Vinylcyclopropane-Cyclopentene (VCP-CP) Rearrangement Enabled by Pyridine-Assisted Boronyl Radical Catalysis

Li, Ting; Wei, Lanfeng; Wang, Zhijun; Zhang, Xinyu; Yang, Jinbo; Wei, Yu; Li, Pengfei; Xu, Liang

doi:10.1021/acs.orglett.4c01724

Org. Lett.

2024

DOI: 10.1021/acs.orglett.4c01724

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Vinylcyclopropane-Cyclopentene (VCP-CP) Rearrangement Enabled by Pyridine-Assisted Boronyl Radical Catalysis

Ting Li,

Lanfeng Wei,

Zhijun Wang

et al.

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2024

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Cited by 3 publications

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Regio‐ and Diastereoselective Synthesis of Polysubstituted Piperidines Enabled by Boronyl Radical‐Catalyzed (4+2) Cycloaddition

Ding,

Wang,

Wang

et al. 2024

Angewandte Chemie

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Piperidines are widely present in small molecule drugs and natural products. Despite many methods have been developed for their synthesis, new approaches to polysubstituted piperidines are highly desirable. This work presents a radical (4+2) cycloaddition reaction for synthesis of piperidines featuring dense substituents at 3,4,5‐positions that are not readily accessible by known methods. Using commercially available diboron(4) compounds and 4‐phenylpyridine as the catalyst precursors, the boronyl radical‐catalyzed cycloaddition between 3‐aroyl azetidines and various alkenes, including previously unreactive 1,2‐di‐, tri‐, and tetrasubstituted alkenes, has delivered the polysubstituted piperidines in generally high yield and diastereoselectivity. The reaction also features high modularity, atom economy, broad substrate scope, metal‐free conditions, simple catalysts and operation. The utilization of the products has been demonstrated by selective transformations. A plausible mechanism, with the ring‐opening of azetidine as the rate‐limiting step, has been proposed based on the experimental and computational results.

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Regio‐ and Diastereoselective Synthesis of Polysubstituted Piperidines Enabled by Boronyl Radical‐Catalyzed (4+2) Cycloaddition

Ding,

Wang,

Wang

et al. 2024

Angewandte Chemie

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Regio‐ and Diastereoselective Synthesis of Polysubstituted Piperidines Enabled by Boronyl Radical‐Catalyzed (4+2) Cycloaddition

Ding,

Wang,

Wang

et al. 2024

Angew Chem Int Ed

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Broad-Scope (3 + 2) Cycloaddition of Cyclopropanes and Alkynes Enabled by Boronyl Radical Catalysis

Wen,

Ding,

2024

Org. Lett.

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Cyclopentene skeletons are ubiquitous in natural products and small molecule drugs. The (3 + 2) cycloaddition of cyclopropanes and alkynes represents an efficient and atom-economic strategy for synthesizing these structures. However, the types of substituents on cyclopropane and alkyne used in previous works show evident limitations, restricting the application of this type of reaction to some extent. Herein, we report a broad-scope (3 + 2) cycloaddition of cyclopropanes and alkynes catalyzed by boronyl radicals. In this method, various substrates, such as mono-, di-, tri-, and tetrasubstituted cyclopropanes, as well as mono- and disubstituted alkynes, were compatible with up to 98% isolated yield.

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Vinylcyclopropane-Cyclopentene (VCP-CP) Rearrangement Enabled by Pyridine-Assisted Boronyl Radical Catalysis

Cited by 3 publications

References 38 publications

Regio‐ and Diastereoselective Synthesis of Polysubstituted Piperidines Enabled by Boronyl Radical‐Catalyzed (4+2) Cycloaddition

Regio‐ and Diastereoselective Synthesis of Polysubstituted Piperidines Enabled by Boronyl Radical‐Catalyzed (4+2) Cycloaddition

Regio‐ and Diastereoselective Synthesis of Polysubstituted Piperidines Enabled by Boronyl Radical‐Catalyzed (4+2) Cycloaddition

Broad-Scope (3 + 2) Cycloaddition of Cyclopropanes and Alkynes Enabled by Boronyl Radical Catalysis

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