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Reductive Coupling of Aromatic Aldehydes Promoted by an Aqueous TiCl3/tBuOOH System in Alcoholic Cosolvents

✍ Scribed by Angelo Clerici; Cosimina Greco; Walter Panzeri; Nadia Pastori; Carlo Punta; Ombretta Porta

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 130 KB
Volume: 2007
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200700252

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✦ Synopsis

Abstract

The tert‐butoxyl radical, generated by the aqueous Ti^III^/TBHP system, abstracts an H atom from alcoholic cosolvents (EtOH, __i__PrOH), leading to α‐hydroxyalkyl radicals thatreduce aromatic aldehydes to the corresponding 1,2‐diols. The reactivities observed are explained by resonance stabilization of the α‐hydroxybenzyl radicals formed in the electron‐transfer (ET) process. Good Hammett‐type correlations are obtained. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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