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

Photochemical dearomative cyclo addition 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.

Automated summary

Photochemical dearomative cycloaddition is a useful strategy for rapidly generating molecular complexity, and intermolecular para-cycloadditions with stereo- and regiocontrol are rare. In this study, a method for achieving photochemical cycloaddition of quinolines and alkenes is presented, with an emphasis on generating sterically congested products and reacting highly substituted alkenes and allenes. The mechanistic details of the process, including reversible radical addition and selectivity-determining radical recombination, are investigated. The regio- and stereochemical outcome of the reaction is also rationalized.