Literature DB >> 31121079

Gold-catalyzed [4+2] Annulations of Dienes with Nitrosoarenes as 4 π Donors: Nitroso-Povarov Reactions.

Ching-Nung Chen1, Rai-Shung Liu1.   

Abstract

This work reports the first success of the nitroso-Povarov reaction, involving gold-catalyzed [4+2] annulations of nitrsoarenes with substituted cyclopentadienes. In this catalytic sequence, nitrosoarenes presumably attack gold-π-dienes by a 1,4-addition pathway, generating allylgold nitrosonium intermediates to complete an intramolecular cyclization. Acyclic dienes are also applicable substrates, and affording oxidative nitroso-Povarov products.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Povarov reactions; annulations; dienes; gold; heterocycles

Year:  2019        PMID： 31121079     DOI： 10.1002/anie.201903615

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


  6 in total

Review 1.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

2.  Gold-Catalyzed Reaction of Propargyl Esters and Alkynylsilanes: Synthesis of Vinylallene Derivatives through a Twofold 1,2-Rearrangement.

Authors:  Olaya Bernardo; Silvia González-Pelayo; Israel Fernández; Luis A López
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-21       Impact factor: 16.823

3.  Gold-Catalyzed Hydroalkoxylation/Povarov Reaction Cascade of Alkynols with N-Aryl Imines: Synthesis of Tetrahydroquinolines.

Authors:  Ciwang He; Ju Cai; Yang Zheng; Chao Pei; Lihua Qiu; Xinfang Xu
Journal:  ACS Omega       Date:  2019-09-09

4.  Gold(I)-Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates.

Authors:  Luke O'Brien; Stephen P Argent; Kristaps Ermanis; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-25       Impact factor: 16.823

5.  Gold-Catalyzed Regioselective Synthesis of Crowded Cyclopentadienes by Migratory Cycloisomerization of Vinylallenes.

Authors:  Olaya Bernardo; Javier González; Javier Borge; Luis A López
Journal:  Org Lett       Date:  2022-07-12       Impact factor: 6.072

6.  Sc(OTf)3-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction.

Authors:  Xabier Jiménez-Aberásturi; Francisco Palacios; Jesús M de Los Santos
Journal:  J Org Chem       Date:  2022-08-16       Impact factor: 4.198
  6 in total

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