52372-88-0Relevant academic research and scientific papers
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
supporting information, p. 1128 - 1133 (2017/08/18)
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.
Metal-Free Visible-Light-Mediated Oxidative Cross-Coupling of Thiols with P(O)H Compounds Using Air as the Oxidant
Sun, Jian-Guo,Yang, Hua,Li, Ping,Zhang, Bo
supporting information, p. 5114 - 5117 (2016/10/14)
Visible light along with 5 mol % of rose bengal catalyzes the direct S-P(O) coupling between thiols and P(O)H compounds in the presence of air as the green oxidant. The protocol is operationally simple and amenable to gram-scale synthesis. A variety of S-
TBPB-promoted metal-free synthesis of thiophosphinate/phosphonothioate by direct P-S bond coupling
Wang, Jichao,Huang, Xin,Ni, Zhangqin,Wang, Sichang,Wu, Jun,Pan, Yuanjiang
, p. 314 - 319 (2018/04/16)
An efficient method for the direct coupling of thiol/thiophenol with H-phosphine oxides or H-phosphinate esters is reported. Without using any metallic catalyst, the direct sulfur-phosphorus bond coupling reaction was promoted using tert-butyl peroxybenzo
Pseudohalogenation of phosphites
Shi, Enxue,Pei, Chengxin
, p. 2995 - 2998 (2007/10/03)
A new type of Atherton-Todd reaction for a convenient pseudohalogenation of phosphites has been developed. Direct azidation, cyanation, and thiocyanation of (RO)2P(O)H (R = Et, i-Bu, Ph) were accomplished readily with sodium pseudohalides in acetonitrile under mild modified Atherton-Todd conditions. The corresponding phosphorochloridates were demonstrated by GC/MS to be the intermediates. Pseudohalogenations of ethyl phenylphosphinate and diphenylphosphine oxide were also investigated.
Intramolecular nucleophilic displacement of halogen by phosphinate and thiophosphinate anions: Relative rates of formation of five- And six-membered rings 1
Chaudhry, Amirah,Hargcr, Martin J. P.,Shuff, Philippa,Thompson, Alison
, p. 1347 - 1352 (2007/10/03)
Intramolecular nucleophilic substitution transforms the phosphinate anions XCH2CH2(CH2)nCH2(Ph)P(O)O (n = 0, 1; X = Br, Cl) (Et3NH+ salts; CH2Cl2 solution) into cyclic phosphinate esters 14 (n - 0,1); unusually the five-membered ring product (n = 0) is formed only 4.3 (X = Br) or 5.7 (X = Cl) times faster than the six (n = 1). The analogous cyclisation of the thiophosphinate anions ClCH2CH2(CH2)nCH 2(Ph)P(S)CT (n = 0,1) gives the products 16 (n = 0, 1) with the sulfur atom in the ring; the five-membered ring is now formed 30 times faster than the six, still a rather modest rate advantage.
