Abstract
The transfer dehydrogenation of several ketones by (PCP)IrH 2 (PCP = κ 3-C 6H 3-2,6-(CH 2P tBu 2) 2) ( 1) has been observed. Catalytic turnover was inhibited in most cases by the formation of stable metallacycles or the O–H oxidative addition of phenolic products. Catalytic transfer dehydrogenation of 3,3-dimethylcyclohexanone was achieved, giving the corresponding α,β-enone. The transfer dehydrogenation reaction of cycloheptanone with 1 was found to generate a surprisingly stable PCP-iridium troponyl hydride ( 9), which is stabilized by conjugation and possibly represents an unusual bicyclo[5.2.0]troponyliridium metalloaromatic structure. Complex 9 was found to catalyze the dimerization of tropone to give a fused tricyclic dihydrodicycloheptafuranol. A mechanism for this reaction is proposed wherein the coordinated troponyl group nucleophilically attacks a free tropone molecule.
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