Nitrile Synthesis by Aerobic Oxidation of Primary Amines and <i>in</i> <i>situ</i> Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst
Tatsuki Utsumi, Kenta Noda, Daichi Kawauchi, Hirofumi Ueda, Hidetoshi Tokuyama
Abstract
Abstract Herein, a Grubbs‐catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β‐disubstituted amines, allylamine, benzylamines, and α‐amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH 4 OAc in situ . magnified image
Topics & Concepts
ChemistryNitrilePrimary (astronomy)CatalysisSilylationAllylamineOrganic chemistrySalt (chemistry)AmmoniumHalogenCombinatorial chemistryPolymerPolyelectrolyteAstronomyAlkylPhysicsChemical Synthesis and AnalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods