Visible-light induced generation of bifunctional nitrogen-centered radicals: a concise synthetic strategy to construct bicyclo[3.2.1] octane and azepane cores

A photocatalytic tandem cyclization of o -alkenylbenzaldehydes using pyridinium salts as the amination reagent is described. A variety of valuable seven-membered nitrogenous heterocyclic skeletons are prepared in modest to excellent yields in concise one-step. This transformation features mild react...

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Bibliographic Details
Published in:Science China. Chemistry 2021-02, Vol.64 (2), p.274-280
Main Authors: Yu, Wan-Lei, Jiang, Hao-Wen, Yan, Lei, Feng, Zhi-Tao, Luo, Yong-Chun, Xu, Peng-Fei
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Density functional theory
Functional groups
Investigations
Light
Nitrogen
Photocatalysis
Reagents
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Summary:A photocatalytic tandem cyclization of o -alkenylbenzaldehydes using pyridinium salts as the amination reagent is described. A variety of valuable seven-membered nitrogenous heterocyclic skeletons are prepared in modest to excellent yields in concise one-step. This transformation features mild reaction conditions and exceptional functional group tolerance. In addition, combining control experiments and density functional theory (DFT) calculations on the mechanism can explain the reaction selectivity.
ISSN:1674-7291
1869-1870
DOI:10.1007/s11426-020-9852-8