Deuterium- and Electron-Shuttling Catalysis for Deoxygenative Deuteration of Alcohols

A practical and precise method for visible-light-promoted deoxygenative deuteration of common aliphatic alcohols using D2O as the deuterium source is reported. Upon intermediacy of xanthate anions, a variety of primary, secondary, and tertiary alcohols can be facilely transformed into deuterioalkane...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 35; pp. 6571 - 6576
Main Authors He, Bin-Qing, Wu, Xuesong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 08.09.2023
Amer Chemical Soc
Subjects
catalysts
catalytic activity
Chemistry
Chemistry, Organic
deuterium
Physical Sciences
Science & Technology
D2O
ALIPHATIC-ALCOHOLS
ACTIVATION
REDUCTION
ALLYLIC ALCOHOLS
PHOTOCATALYTIC TRANSFER HYDROGENOLYSIS
ATOM TRANSFER
DISULFIDES
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Summary:A practical and precise method for visible-light-promoted deoxygenative deuteration of common aliphatic alcohols using D2O as the deuterium source is reported. Upon intermediacy of xanthate anions, a variety of primary, secondary, and tertiary alcohols can be facilely transformed into deuterioalkanes with excellent D-incorporation at predicted sites. The deoxygenation and deuteration sequence is catalyzed by in situ formed deuterated 2-mercaptopyridine, which plays dual roles as a deuterium atom transfer catalyst and an electron shuttle as well.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c02432