A wide range of primary and secondary multifunctional alcohols, α-hydroxyamides, and α-hydroxyesters were oxidized to their corresponding aldehydes, ketones, α-ketoamides, and α-ketoesters under mild reaction conditions using 2,2,6,6-tetramethylpiperidine-1-oxyl as a catalyst with calcium hypochlorite as an oxidant [TEMPO-Ca(OCl) 2]. This simplified method does not require any transition metals, acids, or bases and demonstrates controlled and selective oxidation of structurally diverse alcohols, affording moderate to excellent yields at room temperature. © 2012 Taylor &amp; Francis Group, LLC.

Anju Chadha

Department Of Biotechnology

acid

alcohol

aldehyde

amide

base

ester

HYPOCHLORITE

ketone

Metal

article

catalysis

chemical reaction

oxidation

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

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IIT Madras

Simplified Procedure for TEMPO-Catalyzed Oxidation: Selective Oxidation of Alcohols, α-Hydroxy Esters, and Amides Using TEMPO and Calcium Hypochlorite

Synthetic Communications

Optically pure allylic alcohols and 4-phenylbutan-2-ols were prepared by oxidative kinetic resolution using whole cells of Candida parapsilosis ATCC 7330. Only the 'S' enantiomer is selectively oxidized to the corresponding keto compound (yield, 37-46%) leaving the 'R' alcohol (yield, 37-52% and ee 46 to >99%). The biocatalytic method is carried out under mild conditions at 20°C, pH 6.5 in phosphate buffer. © 2014 The Royal Society of Chemistry.

RSC Advances

Enantioselective oxidation of secondary alcohols by Candida parapsilosis ATCC 7330

Oxidation of propargylic alcohols to the corresponding aldehydes and ketones was achieved at room temperature using 2,2,6,6-tetramethylpiperidine-1- oxyl (TEMPO) and calcium hypochlorite (Ca(OCl)2). Propargylic diols yielded corresponding dialdehydes as the product. This system was found to be very efficient for both the electron donating and electron withdrawing groups such as methoxy and nitro substituted alcohols, respectively. This method does not require any additives and demonstrates the controlled, selective oxidation of propargylic alcohols affording up to 97% isolated yield. © The Royal Society of Chemistry 2013.

A simple and efficient method for mild and selective oxidation of propargylic alcohols using TEMPO and calcium hypochlorite

Biocatalytic reduction of primary and secondary α-keto amides was accomplished using whole cells of Candida parapsilosis ATCC 7330. The primary (R)-α-hydroxy amides were obtained in good enantiomeric excess (up to 94%) and conversion (88-99%) as compared to the secondary (R)-α-hydroxy amides. © 2012 Elsevier B.V.

Catalysis Today

Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330

An efficient protocol for the synthesis of a variety of <a href="https://www.sciencedirect.com/topics/chemical-engineering/azobenzene">azobenzenes</a> and <a href="https://www.sciencedirect.com/topics/chemical-engineering/hydrazine">hydrazines</a> from aromatic <a href="https://www.sciencedirect.com/topics/chemical-engineering/amine">amines</a> under mild reaction conditions is developed using Cu(I) catalyst. The copper cataylst used in this study comprises of CuBr, DMAP and AIBN. The plausible proposed mechanism for this dehydrogenative homo coupling of aromatic amines is depicted.

Catalysis Communications

Cu(I) catalyzed dehydrogenative homo coupling of aromatic amines under simple and mild reaction conditions

ChemInform

ChemInform Abstract: Simplified Procedure for TEMPO-Catalyzed Oxidation: Selective Oxidation of Alcohols, α-Hydroxy Esters, and Amides Using TEMPO and Calcium Hypochlorite.

Recueil des Travaux Chimiques des Pays-Bas

Oxydation de sulfure en sulfoxyde par l'hypochlorite de calcium et le chlorite de sodium: Optimisation des conditions opératoires par la méthode des plans d'expériences

Proceedings of the National Academy of Sciences

Chiral N-salicylidene vanadyl carboxylate-catalyzed enantioselective aerobic oxidation of -hydroxy esters and amides

Tetrahedron Letters

Oxidation of tartronic acid and dihydroxyacetone to sodium mesoxalate mediated by TEMPO

Angewandte Chemie

Effiziente kupferkatalysierte aerobe Oxidation primärer Alkohole

Simplified procedure for TEMPO-catalyzed oxidation: Selective oxidation of alcohols, α-hydroxy esters, and amides using TEMPO and calcium hypochlorite

Journal	Synthetic Communications
ISSN	00397911
Open Access	No