Oxidative Homologation of Aldehydes to α-Ketoaldehydes by using Iodoform, o-Iodoxybenzoic Acid, and Dimethyl Sulf­oxide

An efficient three‐step synthetic route to α‐ketoaldehydes starting from aryl aldehydes is reported. The aldehydes were treated with iPrMgCl and iodoform to obtain β‐diiodoalcohols, which were then oxidized with o‐iodoxybenzoic acid at room temperature to the corresponding β‐diiodoketones. Subsequen...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2012, Vol.2012 (7), p.1439-1447
Main Authors: Zall, Andrea, Bensinger, Dennis, Schmidt, Boris
Format: Review
Language:English
Subjects:
Aldehydes
Homologation
Oxidation
Synthetic methods
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Summary:An efficient three‐step synthetic route to α‐ketoaldehydes starting from aryl aldehydes is reported. The aldehydes were treated with iPrMgCl and iodoform to obtain β‐diiodoalcohols, which were then oxidized with o‐iodoxybenzoic acid at room temperature to the corresponding β‐diiodoketones. Subsequent reaction of the β‐diiodoketone to the α‐ketoaldehyde occurred under oxygen transfer from dimethyl sulfoxide. These sensitive products were in situ cyclized with o‐phenylenediamine to form the stable monosubstituted quinoxalines, which could be characterized and isolated easily. α‐Ketoaldehydes are a versatile, highly reactive moiety for the synthesis of heterocyclic compounds. We investigated the transformation of aldehydes into α‐ketoaldehydes via β‐diiodoketone intermediates and finally applied the procedure to the synthesis of peptidic substrates.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201101835