Recently, Professor Jiang Zhiyong’s team from  School of Chemistry and Chemical Engineering of Henan Normal University has made new progress in the field of asymmetric photochemical reactions. Using pyridinyl-triazole and boronic acid as substrates, they achieved an asymmetric photocatalytic reaction by utilizing chiral primary amine catalysis to synthesize triaryl methane compounds. The research findings have been published in Journal of the American Chemical Society, an international chemistry journal. Jiang Chenyang and Meng Youlan, both PhD candidates from School of Chemistry and Chemical Engineering, are the co-first authors of the paper. Professor Jiang Zhiyong and Dr. Cao Shanshan, a young faculty member, serve as the corresponding authors of this study.

Triaryl methane compounds have found extensive applications in medicinal chemistry, fluorescence probes, dyes, and nonlinear optical materials in recent years. However, existing methods for asymmetric synthesis of triaryl methanes containing electron-deficient nitrogen heteroaromatic rings face several limitations, such as few reaction examples, difficulty in functional group regulation, and challenges in introducing deuterium.

Professor Jiang’s team utilized a novel chiral pyrrole-derived primary amine catalyst (C1), which is derived from a commercially available chiral diamine. Under optimized reaction conditions, the reaction achieves a high yield of up to 93% and an enantiomeric excess (ee) of as much as 96%. This strategy demonstrates strong versatility, applicable across various substrates. This study not only provides a general and efficient method for synthesizing chiral triaryl methane compounds but also expands the toolbox for chiral hydrogen bond catalysis. It represents the first application of 1,4-boryl migration in asymmetric synthesis, laying a solid foundation for developing more useful asymmetric reactions, and holds promise for advancing related fields such as medicinal chemistry and materials science.

Paper Link: https://pubs.acs.org/doi/10.1021/jacs.4c16811
(School of Chemistry and Chemical Engineering, Jiang Tao & Wang Manman)