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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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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Abstract 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.
AbstractList In this report, we identify xanthate salts as a unique class of visible-light-excitable alkyl radical precursorsthatactsimultaneouslyasstrongphotoreductants and alkyl radical sources. Upon direct photoexcitation ofxanthate anions, efficient deoxygenative alkenylation and alkylation of a widerange of primary, secondary, and tertiary alcohols have been achieved via a one-pot protocol, avoiding any photocatalysts. This method exhibits a broad substratescope and good functional group tolerance, enabling late-stage functionalizationof complex molecules.
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.
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.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.
Author Guo, Hong-Mei
Wu, Xuesong
He, Bin-Qing
AuthorAffiliation Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry and Chemical Engineering
AuthorAffiliation_xml – name: Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry and Chemical Engineering
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  givenname: Xuesong
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  surname: Wu
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  email: xswu@hust.edu.cn
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Issue 17
Keywords CATALYSIS
TERTIARY ALCOHOLS
VINYLATION
CONSTRUCTION
ARYLATION
QUATERNARY CARBONS
DESULFURIZATION
RADICAL GENERATION
PRECURSORS
OXALATES
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Snippet In this report, we identify xanthate salts as a unique class of visible-light-excitable alkyl radical precursors that act simultaneously as strong...
In this report, we identify xanthate salts as a unique class of visible-light-excitable alkyl radical precursorsthatactsimultaneouslyasstrongphotoreductants...
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SubjectTerms alkylation
Chemistry
Chemistry, Organic
photocatalysts
photochemical reactions
Physical Sciences
Science & Technology
Title Direct Photoexcitation of Xanthate Anions for Deoxygenative Alkenylation of Alcohols
URI http://dx.doi.org/10.1021/acs.orglett.2c00889
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https://www.ncbi.nlm.nih.gov/pubmed/35467887
https://www.proquest.com/docview/2655561266
https://www.proquest.com/docview/2675580429
Volume 24
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