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Synlett 2002(1): 0179-0180
DOI: 10.1055/s-2002-19347
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Diisobutylaluminun Hydride (DIBAL-H)

Isabel Fernández-Bachiller*
Instituto de Química Médica (CSIC), Juan de la Cierva, 3, 28006 Madrid, Spain
e-Mail: Lab310@iqm.csic.es;
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Publikationsdatum:
01. Februar 2007 (online)

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Introduction

Among reducing agents, diisobutylaluminun hydride (DIBAL-H) stands out, having been extensively used for a broad variety of reductive transformations in organic chemistry. It is easy to use and reduces many functional groups under mild reaction conditions. [1] Aldehydes, ketones, acids, esters, acid chlorides, amides, nitriles, isocyanates, nitro compounds, and disulfides are examples of suitable substrates, whereas alkyl halides are unreactive towards DIBAL-H. Usually, reactions are strongly solvent and/or temperature dependent and as an example, sulfides, sulfones, and sulfonic acids are unreactive in toluene at 0 ºC. [2]

Along with the reductive capability of DIBAL-H, its Lewis acid properties extend the scope of transformations, and the combination of these two properties has been used in the stereoselective synthesis of valuable products in chemistry, like pharmaceuticals. [3]

DIBAL-H is commercially available pure or in solution of alkanes, ethers, dichloromethane, toluene, etc.

Precautions: Neat DIBAL-H is a pyrophoric liquid and its solutions react violently with water, oxygen and related compounds. It is necessary to work in a fume hood, using anhydrous solvents, under inert atmosphere (argon or nitrogen).

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