Title

Photochemical Dearomative Cycloadditions of Quinolines and Alkenes: Scope and Mechanism Studies

Abstract

Photochemical dearomative cycloaddition has emerged as a useful strategy to rapidly generate molecular complexity. Within this context, stereo- and regiocontrolled intermolecular para-cycloadditions are rare. Herein, a method to achieve photochemical cycloaddition of quinolines and alkenes is shown. Emphasis is placed on generating sterically congested products and reaction of highly substituted alkenes and allenes. In addition, the mechanistic details of the process are studied, which revealed a reversible radical addition and a selectivity-determining radical recombination. The regio- and stereochemical outcome of the reaction is also rationalized.

Publisher

American Chemical Society

Publication Date

9-15-2022

Document Type

Article

DOI

https://dx.doi.org/10.1021/jacs.2c07726

Keywords

Addition reactions, Cyclization, Hydrocarbons, Quinolines, Selectivity

Language

English

Format

text

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