Aromatization-Driven C–C Bond Cleavage of Unstrained Ketone Access to Vinyl Sulfones

Ketones, as simple and readily available bulk chemicals, have long been the focus of synthetic chemistry. Herein, we report a new protocol for the radical deconstruction of unstrained ketones by <i>in situ</i> conversion of them into dihydroquinoline (DHQ) prearomatics and subsequent oxidative aromatization. By combination with subsequent radical cascade reactions of DABSO and aryl acetylene, this protocol can convert acyclic and cyclic ketones and even ketone-containing complex natural products into a series of valuable vinyl sulfones in a one-pot, two-step method.

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Publication Details

Journal
Organic Letters
Published
2025-12-11
DOI
https://doi.org/10.1021/acs.orglett.5c04417
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
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article

Aromatization-Driven C–C Bond Cleavage of Unstrained Ketone Access to Vinyl Sulfones

Hongchen Wang, Yifan Li, Hong Fu, Pengfei Zhao et al.
Organic Letters
Sulfur-Based Synthesis Techniques
article

Aromatization-Driven C–C Bond Cleavage of Unstrained Ketone Access to Vinyl Sulfones

Hongchen Wang, Yifan Li, Hong Fu, Pengfei Zhao, Bing Han
article en

Abstract

Ketones, as simple and readily available bulk chemicals, have long been the focus of synthetic chemistry. Herein, we report a new protocol for the radical deconstruction of unstrained ketones by <i>in situ</i> conversion of them into dihydroquinoline (DHQ) prearomatics and subsequent oxidative aromatization. By combination with subsequent radical cascade reactions of DABSO and aryl acetylene, this protocol can convert acyclic and cyclic ketones and even ketone-containing complex natural products into a series of valuable vinyl sulfones in a one-pot, two-step method.

Organic LettersVol. 27(51)
State Key Laboratory of Chemical Engineering (CN), Lanzhou University (CN)
Openalex Percentile: Top 70%
Sulfur-Based Synthesis Techniques
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