Reactions of Ketones Containing a Directing Group

This rhodium-mediated C-C=0 activation was also used in the catalytic conversion of 8-quinolinyl ketones bearing a hydrogen at Cp, such as 8, into 

An intermolecular version of this carboacylation reaction was developed by the same group, using a strained bicyclic alkene [13]. When 8-quinolinyl 

It is proposed that the cleaved methyl or phenyl group in 21 is coupled with arylboronic acid via intermediate 24, and is released as a methyl- or phenyl-arene, respectively. The resultant acylrhodium 25 is then oxidized to 26 by the action of Cul and O2 to undergo additional transmetalation from arylboronic acid. In accordance with the proposed mechanism, the reaction did not proceed at all under a nitrogen atmosphere. 

A 2-phenylpyridine system was used in the rhodium-catalyzed decarbonyla-tion reaction of ketones (Eq. (6.7)) [16]. Unlike the reaction shown in Eq. (6.6), P hydrogen is not available for intermediate 33, and this alters the course of the reaction to decarbonylation. 

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