Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes

Dearomative cycloaddition reactions represent an ideal means of converting flat arenes into three-dimensional architectures of increasing interest in medicinal chemistry. Quinolines, isoquinolines, and quinazolines, despite containing latent diene and alkene subunits, are scarcely applied in cycload...

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Bibliographic Details
Published in:Science (American Association for the Advancement of Science) 2021-03, Vol.371 (6536), p.1338-1345
Main Authors: Ma, Jiajia, Chen, Shuming, Bellotti, Peter, Guo, Renyu, Schäfer, Felix, Heusler, Arne, Zhang, Xiaolong, Daniliuc, Constantin, Brown, M Kevin, Houk, Kendall N, Glorius, Frank
Format: Article
Language:English
Subjects:
Alkenes
Alkenes - chemistry
Aromatic compounds
Aromaticity
Atmospheric chemistry
Catalysis
Computer applications
Cycloaddition
Cycloaddition Reaction
Density functional theory
Diels-Alder reactions
Dienes
Energy Transfer
Hydrocarbons, Aromatic - chemistry
Iridium
Molecular Structure
Organic Chemistry
Organic compounds
Photochemicals
Quinolines
Quinolines - chemistry
Reactivity
Selectivity
Stereoisomerism
Stereoselectivity
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Summary:Dearomative cycloaddition reactions represent an ideal means of converting flat arenes into three-dimensional architectures of increasing interest in medicinal chemistry. Quinolines, isoquinolines, and quinazolines, despite containing latent diene and alkene subunits, are scarcely applied in cycloaddition reactions because of the inherent low reactivity of aromatic systems and selectivity challenges. Here, we disclose an energy transfer-mediated, highly regio- and diastereoselective intermolecular [4 + 2] dearomative cycloaddition reaction of these bicyclic azaarenes with a plethora of electronically diverse alkenes. This approach bypasses the general reactivity and selectivity issues, thereby providing various bridged polycycles that previously have been inaccessible or required elaborate synthetic efforts. Computational studies with density functional theory elucidate the mechanism and origins of the observed regio- and diastereoselectivities.
ISSN:0036-8075
1095-9203
DOI:10.1126/science.abg0720