Synthesis of donor-acceptor type 1,1-bis(sulfonyl)cyclopropanes from active bis(sulfonyl)methylene compounds using sulfonium salts

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-02-01 DOI:10.1016/j.tet.2025.134514

Kotaro Ezoe, Kosuke Murakami, Keisuke Tomohara, Hisanori Nambu

引用次数: 0

Abstract

An efficient synthesis of donor-acceptor type 1,1-bis(sulfonyl)cyclopropanes was achieved using sulfonium salts. The reaction of active bis(sulfonyl)methylene compounds with (1-aryl-2-bromoethyl)dimethylsulfonium bromides and potassium carbonate in aqueous ethyl acetate afforded the corresponding 2-aryl-1,1-bis(sulfonyl)cyclopropanes in good to excellent yields. Furthermore, the synthesis of 2,3-nonsubstituted 1,1-bis(sulfonyl)cyclopropanes from bis(sulfonyl)methanes was also achieved using (2-bromoethyl)diphenylsulfonium trifluoromethanesulfonate. The resulting 1,1-bis(sulfonyl)cyclopropanes are expected to serve as versatile small-molecule synthons.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.