Bimetallic Palladium/Cobalt Catalysis for Enantioselective Allylic C-H Alkylation via a Transient Chiral Nucleophile Strategy

Hongkai Wang; Yang Xu; Fangqing Zhang; Yangbin Liu; Xiaoming Feng

doi:10.1002/anie.202115715

Bimetallic Palladium/Cobalt Catalysis for Enantioselective Allylic C-H Alkylation via a Transient Chiral Nucleophile Strategy

Angew Chem Int Ed Engl. 2022 Mar 14;61(12):e202115715. doi: 10.1002/anie.202115715. Epub 2022 Feb 3.

Authors

Hongkai Wang^{1

2}, Yang Xu², Fangqing Zhang¹, Yangbin Liu², Xiaoming Feng^{2

3}

Affiliations

¹ Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen, 518055, China.
² Shenzhen Bay Laboratory, Shenzhen, 518055, China.
³ Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.

PMID: 35040550
DOI: 10.1002/anie.202115715

Abstract

An asymmetric allylic C-H functionalization has been developed by making use of transient chiral nucleophiles, as well as bimetallic synergistic catalysis with an achiral Pd⁰ catalyst and a chiral N,N'-dioxide-Co^II complex. A variety of β-ketoesters and N-Boc oxindoles coupled with allylbenzenes and aliphatic terminal alkenes were well tolerated, furnishing the desired allylic alkylation products in high yields (up to 99 %) with excellent regioselectivities and enantioselectivities (up to 99 % ee).

Keywords: Asymmetric Alkylation; Bimetallic Catalysis; Chiral N,N′-dioxide Ligands; Cobalt Complexes; Transient Chiral Nucleophiles.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Catalysis
Cobalt*
Palladium*
Stereoisomerism

Substances

Cobalt
Palladium