Regio- and enantioselective remote hydroarylation using a ligand-relay strategy

Yuli He; Jiawei Ma; Huayue Song; Yao Zhang; Yong Liang; You Wang; Shaolin Zhu

doi:10.1038/s41467-022-30006-2

Regio- and enantioselective remote hydroarylation using a ligand-relay strategy

Nat Commun. 2022 May 5;13(1):2471. doi: 10.1038/s41467-022-30006-2.

Authors

Yuli He¹, Jiawei Ma¹, Huayue Song¹, Yao Zhang¹, Yong Liang², You Wang³, Shaolin Zhu^{4

5}

Affiliations

¹ State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.
² State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China. yongliang@nju.edu.cn.
³ State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China. wangyou@nju.edu.cn.
⁴ State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China. shaolinzhu@nju.edu.cn.
⁵ School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, China. shaolinzhu@nju.edu.cn.

Abstract

The design of a single complicated chiral ligand to well-promote each step of an asymmetric cascade reaction is sometimes a formidable challenge in transition metal catalysis. In this work, a highly regio- and enantioselective Ni-catalysed migratory hydroarylation relay process has been achieved with the combination of two simple ligands, one which accomplishes chain-walking and the other causing asymmetric arylation. This formal asymmetric C(sp³)-H arylation provides direct access to a wide range of structurally diverse chiral 1,1-diarylalkanes, a structural unit found in a number of bioactive molecules. The value of this strategy was further demonstrated by the Ni-catalysed migratory asymmetric 1,3-arylboration.

Publication types

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

MeSH terms

Catalysis
Ligands
Stereoisomerism
Transition Elements*

Substances

Ligands
Transition Elements