Organic Chemistry

Enantioselective para-C(sp2)-H Functionalization of Alkyl Benzene Derivatives via Cooperative Catalysis of Gold/Chiral Bronsted Acid



Herein, we developed an asymmetric para-C(sp2)-H bond functionalization of alkyl benzene derivatives via cooperative catalysis of gold and chiral phosphoric acid, leading to synthetically useful diaryl chiral centers. In this transformation, chiral phosphoric acid, ligand, and molecular sieves were all crucial for enantioselectivity control. The salient features of this protocol include mild conditions, high efficiency, readily avail-able starting materials, highly chemo- and site- as well as enantioselective aromatic C−H functionalization, broad substrate scope, and exten-sive applications of the chiral products. The mechanistic studies showed that one gold complex and two CPAs might be involved in the chiral induction.


Thumbnail image of JACS lxs C-H 2022.05.03.pdf

Supplementary material

Thumbnail image of SI lxs 2022-5-3.pdf
supporting information