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Described herein is the preparation of oxalyl boronate building blocks and their application for the construction of heterocycles. The oxalyl unit, readily accessible through commercially available starting materials, enables a modular approach for the synthesis of imidazoles. A variety of aromatic, heteroaromatic, and alkyl carboxaldehydes were condensed with oxalyl boronates to afford substituted boryl imidazoles in a regiocontrolled fashion. Subsequent palladium-catalyzed cross-coupling with haloarenes furnished the desired trisubstituted imidazole scaffolds. To demonstrate the utility of these scaffolds, potent inhibitors of the serine/threonine-protein kinase STK10 were synthesized.

Original publication

DOI

10.1002/anie.201611006

Type

Journal article

Journal

Angew Chem Int Ed Engl

Publication Date

22/05/2017

Volume

56

Pages

6264 - 6267

Keywords

biological activity, boron, cross-coupling, heterocycles, synthetic methods