Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols

Sulfenamides are organosulfur reagents that feature labile S–N bonds and have potential applications in chemical synthesis. Here, the authors report the preparation of N-acyl sulfenamides via copper-catalyzed S-amidation of thiols with dioxazolones; These N-acyl sulfenamides can be used to prepare u...

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Main Authors: Ziqian Bai, Shiyang Zhu, Yiyao Hu, Peng Yang, Xin Chu, Gang He, Hao Wang, Gong Chen
Format: Article
Language:English
Published: Nature Portfolio 2022-10-01
Series:Nature Communications
Online Access:https://doi.org/10.1038/s41467-022-34223-7
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author Ziqian Bai
Shiyang Zhu
Yiyao Hu
Peng Yang
Xin Chu
Gang He
Hao Wang
Gong Chen
author_facet Ziqian Bai
Shiyang Zhu
Yiyao Hu
Peng Yang
Xin Chu
Gang He
Hao Wang
Gong Chen
author_sort Ziqian Bai
collection DOAJ
description Sulfenamides are organosulfur reagents that feature labile S–N bonds and have potential applications in chemical synthesis. Here, the authors report the preparation of N-acyl sulfenamides via copper-catalyzed S-amidation of thiols with dioxazolones; These N-acyl sulfenamides can be used to prepare unsymmetrical disulfides via reaction with thiols.
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spelling doaj.art-1ede04ff0a504508acfb0e315e4d99042022-12-22T02:37:58ZengNature PortfolioNature Communications2041-17232022-10-011311910.1038/s41467-022-34223-7Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiolsZiqian Bai0Shiyang Zhu1Yiyao Hu2Peng Yang3Xin Chu4Gang He5Hao Wang6Gong Chen7State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai UniversityState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai UniversityState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai UniversityState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai UniversityState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai UniversityState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai UniversityState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai UniversityState Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai UniversitySulfenamides are organosulfur reagents that feature labile S–N bonds and have potential applications in chemical synthesis. Here, the authors report the preparation of N-acyl sulfenamides via copper-catalyzed S-amidation of thiols with dioxazolones; These N-acyl sulfenamides can be used to prepare unsymmetrical disulfides via reaction with thiols.https://doi.org/10.1038/s41467-022-34223-7
spellingShingle Ziqian Bai
Shiyang Zhu
Yiyao Hu
Peng Yang
Xin Chu
Gang He
Hao Wang
Gong Chen
Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols
Nature Communications
title Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols
title_full Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols
title_fullStr Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols
title_full_unstemmed Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols
title_short Synthesis of N-acyl sulfenamides via copper catalysis and their use as S-sulfenylating reagents of thiols
title_sort synthesis of n acyl sulfenamides via copper catalysis and their use as s sulfenylating reagents of thiols
url https://doi.org/10.1038/s41467-022-34223-7
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