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Synthesis 2021; 53(20): 3769-3776
DOI: 10.1055/a-1516-8481
DOI: 10.1055/a-1516-8481
paper
Copper-Catalyzed Sulfonylation of Cyclobutanone Oxime Esters with Sulfonyl Hydrazides
This 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).
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 catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1516-8481.
- Supporting Information
Primary Data
Primary data for this article are available online at https://doi.org/10.5281/zenodo.5044624 and can be cited using the following DOI: 10.5281/zenodo.5044624.
Publikationsverlauf
Eingereicht: 27. April 2021
Angenommen nach Revision: 25. Mai 2021
Accepted Manuscript online:
25. Mai 2021
Artikel online veröffentlicht:
01. Juli 2021
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