Synthesis 2006(9): 1537-1541  
DOI: 10.1055/s-2006-926435
PAPER
© Georg Thieme Verlag Stuttgart · New York

α-Iodination of Ketones with MnO2/I2 Reagent Combination: A New Environmentally Friendly Procedure

Gaëlle Le Bras, Olivier Provot*, Alain Bekaert, Jean-François Peyrat, Mouâd Alami*, Jean-Daniel Brion
Laboratoire de Chimie Thérapeutique, BioCIS - CNRS (UMR 8076), Université Paris Sud XI, Faculté de Pharmacie, rue J. B. Clément, 92296 Châtenay-Malabry Cedex, France
Fax: +33(1)46835828; e-Mail: olivier.provot@cep.u-psud.fr; e-Mail: mouad.alami@cep.u-psud.fr;
Further Information

Publication History

Received 9 November 2005
Publication Date:
11 April 2006 (eFirst)

Abstract

In alcoholic media, α-iodination of ketones was accomplished using MnO2/I2 reagent combination in a new, environmentally friendly procedure. The reactions carried out under thermal conditions or microwave irradiation afforded α-iodo ketones in reasonable to good yields.

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15

We have observed that shorter reaction times (e.g., 1 h 30, 3 h 30 and 12 h) led to partial α-iodination of tetralones and after optimization, refluxing for 18 h led to better yields of iodo compounds.

16

Starting materials (ketones) and α-iodo ketones were easily separated by chromatography on silica gel.