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Hybrid Palladium Catalyst Assembled from Chiral Phosphoric Acid and Thioamide for Enantioselective β‐C(sp 3 )−H Arylation
Author(s) -
Jiang HuaJie,
Zhong XiuMei,
Liu ZiYe,
Geng RuiLong,
Li YangYang,
Wu YunDong,
Zhang Xinhao,
Gong LiuZhu
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004485
Subject(s) - thioamide , palladium , enantioselective synthesis , chemistry , catalysis , phosphoric acid , kinetic resolution , yield (engineering) , substrate (aquarium) , ligand (biochemistry) , combinatorial chemistry , organic chemistry , stereochemistry , medicinal chemistry , materials science , oceanography , geology , metallurgy , biochemistry , receptor
A hybrid palladium catalyst assembled from a chiral phosphoric acid (CPA) and thioamide enables a highly efficient and enantioselective β‐C(sp 3 )−H functionalization of thioamides (up to 99 % yield, 97 % ee ). A kinetic resolution of unsymmetrical thioamides by intermolecular C(sp 3 )−H arylation can be achieved with high s‐factors. Mechanistic investigations have revealed that stereocontrol is achieved by embedding the substrate in a robust chiral cavity defined by the bulky CPA and a neutral thioamide ligand.