In(OTf) <sub>3</sub> -Catalyzed [3 + 2] Cycloaddition Reactions of Donor–Acceptor Cyclopropanes with Thioamides

An In(OTf)<sub>3</sub>-catalyzed [3 + 2] cycloaddition reaction between donor-acceptor cyclopropanes enabled by a single keto acceptor (cyclopropyl ketones) and thioamides has been developed. The broad substrate scope has been demonstrated by synthesizing a series of new highly functionalized dihydrothiophenes with up to a 95% isolated yield. In addition, the protocol can be applied to the double [3 + 2] cycloaddition reactions of bicyclopropanes with thioamide.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-05
DOI
https://doi.org/10.1021/acs.joc.5c01959
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
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article

In(OTf) 3 -Catalyzed [3 + 2] Cycloaddition Reactions of Donor–Acceptor Cyclopropanes with Thioamides

Yue Lu, Yan Jiang, Wenzhi Zhao, Chen-Ying Zhai
The Journal of Organic Chemistry
Cyclopropane Reaction Mechanisms
article

In(OTf) 3 -Catalyzed [3 + 2] Cycloaddition Reactions of Donor–Acceptor Cyclopropanes with Thioamides

Yue Lu, Yan Jiang, Wenzhi Zhao, Chen-Ying Zhai
article en

Abstract

An In(OTf)<sub>3</sub>-catalyzed [3 + 2] cycloaddition reaction between donor-acceptor cyclopropanes enabled by a single keto acceptor (cyclopropyl ketones) and thioamides has been developed. The broad substrate scope has been demonstrated by synthesizing a series of new highly functionalized dihydrothiophenes with up to a 95% isolated yield. In addition, the protocol can be applied to the double [3 + 2] cycloaddition reactions of bicyclopropanes with thioamide.

The Journal of Organic ChemistryVol. 90(50)
China West Normal University (CN), Division of Materials Science and Engineering (AU), Green Chemistry (PL), Chemical Synthesis Lab (SG), Sichuan University of Science and Engineering (CN)
Openalex Percentile: Top 71%
Cyclopropane Reaction Mechanisms
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