Journal
ORGANIC LETTERS
Volume 24, Issue 40, Pages 7361-7365Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02895
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Funding
- JSPS KAKENHI [JP17H01523, JP19K15711]
- Research Support Project for Life Science and Drug Discovery (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from the Japan Agency for Medical Research and Development (AMED) [JP22ama121044]
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Treatment of alpha-azido sulfones with a thiol in the presence of 1,1,3,3-tetramethylguanidine leads to the formation of alpha-azido sulfides through sulfonyl group substitution. Experimental and DFT calculations suggest a reaction mechanism involving thiolate addition to the azido group and generation of an alkylidene triazene.
Upon treatment of alpha-azido sulfones with a thiol in the presence of 1,1,3,3-tetramethylguanidine, substitution of the sulfonyl group with a thiolate occurred, resulting in the formation of alpha-azido sulfides. Based on experimental results and DFT calculations, a reaction mechanism that involves the addition of a thiolate to the azido group and generation of an alkylidene triazene is proposed.
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