Synthesis 2018; 50(08): 1629-1639
DOI: 10.1055/s-0036-1591761
psp
© Georg Thieme Verlag Stuttgart · New York

Studies on Iron-Catalyzed Aerobic Oxidation of Benzylic Alcohols to Carboxylic Acids

Xingguo Jiang
a  State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China   Email: [email protected]
b  University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
a  State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China   Email: [email protected]
c  Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. of China
› Author Affiliations
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.

Supporting Information

 
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