7417-73-4Relevant articles and documents
Zirconium-catalysed direct substitution of alcohols: enhancing the selectivity by kinetic analysis
Camaj, David,Carlsson, Robin,Dalla-Santa, Oscar,Lill, Malin,Lundberg, Helena,Margarita, Cristiana,Ramstr?m, Anja,Tu?on, Hernando,Villo, Piret
, p. 7420 - 7430 (2021/11/23)
Kinetic analysis was used as a tool for rational optimization of a catalytic, direct substitution of alcohols to enable the selective formation of unsymmetrical ethers, thioethers, and Friedel-Crafts alkylation products using a moisture-tolerant and commercially available zirconium complex (2 to 8 mol%). Operating in air and in the absence of dehydration techniques, the protocol furnished a variety of products in high yields, including glycosylated alcohols and sterically hindered ethers. In addition, the kinetic studies provided mechanistic insight into the network of parallel transformations that take place in the reaction, and helped to elucidate the nature of the operating catalyst.
Indium-Catalyzed Reductive Sulfidation of Esters by Using Thiols: An Approach to the Diverse Synthesis of Sulfides
Miyazaki, Takahiro,Kasai, Shinsei,Ogiwara, Yohei,Sakai, Norio
, p. 1043 - 1049 (2016/03/01)
A new reductive preparation of unsymmetrical sulfides from esters and thiols in the presence of InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 as the reductant was developed. This protocol was applied to not only benzoic acid esters that have a methoxy, methyl, chloro, bromo, iodo, or trifluoromethyl group on the aromatic ring but also aliphatic acid esters with either aromatic or aliphatic thiols. A reaction mechanism is proposed by using Hammett plot results and several control experiments. The reductive preparation of unsymmetrical sulfides from esters and thiols by using InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 was developed. Several mechanistic studies support that the present transformation proceeds through O,S-and S,S-acetals as the reaction intermediates. TMDS = 1,1,3,3-tetramethyldisiloxane, R = aliphatic group.
Enantioselective synthesis of benzyl tert-butyl sulfoxides
Syed, Majid Khalil,Casey, Mike
experimental part, p. 7207 - 7214 (2012/01/16)
Enantiomerically pure benzyl sulfoxides are effective tools for the formation of new C-C bonds with control of configuration at new stereogenic centres. The reaction of enantioenriched tert-butyl tert-butanethiosulfinate with benzyllithium derivatives, ob