Direct oxidation of primary alcohols to the corresponding carboxylic acids is performed highly efficiently at room temperature with anhydrous tert-butyl hydroperoxide in the presence of a catalytic amount of easily available CuCl under ligand free conditions in acetonitrile. Benzylic alcohols are more reactive than aliphatic alcohols, and these benzylic alcohols are selectively oxidized to the corresponding acids in the presence of aliphatic alcohols such as 1-octanol and 1-decanol. © 2008 Elsevier Ltd. All rights reserved.

Govindasamy Sekar

Department Of Chemistry

Sreedevi Mannam

acetonitrile

carboxylic acid

COPPER CHLORIDE

DECANOL

OCTANOL

tert butyl hydroperoxide

Alcohol oxidation

article

catalysis

chemical reaction

Room temperature

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Tetrahedron Letters

A copper-catalyzed one-pot strategy for the synthesis of α-ketoamides from 1-arylethanols is described. This triple oxidation of 1-arylethanols involves alcohol oxidation, sp3 C-H oxidation, and oxidative amidation with amines. The protocol is highly efficient, delivering α-ketoamides in good to excellent yields.

Synthesis (Germany)

Copper-catalyzed one-pot synthesis of α-ketoamides from 1-arylethanols

A new procedure for the selective and direct oxidation of aliphatic primary alcohols having substitution at - and -positions to corresponding carboxylic acids was developed using a catalytic amount of ligand and additive-free CuCl with anhydrous tBuOOH in acetonitrile solvent under very mild reaction conditions. This procedure is very simple and mild and works efficiently without any additives at room temperature. © 2010 Taylor & Francis Group, LLC.

Synthetic Communications

Efficient CuCl-catalyzed selective and direct oxidation of β- And γ-substituted aliphatic primary alcohols to carboxylic acids

A wide range of 2-aryl or 2-alkyl-substituted benzothiazoles are synthesized through intramolecular C(aryl)-S bond forming-cyclization using copper(II)-BINAM-catalyzed coupling of less reactive N-(2-chlorophenyl) benzo or alkylthioamide under mild reaction conditions (82 °C). © 2010 Elsevier Ltd. All rights reserved.

An efficient copper(II)-catalyzed synthesis of benzothiazoles through intramolecular coupling-cyclization of N-(2-chlorophenyl)benzothioamides

A wide range of arylated alkynes are synthesized from the corresponding aryl halides and terminal alkynes through Sonogashira type cross-coupling reactions through C(aryl)-C bond formation in the presence of a catalytic amount of N,N′-dibenzyl BINAM-CuI complex under mild reaction conditions. © 2009 Elsevier Ltd. All rights reserved.

An efficient copper(I) complex catalyzed Sonogashira type cross-coupling of aryl halides with terminal alkynes

A wide range of N-arylated indoles are selectively synthesized through intermolecular C(aryl)-N bond formation from the corresponding aryl iodides and indoles through Ullmann-type coupling reactions in the presence of a catalytic amount of easily available N,N,N′,N′-tetramethyl-BINAM-CuI complex under very mild reaction conditions. © 2009 Elsevier Ltd. All rights reserved.

Tetrahedron

An efficient, mild, and selective Ullmann-type N-arylation of indoles catalyzed by copper(I) complex

A DABCO-copper(I) chloride complex (5 mol%) together with TEMPO (5 mol%) in nitromethane as solvent has been used as an efficient catalytic system for the selective oxidation of benzylic and allylic alcohols into the corresponding carbonyl compounds at room temperature where molecular oxygen acts as an ultimate, stoichiometric oxidant and water is the only by-product. The solidstate structure determination of the DABCOcopper complex shows that the copper is in the + II oxidation state with trigonal bipyramidal geometry and exists in a linear polymeric structure due to strong hydrogen bonding. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

Advanced Synthesis and Catalysis

Aerobic, chemoselective oxidation of alcohols to carbonyl compounds catalyzed by a DABCO-copper complex under mild conditions

Sax's Dangerous Properties of Industrial Materials

p-Methoxybenzyl Alcohol 105-13-5

A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids

Journal of the American Chemical Society

Organic Solvent- and Halide-Free Oxidation of Alcohols with Aqueous Hydrogen Peroxide

Ruthenium tetraoxide catalyzed oxidation of nucleosides: A facile synthesis of 5′-carboxylic acid derivatives

CuCl catalyzed selective oxidation of primary alcohols to carboxylic acids with tert-butyl hydroperoxide at room temperature

Journal	Tetrahedron Letters
ISSN	00404039
Open Access	No