Ag-Mediated Sulfonyl-Alkenylationof Unactivated Alkynesvia Intramolecular C(sp2)-H Cyclization toward 1,2-Dihydropyridines

Abstract 1,2-Dihydropyridines and sulfonyl compounds are widely found in bioactive molecules and functional materials. Herein, a silver-mediated radical sulfonyl-alkenylation of vinylamino-linked alkynes with sodium sulfinates via intramolecular C(sp2)-H cyclization for producing sulfonylated 1,2-dihydropyridines in a highly selective manner was developed. The two-component alkyne sulfonyl-alkenylation enables the construction of two new bonds, including a C(sp2)-S bond and a C(sp2)-C(sp2) bond, through the sulfonyl radical formation, selective radical across the alkyne moiety and alkenylation cascades, and represents an efficient route to preparing a series of sulfonylated 1,2-dihydropyridines with up to 98% yields with high regioselectivities and good functional group tolerance.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-08-18
DOI
https://doi.org/10.1021/acs.joc.6c01543
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Ag-Mediated Sulfonyl-Alkenylationof Unactivated Alkynesvia Intramolecular C(sp2)-H Cyclization toward 1,2-Dihydropyridines

Peng‐Fei Huang, Jin‐Heng Li, Long‐Jin Zhong, Yu Liu et al.
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

Ag-Mediated Sulfonyl-Alkenylationof Unactivated Alkynesvia Intramolecular C(sp2)-H Cyclization toward 1,2-Dihydropyridines

Peng‐Fei Huang, Jin‐Heng Li, Long‐Jin Zhong, Yu Liu, Mei-Jin Gao
article en

Abstract

Abstract 1,2-Dihydropyridines and sulfonyl compounds are widely found in bioactive molecules and functional materials. Herein, a silver-mediated radical sulfonyl-alkenylation of vinylamino-linked alkynes with sodium sulfinates via intramolecular C(sp2)-H cyclization for producing sulfonylated 1,2-dihydropyridines in a highly selective manner was developed. The two-component alkyne sulfonyl-alkenylation enables the construction of two new bonds, including a C(sp2)-S bond and a C(sp2)-C(sp2) bond, through the sulfonyl radical formation, selective radical across the alkyne moiety and alkenylation cascades, and represents an efficient route to preparing a series of sulfonylated 1,2-dihydropyridines with up to 98% yields with high regioselectivities and good functional group tolerance.

The Journal of Organic Chemistry
Hunan Institute of Science and Technology (CN), Qingdao University of Science and Technology (CN)
Clean water and sanitation
Openalex Percentile: Top 18%
Sulfur-Based Synthesis Techniques
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Ag-Mediated Sulfonyl-Alkenylationof Unactivated Alkynesvia Intramolecular C(sp2)-H Cyclization toward 1,2-Dihydropyridines — Peng‐Fei Huang, Jin‐Heng Li, et al. · The Journal of Organic Chemistry (2026) | TGRS Research Map | TGRS