ChemInform Abstract: Base Metal-Catalyzed Benzylic Oxidation of (Aryl)(heteroaryl)methanes with Molecular Oxygen.

ChemInform ◽  
2016 ◽  
Vol 47 (21) ◽  
Author(s):  
Hans Sterckx ◽  
Johan De Houwer ◽  
Carl Mensch ◽  
Wouter Herrebout ◽  
Kourosch Abbaspour Tehrani ◽  
...  
2016 ◽  
Vol 12 ◽  
pp. 144-153 ◽  
Author(s):  
Hans Sterckx ◽  
Johan De Houwer ◽  
Carl Mensch ◽  
Wouter Herrebout ◽  
Kourosch Abbaspour Tehrani ◽  
...  

The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP–MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.


Catalysts ◽  
2018 ◽  
Vol 8 (12) ◽  
pp. 640 ◽  
Author(s):  
Garazi Urgoitia ◽  
Raul SanMartin ◽  
María Herrero ◽  
Esther Domínguez

Csp3–H oxidation of benzylic methylene compounds is an established strategy for the synthesis of aromatic ketones, esters, and amides. The need for more sustainable oxidizers has encouraged researchers to explore the use of molecular oxygen. In particular, homogeneous metal-catalyzed aerobic oxidation of benzylic methylenes has attracted much attention. This account summarizes the development of this oxidative strategy in the last two decades, examining key factors such as reaction yields, substrate:catalyst ratio, substrate scope, selectivity over other oxidation byproducts, and reaction conditions including solvents and temperature. Finally, several mechanistic proposals to explain the observed results will be discussed.


2018 ◽  
pp. 453-488
Author(s):  
Elisabetta Alberico ◽  
Lydia K. Vogt ◽  
Nils Rockstroh ◽  
Henrik Junge

2014 ◽  
Vol 16 (5) ◽  
pp. 2344 ◽  
Author(s):  
Kexian Chen ◽  
Pengfei Zhang ◽  
Yong Wang ◽  
Haoran Li

2018 ◽  
Vol 59 (12) ◽  
pp. 1073-1079 ◽  
Author(s):  
Yuan Cai ◽  
Feng Li ◽  
Yu-Qing Li ◽  
Wu-Bin Zhang ◽  
Feng-Hua Liu ◽  
...  

ChemInform ◽  
2001 ◽  
Vol 32 (5) ◽  
pp. no-no
Author(s):  
Bastienne B. Wentzel ◽  
Maurice P. J. Donners ◽  
Paul L. Alsters ◽  
Martinus C. Feiters ◽  
Roeland J. M. Nolte

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