B₂(OH)₄-Mediated Reductive Transamidation of <i>N</i>-Acyl Benzotriazoles with Nitro Compounds En Route to Aqueous Amide Synthesis

Abstract

We herein developed a reductive transamidation reaction between <i>N</i>-acyl benzotriazoles (AcBt) and organic nitro compounds or NaNO₂ under mild conditions. This protocol employed the stable and readily available B₂(OH)₄ as the reducing agent and H₂O as the ideal solvent. <i>N</i>-Deuterated amides can be synthesized when conducting the reaction in D₂O. A reasonable reaction mechanism involving bond metathesis between the AcBt amide and amino boric acid intermediate was proposed to explain the unique nature of AcBt.