Palladium(II)-Catalyzed C(sp3)–H Activation of N,O-Ketals towards a Method for the β-Functionalization of Ketones

Abstract A method for the formal β-functionalization of aliphatic ketones via a palladium-catalyzed sp 3 C–H activation pathway is reported. An N,O-ketal directs an aliphatic C–H carbonylation to form γ-lactams which upon hydrolysis generate γ-keto carboxylic acids. This C–C bond-forming reaction is...

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Bibliographic Details
Published in:Synlett 2019-03, Vol.30 (4), p.454-458
Main Authors: Ho, Danny K. H., Calleja, Jonas, Gaunt, Matthew J.
Format: Article
Language:English
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Summary:Abstract A method for the formal β-functionalization of aliphatic ketones via a palladium-catalyzed sp 3 C–H activation pathway is reported. An N,O-ketal directs an aliphatic C–H carbonylation to form γ-lactams which upon hydrolysis generate γ-keto carboxylic acids. This C–C bond-forming reaction is tolerant of a range of functional groups, enabling the synthesis of a range of synthetically important building blocks. Furthermore, the concepts underlying this transformation have also enabled the development of a related C–H alkenylation process to highly functionalised heterocycles.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1611664