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

Chemical Science Pub Date: 2021-07-23 DOI: 10.1039/D1SC02937A

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.

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