U.S. flag

An official website of the United States government

Dot gov

Official websites use .gov
A .gov website belongs to an official government organization in the United States.


Secure .gov websites use HTTPS
A lock ( ) or https:// means you’ve safely connected to the .gov website. Share sensitive information only on official, secure websites.


Main content area

A Pseudodearomatized PN³P*Ni–H Complex as a Ligand and σ-Nucleophilic Catalyst

Huaifeng Li, Théo P. Gonçalves, Jinsong Hu, Qianyi Zhao, Dirong Gong, Zhiping Lai, Zhixiang Wang, Junrong Zheng, Kuo-Wei Huang
Journal of organic chemistry 2018 v.83 no.24 pp. 14969-14977
Lewis bases, acylation, alcohols, aldehydes, amines, carbon dioxide, catalytic activity, chemical structure, cycloaddition reactions, dehydrogenation, epoxides, heterocyclic nitrogen compounds, imines, ligands, organic chemistry, organocatalysts
In contrast to the conventional strategy of modifying the reactivities and selectivities of the transition metal and organocatalysts by varying the steric and electronic properties of organic substituent groups, we hereby demonstrate a novel approach that the sigma (σ) nucleophilicity of the imine arm can be significantly enhanced in a pseudodearomatized PN³P* pincer ligand platform to reach unprecedented N-heterocyclic carbene-like reactivity. Accordingly, the imine arm of the PN³P*Ni–H pincer complex efficiently catalyzes the hydrosilylation of aldehydes, cycloaddition of carbon dioxide (CO₂) to epoxides, and serves as a ligand in the Ru-catalyzed dehydrogenative acylation of amines with alcohols.