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Rh(II)-Catalyzed Ring Expansion of Cyclopropyl N-Tosylhydrazones to 1-Substituted Cyclobutenes

Wenbai Ouyang, Jingfeng Huo*, Jianbo Wang*

*Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. of China, Email: jingfenghuouchicago.edu, wangjbpku.edu.cn

W. Ouyang, J. Huo, J. Wang, Synlett, 2023, 34, 1507-1511.

DOI: 10.1055/a-1995-5960


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Abstract

Cyclobutenes are highly useful synthetic intermediates as well as important motifs in functional molecules. A Rh-catalyzed ring expansion of cyclopropyl N-tosylhydrazone enables a straightforward synthesis of monosubstituted cyclobutenes. 1,2-Aryl or -alkyl shift of the Rh(II) carbene intermediate plays the key role in this transformation.

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Key Words

Rh(II) catalysis, N-tosylhydrazones, 1,2-shift, metal carbenes, cyclobutenes, cyclopropanes


ID: J72-Y2023