In the presence of a catalytic amount of bis(acetylacetonato)cobalt(II), various olefins react smoothly with molecular oxygen and phenylsilane at room temperature to afford the corresponding alcohols in good yields under neutral conditions.
In the presence of a catalytic amount of bis(1,3-diketonato)cobalt(II), various olefins react with molecular oxygen and triethylsilane at room temperature to give the corresponding triethylsilyl peroxides in high yields under neutral conditions. The reaction provides a new method for the preparation of various peroxides directly from olefins.
In the presence of a catalytic amount of bis(dipivaloylmethanato)manganese(II) complex, the oxygenation of benzyl crotonate with molecular oxygen and phenylsilane proceeds smoothly under a mild condition to give benzyl 2-hydroxybutyrate in high yield. The reaction provides a new and convenient method for the direct preparation of various α-hydroxycarboxylic acid esters starting from α,β-unsaturated carboxylic acid esters. The influence of substituents of olefins on regioselectivity is also studied.
An efficient method for the direct peroxygenation of various olefinic compounds with molecular oxygen and triethylsilane (Et3SiH) was developed by the use of a catalytic amount of a bis(1,3-diketonato)cobalt(II) complex. According to the above method, 1-phenyl-3-triethylsilydioxybutane (2) was directly produced from 4-phenyl-1-butene (1) by means of a reaction with O2 and Et3SiH at room temperature. Styrene (3) and ethyl acrylate (5a) were also smoothly peroxygenated to give 1-phenyl-1-triethylsilyldioxyethane (4) and ethyl 2-triethylsilyldioxypropionate (6a) by using a small amount of t-BuOOH as an initiator. The successive desilylation of 6a and reduction of the resulting ethyl 2-hydroperoxypropionate (8a) afforded the corresponding alcohol, ethyl lactate (10a), in a high yield. The synthetic utility of the present peroxygenation reaction was demonstrated in the preparation of α-hydroxy esters 10a–e from several α,β-unsaturated esters 5a–e via the corresponding triethylsilyldioxy derivatives.
In the presence of a catalytic amount of bis(acetylacetonato)cobalt(II), various olefins are hydrated with oxygen and secondary alcohol to afford the corresponding alcohols together with alkanes and ketones via Oxidation-Reduction process. Effect of additives in the present hydration reaction shows that 2,6-lutidine and 2-picoline inhibit the production of alkanes in a large extent to result in the better yielding of alcohols.
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