Beilstein J. Org. Chem.2011,7, 396–403, doi:10.3762/bjoc.7.51
by Markó et al., the yields are relatively lower.
Keywords: allenicketone; allenol; Cu(I) catalyst; oxidation; Introduction
The oxidation of alcohols is one of many fundamental reactions in organic synthesis [1][2]. Usually, stoichiometric oxidants such as MnO2 [3], PCC [4], PDC [4], etc. were
of 1-naphthyl-substituted 1h afforded 2h in 74% yield (Table 5, entry 8). Tri-substituted allenic alcohol 1j was also oxidized to the corresponding allenicketone 2j in 91% yield (Table 5, entry 10).
The reaction may be easily carried out on a 1 g scale: the oxidation of allenol 1k afforded the
corresponding allenicketone 2k in 74% yield in 12 hours with just 10 mol % of CuCl and 5 mol % each of 1,10-phenanthroline and 2,2'-bipyridine (Scheme 1).
When the reaction of 1-alkyl-substituted-2,3-allenols oxidation was conducted under 1 atm of oxygen at 60 °C, 81% of conversion was observed and the