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Synthesis 2021; 53(20): 3769-3776
DOI: 10.1055/a-1516-8481
paper

Copper-Catalyzed Sulfonylation of Cyclobutanone Oxime Esters with Sulfonyl Hydrazides

Bingbing Dong
a   Green Catalysis Center, and College of Chemistry; Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province; Zhengzhou University, No.100 Science Avenue, Zhengzhou 450001, P. R. of China
,
Jiansha Lu∗
a   Green Catalysis Center, and College of Chemistry; Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province; Zhengzhou University, No.100 Science Avenue, Zhengzhou 450001, P. R. of China
,
Honghao Bao
a   Green Catalysis Center, and College of Chemistry; Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province; Zhengzhou University, No.100 Science Avenue, Zhengzhou 450001, P. R. of China
,
Yuanyuan Zhang
a   Green Catalysis Center, and College of Chemistry; Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province; Zhengzhou University, No.100 Science Avenue, Zhengzhou 450001, P. R. of China
,
Yingguo Liu
b   Division of Molecular Catalysis & Synthesis, Henan Institute of Advanced Technology, Zhengzhou University, No.100 Science Avenue, Zhengzhou 450001, P. R. of China
,
Yuting Leng∗
a   Green Catalysis Center, and College of Chemistry; Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province; Zhengzhou University, No.100 Science Avenue, Zhengzhou 450001, P. R. of China
› Author AffiliationsThis work was supported by grants from the Top Youth Talent Fund of Zhengzhou University and The State Key Laboratory of Bio-organic and Natural Products Chemistry, Chinese Academy of Sciences (CAS) (SKLBNPC18440).
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Abstract

A copper-catalyzed radical cross-coupling of cyclobutanone oxime esters with sulfonyl hydrazides has been developed. The copper-based catalytic system proved crucial for cleavage of the C−C bond of cyclobutanone oximes and for selective C–S bond-formation involving persistent sulfonyl-metal radical intermediates. This protocol is distinguished by the low-cost catalytic system, which does not require ligand, base, or toxic cyanide salt, and by the use of readily accessible starting materials, as well as broad substrate scope, providing an efficient approach to various diversely substituted cyano-containing sulfones.

Key words

sulfonylation - radical cross-coupling - cyclobutanone oxime esters - sulfonyl hydrazides catalysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1516-8481.
  • Supporting Information

Primary Data



Publication History

Received: 27 April 2021

Accepted after revision: 25 May 2021

Accepted Manuscript online:
25 May 2021

Article published online:
01 July 2021

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