2024 Volume 82 Issue 11 Pages 1097-1106
Herein we summarize our recent progress on the design, synthesis, and catalytic application of triarylboranes. We demonstrated that structurally well-characterized triarylboranes catalyzed the hydrogenation of N-heteroaromatics and carbonyl compounds when crude H2 (a mixture of H2, CO, CO2, and CH4) was directly used as reductant. In addition, we proposed a concept of ‘remote back strain’ to finely tune the Lewis acidity of triarylboranes by regulating the stability of Lewis base-borane adducts via an intramolecular repulsion between the meta-substituents on the aryl groups. Such approaches were eventually combined with machine learning and efficiently assisted the optimization of boranes that catalyzed the reductive alkylation of multiply-substituted aniline derivatives, including amino acids and peptides, using H2 as reductant. These results manifest a new aspect of main-group catalysis beyond its application as a simple alternative to well-established transition metal-catalyzed processes.
