Visible light mediated photocatalytic [2 + 2] cycloaddition/ring-opening rearomatization cascade of electron-deficient azaarenes and vinylarenes
Entity
UAM. Departamento de Química Inorgánica; UAM. Departamento de Química OrgánicaPublisher
Nature ResearchDate
2020-12-01Citation
Communications Chemistry 3.1 (2020): 132ISSN
2399-3669 (online)Funded by
We acknowledge the financial support from the Spanish Government (RTI2018–095038-B-I00), CAM_UAM (SI1/PJI/2019-00237), CCC-UAM (computing time), and ERC (ERC-CG, 647550). The authors also wish to thank the ‘Comunidad de Madrid’ and European Structural Funds for their financial support to FotoArt-CM project (S2018/NMT-4367)Project
Gobierno de España. RTI2018-095038-B-I00; info:eu-repo/grantAgreement/EC/H2020/647550/EU//UNBICATEditor's Version
https://doi.org/10.1038/s42004-020-00378-xSubjects
Alkene; Cross-Coupling Reactions; Photocatalysis; QuímicaRights
© 2020 The Author(s)Abstract
The broad presence of azaarene moieties in natural products has promoted the development of new functionalization reactions, giving access to larger libraries of bioactive compounds. The light promoted [2+ 2] photocycloaddition reaction to generate cyclobutanes has been extensively studied in photochemistry. In particular, De Mayo reported the [2 + 2] cycloaddition followed by retroaldol condensation between enols of 1,3-dicarbonyls and double bonds to synthesize 1,5-dicarbonyls. Herein, we describe the [2 + 2] photocycloaddition followed by a ring-opening rearomatization reaction between electron-deficient 2-methylene-azaarenes and double bonds, taking advantage of the ability of these heterocyclic derivatives to form the corresponding pseudo-enamine intermediate. The procedure
shows a high functional group tolerance either on the double bond or the heteroarene side and allows the presence of different electron-withdrawing groups. In addition, the wide applicability of this reaction has been demonstrated through the late-stage derivatization of several natural products. Photochemical studies, together with theoretical calculations, support a mechanism involving the photosensitization of the pseudo-enamine intermediate
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Google Scholar:Salaverri Mora, Noelia
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Mas Ballesté, Rubén
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Marzo Puerta, Leyre
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Alemán Lara, José Julián
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