Transfer Hydrogenation of Ketones with (1-) as the Precatalyst

DOI: 10.1039/DT9930001191

Source and publish data:

Journal of the Chemical Society, Dalton Transactions p. 1191 - 1200 (1993)

Update date:2022-09-26

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Authors:

Bhaduri, Sumit

Sharma, Krishna

Mukesh, Doble

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Article abstract of DOI:10.1039/DT9930001191

The cluster 1a has been found to be an efficient precatalyst for the transfer hydrogenations of ketones and α,β-unsaturated ketones.With substrates such as (5S)-carvone <2-methyl-5-(1-methylethenyl)cyclohex-2-en-1-one>, (3R)-methylcyclopentanone and (3R)-methylcyclohexanone, moderate to high diastereoselectivities were observed for reduction of the conjugated olefinic and ketonic functionalities respectively.Aromatisation of carvone to 5-isopropyl-2-methylphenol and disproportionation of cyclohex-2-en-1-one to phenol and cyclohexanone have also been found to be catalysed by 1a.Studies with radical inhibitors and other evidence suggest a radical mechanism for the transfer-hydrogenation and aromatisation reactions.In the transfer hydrogenation of cyclohex-2-en-1-one, the rate of conversion of 1a into other soluble species can be modelled accurately if autocatalysis is assumed.The time-dependent concentration profiles of cyclohex-2-en-1-one, cyclohexanone and cyclohexanol are simulated well if autocatalytic formation of an active intermediate followed by consecutive reactions leading to the formation of products is assumed.Such a model is also consistent with the proposed radical mechanism.

Full text of DOI:10.1039/DT9930001191

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