ArticleThe Journal of organic chemistry2018
Synthesis of [3a,7a]-Dihydroindoles by a Tandem Arene Cyclopropanation/3,5-Sigmatropic Rearrangement Reaction.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
3 citing papers in PubMed.
- Asymmetric synthesis of complex tricyclo[3.2.2.0]nonenes from racemic norcaradienes: kinetic resolutionChemical science · 2023Article
- Modular Synthesis of Highly Substituted 3-Azapyrroles by Rh(II)-Catalyzed N-H Bond Insertion and Cyclodehydration.The Journal of organic chemistry · 2022Article
- Asymmetric Cyclopropanation with 4-Aryloxy-1-sulfonyl-1,2,3-triazoles: Expanding the Range of Rhodium-Stabilized Donor/Acceptor Carbenes to Systems with an Oxygen Donor Group.The Journal of organic chemistry · 2022Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Donor/acceptor carbenes provide a powerful platform for building molecular complexity, but the majority of their reactions have been limited to aryl and vinyl donor groups. We found that a N-containing donor/acceptor carbene precursor, 4-phthalimido- N-methanesulfonyl-1,2,3-triazole, reacts with unactivated arenes resulting in a mixture of [3+2]-cycloadducts, [3a,7a]-dihydroindoles, and formal C-H functionalization products in up to 82% yield upon heating. We also demonstrate that the formal C-H functionalization products arise from ring-opening of the [3+2]-cycloadducts. Computational studies suggest that the formal cycloaddition process takes places through a tandem arene cyclopropanation/6π electrocyclization/6π electrocyclic ring-opening/3,5-sigmatropic rearrangement reaction, which also accounts for the distinctive regioselectivity of the formal cycloaddition reaction.
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Registered trials
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