Direct Oxidation of Primary Alcohols to Carboxylic Acids

Abstract

Oxidation of primary alcohols to carboxylic acids is a fundamental transformation in organic chemistry, yet despite its simplicity, extensive use, and relationship to pH, it remains a subject of active research for synthetic organic chemists. Since 2013, a great number of new methods have emerged that utilize transition-metal compounds as catalysts for acceptorless dehydrogenation of alcohols to carboxylates. The interest in this reaction is explained by its atom economy, which is in accord with the principles of sustainability and green chemistry. Therefore, the methods for the direct synthesis of carboxylic acids from alcohols is ripe for a modern survey, which we provide in this review.1 Introduction2 Thermodynamics of Primary Alcohol Oxidation3 Oxometalate Oxidation4 Transfer Dehydrogenation5 Acceptorless Dehydrogenation6 Electrochemical Methods7 Outlook

Catalytic Oxidations with ortho-Substituted Modified IBXs

“…Oxidation of alcohols to carbonyl compounds is an important transformation that is not only of general interest but also quintessential in organic synthesis. 42 43 Because of the growing demand for mild, inexpensive, and eco-friendly reactions in contemporary chemistry, oxidations with IBX are of paramount importance. Although IBX is a vital reagent in the arsenal of an organic chemist for selective oxidation of alcohols to aldehydes/ketones, 9 its stoichiometric use, as mentioned earlier, is plagued by problems such as explosiveness and insolubility.…”

FDU-12-C encapsulatedt-Bu(R,R)CoII(salen) as a cathode catalyst for asymmetric electrocarboxylation of 1-phenylethyl chloride with CO2

“…Among them, optically active carboxylic acids have significant applications in the synthesis of polymers and pharmaceuticals. 22 In addition, considering that chiral carboxylic acids are usually obtained by hydroformylation of unsaturated hydrocarbons 23 and oxidation of chiral alcohols, 24 scientists are very keen to use CO 2 for direct asymmetric electrocarboxylation, which can not only avoid the use of toxic and harmful CO as well as oxidants, but also make better use of carbon. On the other hand, the electrocatalytic enantioselective binding of CO 2 with organic compounds would provide great opportunities to expand our academic and pharmaceutical laboratory studies for preparing chiral molecules from simple carbon feedstocks.…”

External Catalyst- and Additive-Free Photo-Oxidation of Aromatic Alcohols to Carboxylic Acids or Ketones Using Air/O2

“…The selective oxygenation of aromatic alcohols to acids, which are significant raw materials and intermediates for the production of food preservatives, dyes, plasticizers, and sugars, is a fundamental reaction in organic synthesis [ 1 , 2 , 3 , 4 , 5 , 6 ]. For example, 1, 4-terephthalic acid is an important monomer in the synthesis of polyethylene terephthalate (PET, commonly known as polyester resin), whose annual global consumption amounts to about 13 million tons.…”