Jump to main content
Jump to site search


Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides

Author affiliations

Abstract

A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72–94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94–99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts.

Graphical abstract: Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides

Back to tab navigation

Supplementary files

Article information


Submitted
19 Aug 2020
Accepted
10 Sep 2020
First published
10 Sep 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides

F. Li, D. Wang, H. Chen, Z. He, L. Zhou and Q. Zeng, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC05633B

Social activity

Search articles by author

Spotlight

Advertisements