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Issue 3, 2012
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Direct aerobic α,β-dehydrogenation of aldehydes and ketones with a Pd(TFA)2/4,5-diazafluorenone catalyst

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Abstract

The direct α,β-dehydrogenation of aldehydes and ketones represents an efficient alternative to stepwise methods to prepare enal and enone products. Here, we describe a new Pd(TFA)2/4,5-diazafluorenone dehydrogenation catalyst that overcomes key limitations of previous catalyst systems. The scope includes successful reactivity with pharmaceutically important cyclopentanone and flavanone substrates, as well as acyclic ketones. Preliminary mechanistic studies compare the reactivity of this catalyst to previously reported dehydrogenation catalysts and reveal that cleavage of the α-C–H bond of the ketone is the turnover-limiting step of the catalytic mechanism.

Graphical abstract: Direct aerobic α,β-dehydrogenation of aldehydes and ketones with a Pd(TFA)2/4,5-diazafluorenone catalyst

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Publication details

The article was received on 26 Sep 2011, accepted on 31 Oct 2011 and first published on 31 Oct 2011


Article type: Edge Article
DOI: 10.1039/C1SC00724F
Citation: Chem. Sci., 2012,3, 887-891
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    Direct aerobic α,β-dehydrogenation of aldehydes and ketones with a Pd(TFA)2/4,5-diazafluorenone catalyst

    T. Diao, T. J. Wadzinski and S. S. Stahl, Chem. Sci., 2012, 3, 887
    DOI: 10.1039/C1SC00724F

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