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

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.