A mild and efficient, ionic-liquid-assisted green protocol for the chemoselective oxygenation of benzylic C-H bonds to corresponding ketones using ionic liquid [bmim]Br with tert-butyl hydroperoxide has been developed. The method reported in this paper has the advantages of [bmim]Br acting as recyclable solvent and reagent. The usage of additives such as acids or bases and metal salts is not required. The developed strategy is further extended to oxidation of secondary alcohols to respective ketones under similar optimized reaction conditions.

Rajasekhara Reddy Sabbasani

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Naidu S

Vellore Institute of Technology (VIT) is a private university located in&nbsp;Tamil Nadu, India. Founded in 1984, as Vellore Engineering College, the institution offers 20 undergraduate, 34 postgraduate, four integrated and four research programs. It has campuses in Vellore, Amravati, Bhopal and Chennai.

VIT is one of the top ranked private universities in India according to NIRF, THE and QS Rankings.&nbsp;Govt. of India has recognized&nbsp;VIT, Vellore as an&nbsp;Institution of Eminence. This has allowed VIT to take independent quality initiatives and move up in world ranking.

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VIT University

Journal of Molecular Liquids

Catalytic oxidation reactions often suffer from drawbacks such as low yields and poor selectivity. Particularly, selective oxidation of alcohols becomes more difficult when a compound contains more than one oxidizable functional group. In order to deliver a methodology that addresses these issues, herein we report an efficient, aerobic, chemoselective and simplified approach to oxidize a broad range of benzyl and propargyl alcohols containing diverse functional groups to their corresponding aldehydes and ketones in excellent yields under mild reaction conditions. Optimal yields were obtained at room temperature using 1 mmol substrate, 10 mol % copper(I) iodide, 10 mol % 4-dimethylaminopyridine (DMAP), and 1 mol % 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) in acetonitrile, under an oxygen balloon. The catalytic system can be applied even when sensitive and oxidizable groups such as alkynes, amines, and phenols are present; starting materials and products containing such groups were found to be stable under the developed conditions.

Fulltext

ChemistryOpen

Chemoselective Oxidation of Benzyl, Amino, and Propargyl Alcohols to Aldehydes and Ketones under Mild Reaction Conditions

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

The Journal of Organic Chemistry

Metal-Free Oxidative Ipso-Carboacylation of Alkynes: Synthesis of 3-Acylspiro[4,5]trienones from N-Arylpropiolamides and Aldehydes

Organic Chemistry Frontiers

Copper-catalyzed oxidative ipso-carboalkylation of activated alkynes with ethers leading to 3-etherified azaspiro[4.5]trienones

Green Chemistry

Metal-free allylic/benzylic oxidation strategies with molecular oxygen: recent advances and future prospects

Ionic liquid [bmim]Br assisted chemoselective benzylic C H oxidations using -butyl hydroperoxide

Journal	Data powered by TypesetJournal of Molecular Liquids
Publisher	Data powered by TypesetElsevier BV
ISSN	0167-7322
Open Access	0