Hybrid Palladium Catalyst Assembled from Chiral Phosphoric Acid and Thioamide for Enantioselective β‐C(sp 3 )−H Arylation | Zendy

Jiang HuaJie | Zendy; Zhong XiuMei | Zendy; Liu ZiYe | Zendy; Geng RuiLong | Zendy; Li YangYang | Zendy; Wu YunDong | Zendy; Zhang Xinhao | Zendy; Gong LiuZhu | Zendy

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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 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.202004485

Subject(s) - thioamide , enantioselective synthesis , palladium , phosphoric acid , catalysis , chemistry , yield (engineering) , kinetic resolution , substrate (aquarium) , stereochemistry , organic chemistry , combinatorial chemistry , materials science , oceanography , geology , metallurgy

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.

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