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Dearomatization of Unactivated Arenes via Catalytic Hydroalkylation.

ABSTRACT: The dearomative cyclization of linear amides to complex spirocyclic butyrolactams has been enabled by photoredox catalysis through a reductive radical-polar crossover mechanism. This mechanism operates with precision on unactivated aromatic substrates to give a wide range of 1,4-hydroalkylation products. This method utilizes a simple organic catalyst/reductant pair to deliver products in a highly flexible manner with respect to substitution, and the products can be further functionalized under simple conditions to afford a collection of motifs. The mechanistic analysis performed here outlines the salient features of this strategy, which were applied to prepare a collection of complex scaffolds including the anticonvulsive agent gabapentin.

SUBMITTER: McDaniel KA

PROVIDER: S-EPMC8346228 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Dearomatization of Unactivated Arenes via Catalytic Hydroalkylation.

McDaniel Kelly A KA Blood Anna R AR Smith Gavin C GC Jui Nathan T NT

ACS catalysis 20210408 9

The dearomative cyclization of linear amides to complex spirocyclic butyrolactams has been enabled by photoredox catalysis through a reductive radical-polar crossover mechanism. This mechanism operates with precision on unactivated aromatic substrates to give a wide range of 1,4-hydroalkylation products. This method utilizes a simple organic catalyst/reductant pair to deliver products in a highly flexible manner with respect to substitution, and the products can be further functionalized under s ...[more]

PMID: 34367722

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