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Arylation of Axially Chiral Phosphorothioate Salts by Dinuclear Pd I Catalysis
Author(s) -
Chen XiangYu,
Pu Maoping,
Cheng HongGang,
Sperger Theresa,
Schoenebeck Franziska
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201906063
Subject(s) - aryl , catalysis , chemistry , combinatorial chemistry , dimer , organic chemistry , computational chemistry , stereochemistry , alkyl
S‐aryl phosphorothioates are privileged motifs in pharmaceuticals, agrochemicals, and catalysts; yet, the challenge of devising a straightforward synthetic route to enantioenriched S‐aryl phosphorothioates has remained unsolved to date. We demonstrate herein the first direct C−SP(=O)(OR′)(OR′′) coupling of diverse and chiral phosphorothioate salts with aryl iodides, enabled by an air‐ and moisture‐stable Pd I dimer. Our mechanistic and computational data suggest distinct dinuclear Pd I catalysis to be operative, which allows for operationally simple couplings with broad scope and full retention of stereochemistry.