Photocatalytic Redox-Neutral and Reductive Deoxygenative Alkylation of Benzyl Alcohols Using <i>N</i>-Acyl Carbamothioates as Radical Precursors

Herein, we report a photocatalytic redox-neutral and reductive deoxygenative alkylation of <i>N</i>-acyl carbamothioates from benzylic alcohols, with substituted Hantzsch esters and allylic sulfones to afford unsymmetrical 1,2-diaryl ethanes and allylarylmethanes, respectively. This protocol facilitates facile deoxyalkylation of primary, secondary, and tertiary benzylic alcohol-derived <i>N</i>-acyl carbamothioates, which features mild reaction conditions, broad functional group tolerance, and the obviation of external S/O trapping reagents as well as transition metal-coupling catalysts.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-02-26
DOI
https://doi.org/10.1021/acs.joc.4c02942
Citations
2
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.87

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article

Photocatalytic Redox-Neutral and Reductive Deoxygenative Alkylation of Benzyl Alcohols Using N-Acyl Carbamothioates as Radical Precursors

Min Chen, Junhao Li, Yuanxin Liu, Yaqun Liu et al.
2 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
1.87
article

Photocatalytic Redox-Neutral and Reductive Deoxygenative Alkylation of Benzyl Alcohols Using N-Acyl Carbamothioates as Radical Precursors

Min Chen, Junhao Li, Yuanxin Liu, Yaqun Liu, Li Wang
article en
2 citations

Abstract

Herein, we report a photocatalytic redox-neutral and reductive deoxygenative alkylation of <i>N</i>-acyl carbamothioates from benzylic alcohols, with substituted Hantzsch esters and allylic sulfones to afford unsymmetrical 1,2-diaryl ethanes and allylarylmethanes, respectively. This protocol facilitates facile deoxyalkylation of primary, secondary, and tertiary benzylic alcohol-derived <i>N</i>-acyl carbamothioates, which features mild reaction conditions, broad functional group tolerance, and the obviation of external S/O trapping reagents as well as transition metal-coupling catalysts.

The Journal of Organic ChemistryVol. 90(9)
Wuhan University of Technology (CN)
National Natural Science Foundation of China, Natural Science Foundation of Hubei Province, Wuhan University of Technology
Clean water and sanitation
Openalex Percentile: Top 17%
Radical Photochemical Reactions
1.87
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Photocatalytic Redox-Neutral and Reductive Deoxygenative Alkylation of Benzyl Alcohols Using <i>N</i>-Acyl Carbamothioates as Radical Precursors — Min Chen, Junhao Li, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS