Chemoselective Synthesis of Unsymmetrical Dithioacetals through Sequential Carbene Insertion and Acetal Exchange of Acylsilanes and Thiols under Visible Light Irradiation

Dithioacetals are a frequently used motif in synthetic organic chemistry, and most existing reports discuss only symmetrical dithioacetals. Examples of unsymmetrical dithioacetals are scarce, and few general methods for the selective synthesis of these compounds exists. An intriguing visible-light-i...

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Bibliographic Details
Published in:Organic letters 2024-02, Vol.26 (6), p.1282-1286
Main Authors: Zhang, Wang, Yang, Dan-Ni, Guo, Dou-Dou, Wang, Peng, Han, Man-Yi
Format: Article
Language:English
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Summary:Dithioacetals are a frequently used motif in synthetic organic chemistry, and most existing reports discuss only symmetrical dithioacetals. Examples of unsymmetrical dithioacetals are scarce, and few general methods for the selective synthesis of these compounds exists. An intriguing visible-light-induced strategy has been established in this work for sequential reactions of S–H insertion and acetal exchange between acylsilanes and two different thiols that deliver a wide variety of unsymmetrical dithioacetals in moderate yields. The unsymmetrical dithioacetals were obtained with high selectivity, and a great variety of functional groups were tolerated.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00133