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Issue 79, 2017
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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

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Abstract

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.

Graphical abstract: 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

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Article information


Submitted
22 Jul 2017
Accepted
14 Sep 2017
First published
14 Sep 2017

Chem. Commun., 2017,53, 10942-10945
Article type
Communication

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

S. Guha, I. Kazi, P. Mukherjee and G. Sekar, Chem. Commun., 2017, 53, 10942
DOI: 10.1039/C7CC05697D

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