ArticleCommunications chemistry2020
Visible light mediated photocatalytic [2 + 2] cycloaddition/ring-opening rearomatization cascade of electron-deficient azaarenes and vinylarenes.
Article in Communications chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Regiospecific de mayo reactions of enamino ketones.Nature communications · 2026Article
- Reenvisioning the De Mayo Reaction: A Boron-Enabled Cycloaddition Approach.Angewandte Chemie (International ed. in English) · 2026Article
- Chiral hafnium phosphate catalyzed asymmetric de Mayo reaction via visible-light-induced dearomatization.Nature communications · 2026Article
- Charge-recombinative triplet sensitization of alkenes for DeMayo-type [2 + 2] cycloaddition.Chemical science · 2024Article
- Asymmetric photoredox catalytic formal de Mayo reaction enabled by sensitization-initiated electron transfer.Nature chemistry · 2024Article
- Recent Visible Light and Metal Free Strategies in [2+2] and [4+2] Photocycloadditions.European journal of organic chemistry · 2021Review
Corrections and comments
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
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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Registered trials
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