Pyrimidine-directed metal-free C–H borylation of 2-pyrimidylanilines: a useful process for tetra-coordinated triarylborane synthesis

Abstract

Convenient, easily handled, laboratory friendly, robust approaches to afford synthetically important organoboron compounds are currently of great interest to researchers. Among the various available strategies, a metal-free approach would be overwhelmingly accepted, since the target boron compounds can be prepared in a metal-free state. We herein present a detailed study of the metal-free directed ortho-C–H borylation of 2-pyrimidylaniline derivatives. The approach allowed us to synthesize various boronates, which are synthetically important compounds and various four-coordinated triarylborane derivatives, which could be useful in materials science as well as Lewis-acid catalysts. This metal-free directed C–H borylation reaction proceeds smoothly without any interference by external impurities, such as inorganic salts, reactive functionalities, heterocycles and even transition metal precursors, which further enhance its importance.