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

Authors

Renyu Guo
Souvik Adak
Peter Bellotti
Xinfeng Gao
W. Walker Smith
Sam Ngan Le
Jiajia Ma
K.N. Houk
Frank Glorius
Shuming Chen, Oberlin College
M. Kevin Brown

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.

Repository Citation

Guo, Renyu, Souvik Adak, Peter Bellotti, et al. 2022 "Photochemical Dearomative Cycloadditions of Quinolines and Alkenes: Scope and Mechanism Studies." Journal of the American Chemical Society 144(38): 17680-17691.

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