Synthesis 2020; 52(05): 695-702
DOI: 10.1055/s-0039-1691505
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Sulfonylisoureas via Sulfo-Click Reactions

Moritz Ottenbruch
,
Fabian Mohr
,
Bergische Universität Wuppertal, Gaußstr. 20, 42119 Wuppertal, Germany   Email: sfkirsch@uni-wuppertal.de
› Author Affiliations
Further Information

Publication History

Received: 04 November 2019

Accepted after revision: 10 November 2019

Publication Date:
27 November 2019 (online)


Abstract

The synthesis of sulfonylisoureas from thiocarbamates and sulfonyl azides via a new variant of the sulfo-click reaction is reported. Water was found to be the environmentally benign solvent of choice over various other solvents tested, and the use of any additives was not required to obtain complete conversion. The experimentally simple reaction­ tolerates a broad range of electron-donating and electron-withdrawing substituents attached on both the thiocarbamate and the sulfonyl azide, as shown with the synthesis of 27 sulfonylisoureas that were prepared in yields ranging from 34% to 78%.

Supporting Information