Work

Dearomatization of Unactivated Arenes via Catalytic Hydroalkylation

Year: 2021

Type: article

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.

Source: ACS Catalysis

DOI: 10.1021/acscatal.1c00732

Authors: Kelly A. McDaniel, Anna R. Blood, Gavin C. Smith, Nathan T. Jui

Institutions: Emory University, Winship Cancer Institute

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Novel Radical Reactions for C-C Bond Formation, G911242656