Research Article

Decarboxylative borylation

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Science  13 Apr 2017:
DOI: 10.1126/science.aam7355

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The widespread use of alkyl boronic acids and esters is frequently hampered by the challenges associated with their preparation. Herein we describe a simple and practical method to rapidly access densely functionalized alkyl boronate esters from abundant carboxylic substituents. This broad-scope Ni-catalyzed reaction uses the same activating principle as amide bond formation to replace a carboxylic acid with a boronate ester. Application to peptides allowed expedient preparations of α-amino boronic acids, often with high stereoselectivity, facilitating the synthesis of both FDA approved alkyl boronic acid drugs (Velcade and Ninlaro) as well as a boronic acid version of the iconic antibiotic vancomycin. The reaction also enabled the discovery and extensive biological characterization of potent elastase inhibitors which may have a strategic advantage due to their covalent-reversible binding properties.

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