1269772-84-0Relevant academic research and scientific papers
Copper-Catalyzed Stereospecific C-S Coupling Reaction of Enantioenriched Tertiary Benzylic Amines via in Situ Activation with Methyl Triflate
Jiang, Wenlong,Li, Nutao,Zhou, Lihong,Zeng, Qingle
, p. 9899 - 9906 (2018/10/15)
A one-pot protocol for the synthesis of highly enantiopure benzylic thioethers, thioacetates, and sulfones (94-99% ee) via a ligand-free, copper-catalyzed stereospecific C-S coupling reaction of thiols and enantioenriched tertiary benzylic amines via in situ activation by methyl triflate is developed. Various enantioenriched tertiary benzylic amines, including 1-arylalkylamines, 1-tetrahydronaphthylethylamine, heterocyclic amines (e.g., 1-(thiophen-2-yl)ethanamine), and amino acid esters containing a benzylamine moiety, are highly efficient substrates, and their chirality is efficiently transferred to the products (94-99% ee). The absolute configurations of the products are predictable and follow the pattern of SN2-type substitutions; an inversion of the absolute configuration of the tertiary amines occurs during the C-S coupling reaction. Not only are various alkene-, arene-, and heteroarenethiols suitable for this C-S coupling reaction but also potassium thioacetate and sodium phenylsulfinate are as well. A plausible mechanism was proposed on the basis of the experimental results.
From the [...] joint into aryl sulfide method (by machine translation)
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Paragraph 0010; 0020, (2018/07/30)
Aryl thioether in the medical, agricultural, dye industry and the field of functional material has extensive use, human production and life are of far-reaching impact. The present invention firstly to aryl tertiary amine one-step synthesis of aryl thioether compounds, namely in the copper salt catalytic N, N - dimethyl - 1 - (hetero) aryl ethylamine with aryl dithiol to C - S coupling-synthesizing aryl thioether. The method of the invention has high yield, raw materials are easy, simple conditions, environmental protection and the like. (by machine translation)
Synthesis of thioethers via metal-free reductive coupling of tosylhydrazones with thiols
Ding, Qiuping,Cao, Banpeng,Yuan, Jianjun,Liu, Xianjin,Peng, Yiyuan
supporting information; experimental part, p. 748 - 751 (2011/03/22)
A metal-free procedure for the synthesis of thioethers is described via the base-promoted reductive coupling of tosylhydrazones with thiols through an insertion of a carbene into the S-H bond.
