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. Author manuscript; available in PMC: 2014 Aug 15.
Published in final edited form as: Chem Rev. 2013 Jun 20;113(8):6234–6458. doi: 10.1021/cr300527g

Table 10.

Oxidation of alcohols with copper catalysts using oxygen.

Entry Substrates Co-oxidant Ligand/Complex Additive Reaction conditions Yields # of examples Ref
1 Benzylic 1 mol% CuCl2 1.2 equiv CsCO3 Toluene, 40 °C, O2, 12 h 72–94% 9 431
2 Benzylic 1° Aliphatic graphic file with name nihms-497103-t0116.jpg 0.25 M NaOH H2O, 100 °C, 10 atm O2, 3 h 57–99% conv 5 432
3 Propargylic 10 mol% Cu-nanoparticles
10 mol% bipyridine		 PhMe, air, 80 °C, 8 h 80–95 6 433
4 Benzylic Allylic 1° Aliphatic 2° Aliphatic Graphite electrode, −0.55 V 0.03 mol% 2,2'-bisquinoline polymer 0.15 M LiClO4, 0.05 M Bu4NBF4 CH2Cl2, air, rt 85–94% 5 434
5 Benzylic 2 equiv CuCl
2 equiv phen		 2 equiv K2CO3 Benzene, reflux, O2 83–93% 3 435
6 Benzylic 2 equiv CuCl
2 equiv phen		 2 equiv K2CO3 Benzene, reflux, O2 65–86% 4 436
7 Benzylic 5 mol% Cu(OAc)2
5 mol% phen		 1:1 DMF/Benz ene, reflux, O2, 2 h 54–70% 3 437
8 Benzylic graphic file with name nihms-497103-t0117.jpg NaOH (pH 13.2) H2O, 80 °C, 10 bar O2, 54–74% 5 438