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Synthesis 2020; 52(02): 253-262
DOI: 10.1055/s-0039-1690709
DOI: 10.1055/s-0039-1690709
paper
An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides
This work was supported by the Program for the Application of Fundamental Research of Yunnan Province (Grant No. 2018FB019), the Opening Foundation of the Key Laboratory of Natural Resources and Pharmaceutical Chemistry, Ministry of Education, Yunnan University, and the National Natural Science Foundation of China (Grant No. 21961030).Further Information
Publication History
Received: 06 August 2019
Accepted after revision: 20 September 2019
Publication Date:
17 October 2019 (online)
Abstract
An alternative metal-free, efficient and practical approach for the preparation of phosphinothioates is established via the aerobic oxidative cross-dehydrogenative coupling (CDC) of sulfonyl hydrazides with secondary phosphine oxides catalyzed by tetrabutylammonium iodide (TBAI) in the presence of atmospheric oxygen. The strategy provides an array of diverse phosphinothioates in good to excellent yields. Furthermore, two representative bioactive molecules are synthesized on up to gram scale by utilizing this method.
Key words
phosphinothioates - metal-free - cross-dehydrogenative coupling - secondary phosphine oxides - sulfonyl hydrazidesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690709.
- Supporting Information
- CIF File
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