Direct Photoexcitation of Xanthate Anions for Deoxygenative Alkenylation of Alcohols

In this report, we identify xanthate salts as a unique class of visible-light-excitable alkyl radical precursors that act simultaneously as strong photoreductants and alkyl radical sources. Upon direct photoexcitation of xanthate anions, efficient deoxygenative alkenylation and alkylation of a wide...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 17; pp. 3199 - 3204
Main Authors Guo, Hong-Mei, He, Bin-Qing, Wu, Xuesong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.05.2022
Amer Chemical Soc
Subjects
alkylation
Chemistry
Chemistry, Organic
photocatalysts
photochemical reactions
Physical Sciences
Science & Technology
CATALYSIS
TERTIARY ALCOHOLS
VINYLATION
CONSTRUCTION
ARYLATION
QUATERNARY CARBONS
DESULFURIZATION
RADICAL GENERATION
PRECURSORS
OXALATES
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Summary:In this report, we identify xanthate salts as a unique class of visible-light-excitable alkyl radical precursors that act simultaneously as strong photoreductants and alkyl radical sources. Upon direct photoexcitation of xanthate anions, efficient deoxygenative alkenylation and alkylation of a wide range of primary, secondary, and tertiary alcohols have been achieved via a one-pot protocol, avoiding any photocatalysts. This method exhibits a broad substrate scope and good functional group tolerance, enabling late-stage functionalization of complex molecules.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.2c00889