Work

Dearomatization through Photoredox Hydroarylation: Discovery of a Radical-Polar Crossover Strategy

Year: 2021

Type: article

Abstract: Indole dearomatization has been achieved via radical hydroarylation. Under mild photoredox conditions, a range of indole derivatives undergo hydroarylation to form 2-arylindoline products. Mechanistically, radical termination occurs primarily via stepwise reduction/protonation, with a small contribution from concerted hydrogen atom transfer. This mechanistic understanding prompted the extension of this reactivity to benzenoid dearomatization. This work formed the foundation of our program, which utilizes reductive radical-polar crossover to drive highly selective dearomatization pathways.

Source: Organic Letters

DOI: 10.1021/acs.orglett.1c02006

Authors: Kelly A. McDaniel, Nathan T. Jui

Institution: Emory University

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: G3094633945, Novel Radical Reactions for C-C Bond Formation