1451371-44-0Relevant academic research and scientific papers
Stereoretentive C(sp3)-S Cross-Coupling
Zhu, Feng,Miller, Eric,Zhang, Shuo-Qing,Yi, Duk,O'Neill, Sloane,Hong, Xin,Walczak, Maciej A.
, p. 18140 - 18150 (2019/01/04)
We report a stereoretentive cross-coupling reaction of configurationally stable nucleophiles with disulfide and N-sulfenylsuccinimide donors promoted by Cu(I). We demonstrate the utility of this method in the synthesis of thioglycosides derived from simple alkyl and aryl thiols, thioglycosides, and in the glycodiversification of cysteine residues in peptides. These reactions operate well with carbohydrate substrates containing common protective groups and reagents with free hydroxyl and secondary amide functionalities under standardized conditions. Competition experiments in combination with computational DFT studies established that the putative anomeric intermediate is an organocopper species that is configurationally stable and resistant to epimerization due to its short lifetime. The subsequent reductive elimination from the Cu(III) intermediate is rapid and stereoretentive. Taken together, the glycosyl cross-coupling is ideally suited for late stage glycodiversification and bioconjugation under highly controlled installation of the aliphatic carbon-sulfur bonds.
Visible-Light-Induced Direct Thiolation at α-C(sp3)-H of Ethers with Disulfides Using Acridine Red as Photocatalyst
Zhu, Xianjin,Xie, Xiaoyu,Li, Pinhua,Guo, Jianqi,Wang, Lei
supporting information, p. 1546 - 1549 (2016/05/02)
A simple and efficient method for the preparation of α-arylthioethers through a visible-light-induced direct thiolation at α-C(sp3)-H of ethers with diaryl disulfides was developed using acridine red as a novel photocatalyst. The reactions occurred at ambient conditions and generated the corresponding products in good to excellent yields, ignoring steric effect of disulfides.
Metal-free oxidative C(sp3)-H bond thiolation of ethers with disulfides
Guo, Sheng-Rong,Yuan, Yan-Qin,Xiang, Jian-Nan
supporting information, p. 4654 - 4657 (2013/10/08)
A novel method for the preparation of alkyl aryl sulfides through direct oxidation thiolation of commercial ethers with diaryl disulfides using di-tert-butyl peroxide (DTBP) as the oxidant without a metal catalyst was established. The C(sp3)-H
