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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.

SUBMITTER: Guo R

PROVIDER: S-EPMC9840784 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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

Guo Renyu R Adak Souvik S Bellotti Peter P Gao Xinfeng X Smith W Walker WW Le Sam Ngan SN Ma Jiajia J Houk K N KN Glorius Frank F Chen Shuming S Brown M Kevin MK

Journal of the American Chemical Society 20220915 38

Photochemical dearomative cycloaddition has emerged as a useful strategy to rapidly generate molecular complexity. Within this context, stereo- and regiocontrolled intermolecular <i>para</i>-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 re ...[more]

PMID: 36106902

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