![2,9-Dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione structure](https://static.chemtradehub.com/structs/308/3089-17-6-750b.webp "2,9-Dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione structure")
2,9-Dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione
CAS Number:
3089-17-6
Molecular Formula:
C20H10Cl2N2O2
One-pot generation of benzynes from 2-aminophenylboronates via a Rh(ii)-catalyzed N–H amination/oxidation/elimination cascade process
Literature Information
Publication Date
2019-11-18
DOI
10.1039/C9QO01115C
Impact Factor
5.281
Authors
Motoki Ito, Arisa Tanaka, Keiju Hatakeyama, Emi Kano, Kazuhiro Higuchi, Shigeo Sugiyama
View Original
Abstract
This article describes the first application of 2-aminophenylboronates as precursors for benzynes. Utilizing Rh2(HNCOCF3)4 as the catalyst, Rh(II)-nitrene-mediated N–H amination of the starting material triggered a cascade of oxidation/elimination processes resulting in the generation of benzynes, thus providing suitable conditions for a one-pot cycloaddition with azides or furans. The transformation proceeded under acid-, base-, and fluoride-free conditions, below ambient temperature, and was applicable to a range of substrates containing glycoside and nucleoside moieties, as well as silyl-functional groups.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Methyl-2-propanyl 4-iodo-1-piperidinecarboxylate
CAS Number:
301673-14-3
Molecular Formula:
C10H18INO2
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