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

Govindasamy Sekar

Department Of Chemistry

Madithedu Muneeswara

Nallappan Sundaravelu

1 (2 METHYL)PHENYL 2 TOSYLPROPAN 1 ONE

1 (3 FLUORO)PHENYL 2 TOSYLPROPAN 1 ONE

1 (3 TRIFLUOROMETHYL)PHENYL 2 TOSYLPROPAN 1 ONE

benzyl alcohol

BETA KETO SULFONE DERIVATIVE

N bromosuccinimide

SODIUM ARENESULFINATE

SULFINIC ACID DERIVATIVE

sulfone derivative

unclassified drug

article

bromination

chemical reaction

controlled study

drug structure

drug synthesis

nucleophilicity

oxidation

priority journal

Sulfonylation

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

A transition-metal-free oxidative amination of secondary benzyl alcohols has been developed using N-bromosuccinimide as the oxidant and source of succinimide. The control experiments revealed that the transformation underwent via oxidation of alcohol to ketone, α-bromination of ketone and diazabicyclo[5.4.1]undec-7-ene (DBU) base-mediated nucleophilic substitution of the by-product succinimide. Various substituted benzyl alcohols and N-bromoimides were examined to form α-imido ketones in short reaction timespans. The protocol was successfully extended to a gram scale reaction. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ChemistrySelect

Dual Role of N-Bromosuccinimide as Oxidant and Succinimide Surrogate in Domino One-Pot Oxidative Amination of Benzyl Alcohols for the Synthesis of α–Imido Ketones

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.

Chemical Communications

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

A metal-free one-pot strategy has been developed for the first time to synthesize pharmaceutically important α-amino ketones from readily available benzylic secondary alcohols and amines using N-bromosuccinimide. This new reaction proceeds via three consecutive steps involving oxidation of alcohols, α-bromination of ketones, and nucleophilic substitution of α-bromo ketones to give α-amino ketones. Importantly, this novel one-pot greener reaction avoids direct usage of toxic and corrosive bromine. This methodology has been employed efficiently to synthesize pharmaceutically important amfepramone and pyrovalerone in a single step. © 2015 American Chemical Society.

Organic Letters

A versatile and one-pot strategy to synthesize α-amino ketones from benzylic secondary alcohols using N -bromosuccinimide

Tetrahedron Letters

Efficient sulfonylation of ketones with sodium sulfinates for the synthesis of β-keto sulfones

Chemistry - An Asian Journal

Synthesis of β-Keto Sulfones by a Catalyst-Free Reaction of Aryldiazonium Tetrafluoroborates, Sulfur Dioxide, and Silyl Enol Ethers

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

Journal	Data powered by TypesetTetrahedron
Publisher	Data powered by TypesetElsevier Ltd
ISSN	00404020
Open Access	No