Synthesis of (Enantioenriched) Dibenzyl Thioethers and Disulfides via SN2 Nucleophilic Substitution of Quaternary Ammonium Salts

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.

Automated summary

A synthetic protocol for dibenzyl thioethers and dibenzyl disulfides via S(N)2 nucleophilic substitution is described, using quaternary ammonium salts and sodium sulfide nonahydrate. Highly enantioenriched dibenzyl thioethers (92-95% ee) can be obtained by adopting quaternary ammonium salts synthesized from enantiomerically enriched amines.