfur-Based Synthesis Techniques、Catalytic C–H Functionalization Methods

The delivery of alkyl radicals through photocatalytic deoxygenation of primary alcohols under mild conditions is a so far unmet challenge. In this report, we present a one-pot strategy for deoxygenative Giese reaction of alcohols with electron-deficient alkenes, by using xanthate salts as alcohol-activating groups for radical generation under visible-light photoredox conditions in the presence of triphenylphosphine. The convenient generation of xanthate salts and high reactivity of sequential C-S/C-O bond homolytic cleavage enable efficient deoxygenation of primary, secondary and tertiary alcohols with diverse functionality and structure to generate the corresponding alkyl radicals, including methyl radical. Moreover, chemoselective radical monodeoxygenation of diols is achieved via selective formation of xanthate salts.