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Synthesis of Substituted Benzaldehydes via a Two-Step, One-Pot Reduction/Cross-Coupling Procedure
Dorus Heijnen1, Hugo Helbert1,2, Gert Luurtsema2
1Stratingh Institute for Chemistry , University of Groningen , Nijenborgh 4 , 9747 AG Groningen , The Netherlands.
Abstract:
The synthesis of functionalized (benz)aldehydes, via a two-step, one-pot procedure, is presented. The method employs a stable aluminum hemiaminal as a tetrahedral intermediate, protecting a latent aldehyde, making it suitable for subsequent cross-coupling with (strong nucleophilic) organometallic reagents, leading to a variety of alkyl and aryl substituted benzaldehydes. This very fast methodology also facilitates the effective synthesis of a 11C radiolabeled aldehyde. Aluminum-ate complexes enable transmetalation of alkyl fragments onto palladium and subsequent cross-coupling.
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