Iridium-catalyzed [3+2] cyclization of terminal alkynes with sulfoxonium ylides to construct 2,5-disubstituted furans

A novel iridium-catalyzed [3+2] cyclization of sulfoxonium ylides with terminal alkynes for the synthesis of 2,5-disubstituted furans has been demonstrated. This protocol features a broad substrate scope, mild reaction conditions, and good to excellent yields. Mechanistic studies indicate that the reaction may involve the C(sp)-H bond insertion of sulfoxide ylides to generate allenones, followed by cyclization. In addition, late-stage functionalization of complex architectures shows the utility of this method.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc05655a
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.94
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article

Iridium-catalyzed [3+2] cyclization of terminal alkynes with sulfoxonium ylides to construct 2,5-disubstituted furans

Wei Xu, Xiaobao Zeng, Hai‐Chao Han, Biao Xiong et al.
1 citations
Chemical Communications
Catalytic C–H Functionalization Methods
0.94
article

Iridium-catalyzed [3+2] cyclization of terminal alkynes with sulfoxonium ylides to construct 2,5-disubstituted furans

Wei Xu, Xiaobao Zeng, Hai‐Chao Han, Biao Xiong, Zhou Li, Yi Song, DongXiang Yan
article en
1 citations

Abstract

A novel iridium-catalyzed [3+2] cyclization of sulfoxonium ylides with terminal alkynes for the synthesis of 2,5-disubstituted furans has been demonstrated. This protocol features a broad substrate scope, mild reaction conditions, and good to excellent yields. Mechanistic studies indicate that the reaction may involve the C(sp)-H bond insertion of sulfoxide ylides to generate allenones, followed by cyclization. In addition, late-stage functionalization of complex architectures shows the utility of this method.

Chemical CommunicationsVol. 61(93)
Nantong University (CN)
Openalex Percentile: Top 20%
Catalytic C–H Functionalization Methods
0.94
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