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Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst
Author(s) -
Utsumi Tatsuki,
Noda Kenta,
Kawauchi Daichi,
Ueda Hirofumi,
Tokuyama Hidetoshi
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000663
Subject(s) - chemistry , nitrile , primary (astronomy) , catalysis , silylation , allylamine , organic chemistry , salt (chemistry) , ammonium , halogen , combinatorial chemistry , polymer , alkyl , polyelectrolyte , physics , astronomy
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 .