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

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 re...

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Published inChemical communications (Cambridge, England) Vol. 56; no. 85; pp. 1329 - 1332
Main Authors Li, Fuhai, Wang, Dan, Chen, Hongyi, He, Ze, Zhou, Lihong, Zeng, Qingle
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 27.10.2020
Royal Society of Chemistry
Subjects
Amines
Aromatic compounds
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Disulfides
NMR
Nuclear magnetic resonance
Physical Sciences
Quaternary ammonium salts
Science & Technology
Selenides
Synthesis
Transition metals
BORONIC ACIDS
SUBSTITUTION
IN-SITU ACTIVATION
CROSS-COUPLINGS
RHODIUM
AMINES
SELENIDES
INHIBITORS
AMMONIUM-SALTS
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Summary: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. Benzylic thioethers and selenoethers with high enantiopurity and yield were synthesized via transition-metal-free coupling reactions of benzylic trimethylammonium salts.
Bibliography:C NMR and MS characterization data and spectra of all products. See DOI
1
H and
13
10.1039/d0cc05633b
Electronic supplementary information (ESI) available: Experimental procedures
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ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc05633b