B<sub>2</sub>(OH)<sub>4</sub>-Mediated Reductive Transamidation of <i>N</i>-Acyl Benzotriazoles with Nitro Compounds En Route to Aqueous Amide Synthesis
Jin Bai, Shangzhang Li, Riqian Zhu, Yang Li, Wanfang Li
Abstract
We herein developed a reductive transamidation reaction between N -acyl benzotriazoles (AcBt) and organic nitro compounds or NaNO 2 under mild conditions. This protocol employed the stable and readily available B 2 (OH) 4 as the reducing agent and H 2 O as the ideal solvent. N -Deuterated amides can be synthesized when conducting the reaction in D 2 O. 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.
Topics & Concepts
ChemistryAmideNitroCombinatorial chemistryAqueous solutionReaction mechanismOrganic chemistryCatalysisAlkylChemical Synthesis and AnalysisAdvanced Synthetic Organic ChemistryAsymmetric Hydrogenation and Catalysis