Literature DB >> 32495480

"Phenalenannulations: Three-Point Double Annulation Reactions that Convert Benzenes into Pyrenes".

Rahul Kisan Kawade1, Chaowei Hu2, Nikolas R Dos Santos2, Noelle Watson2, Xinsong Lin3, Kenneth Hanson4, Igor Alabugin5.   

Abstract

"3-Point annulations", or ''phenalenannulations" transform a benzene ring directly into a substituted pyrene by "wrapping" two new cycles around the perimeter of the central ring at three consecutive carbon atoms. This efficient, modular, and general method for p-extension opens access to non- symmetric pyrenes and their expanded analogues. Potentially, this approach can convert any aromatic ring bearing a -CH 2 Br or a -CHO group into a pyrene moiety.  Depending upon the workup choices, the process can be directed towards either tin- or iodo-substituted product formation, giving complementary choices for further various cross-coupling reactions. The two-directional bis-double annulation adds two new polyaromatic extensions with a total of six new aromatic rings at a central core.
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Annulation; Radical; alkyne; arenes; pyrenes

Year:  2020        PMID: 32495480     DOI: 10.1002/anie.202006087

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  2 in total

1.  Cascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids.

Authors:  Sergey Francevich Vasilevsky; Ol'ga Leonidovna Krivenko; Irina Vasilievna Sorokina; Dmitry Sergeevich Baev; Tatyana Genrikhovna Tolstikova; Igor V Alabugin
Journal:  Molecules       Date:  2021-11-15       Impact factor: 4.411

2.  Acenaphthenoannulation Induced by the Dual Lewis Acidity of Alumina.

Authors:  Vladimir Akhmetov; Mikhail Feofanov; Cordula Ruppenstein; Josefine Lange; Dmitry Sharapa; Marjan Krstić; Frank Hampel; Evgeny A Kataev; Konstantin Amsharov
Journal:  Chemistry       Date:  2022-04-26       Impact factor: 5.020

  2 in total

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