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Synthesis 2009(16): 2818-2824  
DOI: 10.1055/s-0029-1217406
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise Synthesis of ortho-Iodobenzyl Alcohols via Addition of ortho-Iodophenyl Grignard Reagent to Aldehydes and Ketones

Ján Cvengroš, Daniel Stolz, Antonio Togni*
Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich, Wolfgang-Pauli-Str. 10, 8093 Zurich, Switzerland
Fax: +41(44)6321310; e-Mail: togni@inorg.chem.ethz.ch;
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Publication History

Received 21 April 2009
Publication Date:
22 June 2009 (online)

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Abstract

A wide range of both secondary and tertiary ortho-iodobenzyl alcohols was synthesized via addition of ortho-iodophenyl ­Grignard reagents to aldehydes and ketones. Significant improvements in terms of yields were observed with ketones upon addition of CeCl3. The potential application of the target compounds as precursors for novel electrophilic trifluoromethylating reagents based on hyper-valent iodine derivatives was demonstrated.

Key words

addition reactions - Grignard reactions - organometallic reagents - benzyl alcohols - hypervalent iodine compounds

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