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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
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2020-07-14 , DOI: 10.1002/adsc.202000663
Tatsuki Utsumi 1 , Kenta Noda 1 , Daichi Kawauchi 1 , Hirofumi Ueda 1 , Hidetoshi Tokuyama 1
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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 NH4OAc in situ.

中文翻译:

有氧氧化伯胺和原位生成的胺与格鲁布斯催化剂从醛和铵盐中合成腈

本文报道了格鲁布斯催化的伯胺的需氧氧化合成腈的路线。该反应可容纳多种底物,包括简单的伯胺,空间受阻的β,β-二取代胺,烯丙胺,苄胺和α-氨基酯。还指出了与各种官能团的反应相容性,特别是与烯烃,炔烃,卤素,酯,甲硅烷基醚和游离羟基的相容性。腈也是通过醛和NH 4 OAc原位生成的亚胺氧化合成的。
更新日期:2020-09-05
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