Photoinduced Pd‐Catalyzed Direct Sulfonylation of Allylic C−H Bonds

Allylic sulfones are valuable motifs due to their medicinal and biological significance and their versatile chemical reactivities. While direct allylic C-H sulfonylation represents a straightforward and desirable approach, these methods are primarily restricted to terminal alkenes, leaving the engagement of the internal counterparts a formidable challenge. Herein we report a photocatalytic approach that accommodates both cyclic and acyclic internal alkenes with diverse substitution patterns and electronic properties. Importantly, the obtained allylic sulfones can be readily diversified into a wide range of products, thus enabling formal alkene transposition and all-carbon quaternary center formation through the sequential C-H functionalization.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2024-09-17
DOI
https://doi.org/10.1002/anie.202413646
Citations
29
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
7.25

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article

Photoinduced Pd‐Catalyzed Direct Sulfonylation of Allylic C−H Bonds

Kelvin Pak Shing Cheung, Vladimir Gevorgyan, Kallol Mukherjee
29 citations
Angewandte Chemie International Edition
Sulfur-Based Synthesis Techniques
7.25
article

Photoinduced Pd‐Catalyzed Direct Sulfonylation of Allylic C−H Bonds

Kelvin Pak Shing Cheung, Vladimir Gevorgyan, Kallol Mukherjee
article en
29 citations

Abstract

Allylic sulfones are valuable motifs due to their medicinal and biological significance and their versatile chemical reactivities. While direct allylic C-H sulfonylation represents a straightforward and desirable approach, these methods are primarily restricted to terminal alkenes, leaving the engagement of the internal counterparts a formidable challenge. Herein we report a photocatalytic approach that accommodates both cyclic and acyclic internal alkenes with diverse substitution patterns and electronic properties. Importantly, the obtained allylic sulfones can be readily diversified into a wide range of products, thus enabling formal alkene transposition and all-carbon quaternary center formation through the sequential C-H functionalization.

Angewandte Chemie International EditionVol. 64(1)
The University of Texas at Dallas (US)
Welch Foundation, University of Texas at San Antonio, National Institutes of Health, National Institute of General Medical Sciences, Division of Chemistry
Clean water and sanitation
Openalex Percentile: Top 2%
Sulfur-Based Synthesis Techniques
7.25
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