Abstract
This work reports an efficient method for the oxidation reaction of aliphatic, aromatic allylic, and benzylic alcohols into aldehydes catalyzed by the cyclopentadienyl ruthenium(II) complex (RuCpCl(PPh3)2) with bubbled O2. Through further optimizing controlled studies, the tendency order of oxidation reactivity was determined as follows: benzylic alcohols > aromatic allylic alcohols >> aliphatic alcohols. In addition, this method has several advantages, including a small amount of catalyst (0.5 mol%) and selective application of high discrimination activity of aliphatic, aromatic allylic, and benzylic alcohols.
Highlights
Oxidation reactions are very useful functional transformations in organic synthesis [1, 2]
Benzyl alcohol 1a is an important precursor for organic synthesis and a useful solvent because of its polarity, low toxicity, mildly pleasant aromatic odor, and low vapor pressure [52,53,54]. e chemoselective oxidation property of compound 1a was very useful in functional transformations for the preparation of aldehydes [55, 56] and their dicarboxyl analogues [57, 58]
We preliminarily investigated a versatile oxidation method for compound 1a with 0.5 mol% amount of the cyclopentadienyl ruthenium(II) complex (RuCpCl(PPh3)2) catalyst with bubbled O2 in CH2Cl2 solution at reflux for 24 h
Summary
Oxidation reactions are very useful functional transformations in organic synthesis [1, 2]. Many of the metalbased oxidizing reagents have been developed to achieve the e cient oxidation of alcohols such as PI Au [3], ARP-Pt [4], Ru/Al2O3 [5, 6], Pd/HAP [7, 8], Au-Pd/TiO2 [9], and HB Ru [10] These catalysts are generally di cult to obtain because of their expensive cost and harsh production. The rare earth elements have occupied an especially important place in the past two decades because of their high reactivity in various catalytic processes [33,34,35,36,37,38,39] One of these rare elements is ruthenium. Some species of ruthenium have been widely developed and used as e cient catalysts for oxidation reactions [40, 41]
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