Synthesis ( IF 2.2 ) Pub Date : 2018-02-15 , DOI: 10.1055/s-0036-1591761 Shengming Ma 1, 2 , Xingguo Jiang 1, 3
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Abstract
A comprehensive study on aerobic oxidation of benzylic alcohols to carboxylic acids with a catalytic amount each of Fe(NO3)3·9H2O, TEMPO, and KCl is conducted. Various synthetically useful functional groups are well tolerated in the reaction. Distinct electronic and steric effects are observed in the reaction: electron-withdrawing groups accelerate the reaction while electron-donating groups make the reaction slower, and ortho-substituted substrates react slower than meta-substituted substrates. Several large-scale reactions (100 mmol) are conducted using a slow air flow of 30 mL/min to demonstrate the practicality of this method in an academic laboratory.
A comprehensive study on aerobic oxidation of benzylic alcohols to carboxylic acids with a catalytic amount each of Fe(NO3)3·9H2O, TEMPO, and KCl is conducted. Various synthetically useful functional groups are well tolerated in the reaction. Distinct electronic and steric effects are observed in the reaction: electron-withdrawing groups accelerate the reaction while electron-donating groups make the reaction slower, and ortho-substituted substrates react slower than meta-substituted substrates. Several large-scale reactions (100 mmol) are conducted using a slow air flow of 30 mL/min to demonstrate the practicality of this method in an academic laboratory.
中文翻译：
铁催化苯甲醇中的好氧氧化为羧酸的研究
摘要
进行了一项综合研究，将苄醇有氧氧化为催化量为Fe（NO 3）3 ·9H 2 O，TEMPO和KCl的羧酸。反应中对各种合成有用的官能团的耐受性良好。在反应中观察到明显的电子和空间效应：吸电子基团加速反应，而供电子基团使反应更慢，邻位取代的底物比间位取代的底物反应慢。使用30 mL / min的缓慢气流进行了几次大规模反应（100 mmol），以证明该方法在学术实验室中的实用性。
进行了一项综合研究，将苄醇有氧氧化为催化量为Fe（NO 3）3 ·9H 2 O，TEMPO和KCl的羧酸。反应中对各种合成有用的官能团的耐受性良好。在反应中观察到明显的电子和空间效应：吸电子基团加速反应，而供电子基团使反应更慢，邻位取代的底物比间位取代的底物反应慢。使用30 mL / min的缓慢气流进行了几次大规模反应（100 mmol），以证明该方法在学术实验室中的实用性。
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