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Selective aerobic oxidation of benzylic and allylic alcohols catalyzed by Cu(OAc)2/TEMPO/Et2NH

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Title Selective aerobic oxidation of benzylic and allylic alcohols catalyzed by Cu(OAc)2/TEMPO/Et2NH
 
Creator Pasupuleti, Bala Gangadhar
Gogoi, Achinta
Bez, Ghanashyam
 
Subject Cu(OAc)2
TEMPO
Selective aerobic oxidation
Benzylic alcohols
Allylic alcohols
 
Description 589-597
Selective oxidation of benzylic and allylic alcohols to their corresponding aldehyde/ketone derivative without affecting saturated alcohols is still a challenging endeavor in organic synthesis. Various metal complexes, especially the copper complexes in the presence of TEMPO are being used very often for such transformations under aerobic conditions, but they are not selective to allylic and benzylic alcohols. The use of copper salt for oxidation of alcohols in the absence of a ligand are very scarcely studied except for the one catalyzed by CuCl/TEMPO where chloride inhibition and lack of selective oxidation have been noted upon use of CuCl2. Herein we report a Cu(OAc)2 catalyzed and TEMPO mediated selective aerobic oxidation of benzylic and allylic alcohols to aldehyde/ketone in the presence of Et2NH. The method avoids pre-synthesis of the catalyst as in the case of Cu(II)/(I) complexes/TEMPO catalyzed oxidation reactions, requires low catalyst loading, employs cheaper copper salt, and gives excellent selectivity for oxidation of benzylic and allylic alcohols.
 
Date 2021-04-15T05:03:07Z
2021-04-15T05:03:07Z
2021-04
 
Type Article
 
Identifier 0975-0983(Online); 0376-4699(Print)
http://nopr.niscair.res.in/handle/123456789/57105
 
Language en_US
 
Rights CC Attribution-Noncommercial-No Derivative Works 2.5 India
 
Publisher NISCAIR-CSIR, India
 
Source IJC-B Vol.60B(04) [April 2021]