Secondary benzylic alcohols and diarylmethanols are common structural motifs of biologically active medicinally relevant compounds. Here we report their enantioselective synthesis by ?-arylation primary aliphatic under sequential catalysis integrating a Ru-catalyzed hydrogen transfer oxidation nucleophilic addition. The method can be applied to various aryl nucleophiles tolerating range functio...

Para-Aminobenzoic acid is supported on silica gel via reaction of activated silica gel and p-aminobenzoic acid which is then converted to its manganese and cobalt salts. A mixture of the manganese and cobalt salts of the acid is used to catalyze allylic and benzylic alcohols to their corresponding carbonyl compounds in reasonable yields using oxygen or air. Reactions are clean and the catal...

The thermal oxidative degradation of polyethylene glycol (PEG) is known to occur in an oxygen atmosphere at elevated temperatures. In this study, PEG radicals assumed to result from thermal oxidative degradation are successfully applied, in combination with compressed CO(2), to initiate a range of free-radical reactions, such as selective formylation of primary and secondary aliphatic alcohols,...

An efficient methodology to oxidize benzylic and cinnamyl alcohols to their corresponding nitriles in excellent yields has been developed. This methodology employs DDQ as an oxidant and TMSN(3) as a source of nitrogen in the presence of a catalytic amount of Cu(ClO(4))(2)·6H(2)O.

A hydrogen-transfer strategy for the catalytic functionalization of benzylic alcohols via electronic arene activation, accessing a diverse range of bespoke diaryl ethers and aryl amines in excellent isolated yields (38 examples, 70% average yield), is reported. Taking advantage of the hydrogen-transfer approach, the oxidation level of the functionalized products can be selected by judicious cho...

A direct catalytic substitution of various allylic and benzylic alcohols with synthetically useful, but acid-sensitive Boc, Bus, and Dios protected amine nucleophiles, which have not been well utilized for Lewis acid catalysis, with various functionalities (OTBS, OTHP, etc.) was efficiently catalyzed by 1 mol% of Au(III) under mild conditions.

The acid-catalyzed three-component reaction of terminal alkynes, benzylic alcohols, and simple arenes provides convenient and atom-economic access to an array of both Z- and E-isomers of trisubstituted alkenes with excellent stereoselectivity by switching reaction temperature and acidic catalysts.

The Bu4NI-catalyzed reaction of ketones with benzylic alcohols was achieved, leading to alfa-acyloxycarbonyl compounds in moderate to good yields. This metal-free procedure featured the employment of facilely and commercially available starting materials and TBHP as a clean oxidant with high atom economy.

A novel strategy for catalytic oxidation of a variety of benzylic, allylic, propargylic, and aliphatic alcohols to the corresponding aldehydes or ketones by an in situ formed porphyrin-inspired manganese complex in excellent yields (up to 99%) has been successfully developed.

This personal account summarizes our recent developments in gold-catalyzed direct substitutions on propargylic (allylic, benzylic) alcohols, with various nucleophiles (and bi-nucleophiles) based on the σ- and/or π-acidity of gold(III) complexes. Synthetic developments are also briefly described.