Regioselective Divergent Benzannulations of Vinyl Sulfoxonium Ylides with Electron-Deficient Alkynes

Herein, we report a regioselective [4 + 2] benzannulation strategy for the efficient synthesis of <i>m</i>-terphenyls and naphthalenes from vinyl sulfoxonium ylides, thiophenols, and electron-deficient alkynes. The selectivity of the benzannulation is governed by the nature of the ylide's stabilizing group. This modular approach features a broad substrate scope and enables streamlined access to highly substituted arenes with significant synthetic versatility.

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Publication Details

Journal
Organic Letters
Published
2025-09-03
DOI
https://doi.org/10.1021/acs.orglett.5c03066
Citations
1
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.94

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article

Regioselective Divergent Benzannulations of Vinyl Sulfoxonium Ylides with Electron-Deficient Alkynes

Daksh Singh Davas, Janakiram Vaitla, Raghunath Polai
1 citations
Organic Letters
Cyclopropane Reaction Mechanisms
0.94
article

Regioselective Divergent Benzannulations of Vinyl Sulfoxonium Ylides with Electron-Deficient Alkynes

Daksh Singh Davas, Janakiram Vaitla, Raghunath Polai
article en
1 citations

Abstract

Herein, we report a regioselective [4 + 2] benzannulation strategy for the efficient synthesis of <i>m</i>-terphenyls and naphthalenes from vinyl sulfoxonium ylides, thiophenols, and electron-deficient alkynes. The selectivity of the benzannulation is governed by the nature of the ylide's stabilizing group. This modular approach features a broad substrate scope and enables streamlined access to highly substituted arenes with significant synthetic versatility.

Organic LettersVol. 27(36)
Indian Institute of Technology Delhi (IN)
Council of Scientific and Industrial Research, India, Ministry of Education, India, Science and Engineering Research Board
Openalex Percentile: Top 22%
Cyclopropane Reaction Mechanisms
0.94
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