21081-96-9Relevant articles and documents
Dimethyl sulfoxide as a mild oxidant in S-P(O) bond construction: Simple and metal-free approaches to phosphinothioates
Sun, Jian-Guo,Weng, Wei-Zhi,Li, Ping,Zhang, Bo
, p. 1128 - 1133 (2017)
In the presence of dimethyl sulfoxide (DMSO) as a mild oxidant and reaction medium, a simple and efficient protocol has been developed for the preparation of phosphinothioates via oxidative dehydrogenative phosphorylation of thiols with P(O)H compounds. Additionally, a DMSO-mediated oxidative phosphorylation of disulfides is also demonstrated. Notably, these transformations occur efficiently without the help of any transition metal or additive. These reactions are easy to conduct and can be scaled-up, and various phosphinothioates are readily obtained in moderate to excellent yields with excellent chemoselectivity and good functional-group tolerance.
An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides
Cheng, Feixiang,Liu, Jianjun,Liu, Teng,Yu, Rong,Zhang, Yanqiong
, p. 253 - 262 (2019/12/28)
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.
A scalable electrochemical dehydrogenative cross-coupling of P(O)H compounds with RSH/ROH
Li, Yujun,Yang, Qi,Yang, Liquan,Lei, Ning,Zheng, Ke
supporting information, p. 4981 - 4984 (2019/05/21)
A practical, scalable electrochemical dehydrogenative cross-coupling of P(O)H compounds with thiols, phenols and alcohols in both an undivided cell and a continuous-flow setup is disclosed. Its broad substrate scope (>50 examples), good functional-group tolerance and scalability (>10 g) show potential for practical synthesis. A preliminary mechanistic study suggests that the phosphorus radicals are involved in the catalytic cycle.
