Novel C-H functionalization reaction with tandem catalyst developed

January 6, 2023

New promising approach for efficient CO2 utilization

The RIKEN CSRS has developed a tandem copper catalyst that enables the borylation and carboxylation of alkenes to carboxylate alkenyl C-H bonds with carbon dioxide (CO2).

Carboxylation of alkenyl C-H bonds using CO2 is a convenient approach to synthesizing corresponding esters and carboxylic acids, while it had previously been applied only to alkenes with specific substrates.

The research team used a copper catalyst to catalyze the reaction of some easily accessible chemicals, including alkenes, CO2, boron compounds, and lithium alkoxide, and found that the borylation and carboxylation of alkenes proceed tandemly (in a domino falling manner) to carboxylate alkenyl C-H bonds selectively in one pot. This reaction can be applied to alkenes with various functional groups, having an advantage of wide applicability to different substrates.

This study may provide an essential guide for the design and development of new metal catalysts and lead to the development of new approaches for effective CO2 utilization.

Original article
Journal of the American Chemical Society doi:10.1021/jacs.2c10754
H. Sahoo, L. Zhang, J. Cheng, M. Nishiura, Z. Hou,
"Auto-Tandem Copper-Catalyzed Carboxylation of Undirected Alkenyl C-H Bonds with CO2 by Harnessing β-Hydride Elimination".
Zhaomin Hou; Group Director
Harekrishna Sahoo; Postdoctoral Researcher
Liang Zhang; Senior Research Scientist
Masayoshi Nishiura; Senior Research Scientist
Advanced Catalysis Research Group