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Synthesis 2018; 50(08): 1629-1639
DOI: 10.1055/s-0036-1591761
DOI: 10.1055/s-0036-1591761
psp
Studies on Iron-Catalyzed Aerobic Oxidation of Benzylic Alcohols to Carboxylic Acids
Financial support from the National Basic Research Program of China (2015CB856600) is greatly appreciated.Further Information
Publication History
Received: 12 December 2017
Accepted after revision: 16 January 2018
Publication Date:
15 February 2018 (online)
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.
Key words
iron catalysis - aerobic oxidation - benzylic alcohols - carboxylic acids - electronic effects - steric effectsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591761.
- Supporting Information
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