Synthesis of (Enantioenriched) Dibenzyl Thioethers and Disulfides via S<sub>N</sub>2 Nucleophilic Substitution of Quaternary Ammonium Salts
Qinqin Tang, Fuhai Li, Hongyi Chen, Xianjie Yin, Yan Tang, Qingle Zeng
Abstract
Abstract A synthetic protocol of dibenzyl thioethers and dibenzyl disulfides via S N 2 nucleophilic substitution of quaternary ammonium salts and sodium sulfide nonahydrate and disodium disulfide under mild condition is described. In particular, if quaternary ammonium salts synthesized from enantiomerically enriched amines are adopted, highly enantioenriched dibenzyl thioethers (92–95% ee) with reverse configurations to their enantioenriched quaternary ammonium salts are obtained.
Topics & Concepts
ChemistryAmmoniumNucleophilic substitutionNucleophileSulfideQuaternarySodium sulfideEnantioselective synthesisOrganic chemistryMedicinal chemistryCatalysisBiologyPaleontologySulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsPhenothiazines and Benzothiazines Synthesis and Activities