A domino synthesis of α-hydroxy ketones has been developed from benzylic secondary alcohols employing catalytic iodonium ions stabilized by DMSO. The reaction proceeds through an unprecedented sequential oxidation of alcohols to ketone and its α-hydroxylation in a controlled manner. The spectroscopic evidence establishes the possibility of formation of a stable halogen-bonded adduct between DMSO and iodonium ions. © 2017 The Royal Society of Chemistry.

Govindasamy Sekar

Department Of Chemistry

Somraj Guha

Imran Kazi

Pranamita Mukherjee

alcohol derivative

Dimethyl Sulfoxide

halogen

Iodine

ketone derivative

article

catalysis

catalyst

chemical bond

hydrogen bond

molecular stability

oxidation

quantum yield

reaction analysis

Stereoselectivity

stereospecificity

synthesis

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

Chemical Communications

An efficient synthetic route towards the synthesis of β-keto sulfones has been developed from secondary benzyl alcohols using N-bromosuccinimide (NBS). The present protocol utilizes NBS as oxidant as well as brominating agent, readily accessible benzyl alcohols and sodium arenesulfinates as the sulfonylating reagent under mild conditions. The control experiments revealed that the reaction proceeds via oxidation of alcohol to ketone, α-bromination of ketone and nucleophilic substitution by sodium arenesulfinate. Furthermore, the efficiency of the methodology was tested with a gram scale reaction and also shown the synthetic utility. © 2019

Tetrahedron

NBS-mediated synthesis of β-keto sulfones from benzyl alcohols and sodium arenesulfinates

An efficient metal-free methodology for the synthesis of α-ketoesters has been developed using α-hydroxy ketones and alcohols which follows domino alcohol oxidation and esterification reaction sequence. This methodology shows wide range of substrate scopes to bestow the products in excellent yield. A gram scale synthesis has been carried out to show the practical utility of the protocol. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ChemistrySelect

Domino Oxidative Esterification of 2-Oxo Alcohol Using 2-Iodoxybenzoic Acid/I2: A Route to Synthesize α-Ketoester

RSC Adv.

Direct synthesis of α-hydroxyacetophenones through molecular iodine activation of carbon–carbon double bonds

Chem. Sci.

A solvent-resistant halogen bond

Chemical Society Reviews

Halogen bonding in solution

Alcohols

Direct Addition of Alkyl- and Arylmagnesium Halides

Enzyme encapsulation in nanoporous silica spheresElectronic supplementary information (ESI) available: experimental details, and details of particle characterization. See http://www.rsc.org/suppdata/cc/b4/b403871a/

Halogen-bonded iodonium ion catalysis: A route to α-hydroxy ketones: Via domino oxidations of secondary alcohols and aliphatic C-H bonds with high selectivity and control

Journal	Data powered by TypesetChemical Communications
Publisher	Data powered by TypesetRoyal Society of Chemistry
ISSN	13597345
Open Access	No