化学
酮
三氟甲基
产量(工程)
醋酸
酒精氧化
醛
有机化学
激进的
功能群
氟
催化作用
氧化物
氧气
组合化学
聚合物
烷基
材料科学
冶金
作者
Yoichi Kadoh,Masayuki Tashiro,Kounosuke Oisaki,Motomu Kanai
标识
DOI:10.1002/adsc.201500131
摘要
Abstract The organocatalytic aerobic oxidation of electron‐deficient α‐fluoroalkyl alcohols at room temperature is described. The resulting fluoroalkyl ketones are versatile synthetic intermediates for a variety of fluorine‐containing molecules. This otherwise difficult transformation has now been accomplished by the reaction of α‐fluoroalkyl alcohols with N ‐oxyl radicals, catalytically generated from 9‐azabicyclo[3.3.1]nonan‐3‐one N ‐oxyl/nitrogen oxide (keto‐ABNO/NO x ) and oxygen in acetic acid (AcOH), affording the corresponding fluoroalkyl ketones in high yield. This operationally simple reaction can be performed under mild conditions, and was applied to a wide range of alcohols (20 examples), thus demonstrating a high functional group tolerance. Moreover, a modified one‐pot protocol based on this method was able to convert an aldehyde to a trifluoromethyl ketone on a gram scale. magnified image
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