Frontispiece: Synthetic Approaches to Triarylboranes from 1885 to 2020

Abstract

The review article presented by T. B. Marder et al. on page 7043, summarizes the synthetic developments that have been made in the synthesis of triarylboranes throughout the years from their first appearance in 1885 to the present. It is shown that, over time, developments in other fields of research enriched triarylborane chemistry by developing new organometallic reagents or boron sources, which led to new synthetic strategies and opened the door for diverse applications. Investigation of reactivities and other molecular properties of triarylboranes led to the first commercially available products by the middle of the 20th century. With increasing interest in this field of research, new potential applications of such compounds continue to arise. This review article aims to provide guidance for researchers to find the best synthetic strategy for preparing new compounds containing the triarylborane motif.

Remote Back Strain: A Strategy for Modulating the Reactivity of Triarylboranes

“…In the latter case, strategies that substitute meta -F and/or para -F atoms in B(C 6 F 5 ) 3 with more- or less-electron-withdrawing substituents have been applied to prepare more- or less-electrophilic triarylborane derivatives through regulation of their electron affinity (i.e., their intrinsic Lewis acidity). 1a b , 3 5 Strategies that regulate the steric repulsion between Lewis base (LB) counterparts (front strain) through modulation of the size of the ortho -substituents on the aryl groups in the triarylborane have also been widely explored (Figure 1 ; left). 6 Decreasing the front strain through the introduction of smaller ortho -substituents should enhance the global and effective Lewis acidity, 3 5 whereas increasing this strain should result in the opposite outcome.…”