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DOI: 10.1055/s-0041-1738430
Synthesis of N-Acylsulfenamides from Amides and N-Thiosuccinimides
This work was supported by NIH Grant R35GM122473 (to J.A.E.). J.T.L. was funded by the Yale College First-Year Summer Research Fellowship in the Sciences and Engineering. D.S.B. acknowledges the Berson Graduate Research Fellowship in Chemistry for financial support. N.S.G. gratefully acknowledges the support of the National Science Foundation Graduate Research Fellowship Program.
This work is dedicated to the memory of David A. Evans for his commitment and lasting contributions to research and teaching.
Abstract
Herein is reported a robust and general method for the preparation of N-acylsulfenamides, important functionalities that have recently been utilized as central inputs for the asymmetric synthesis of high oxidation state sulfur compounds. This straightforward transformation proceeds by reaction of primary amides, carbamates, sulfonamides, sulfinamides, and ureas with stable N-thiosuccinimides or N-thiophthalimides, which in turn are prepared in a single step from commercial thiols. The use of stable N-thiosuccinimide and N-thiophthalimide reactants is desirable because it obviates the use of highly reactive sulfenyl chlorides.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738430.
- Supporting Information
Publication History
Received: 26 October 2022
Accepted after revision: 22 November 2022
Article published online:
20 December 2022
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