Literature DB >> 28093829

Unprecedented Access to β-Arylated Selenophenes through Palladium-Catalysed Direct Arylation.

Aymen Skhiri1,2, Ridha Ben Salem2, Jean-François Soulé1, Henri Doucet1.   

Abstract

Several reported methods allow access to α-arylated selenophenes, whereas the synthesis of β-arylated selenophenes remains very challenging. Here, the Pd-catalysed coupling of benzenesulfonyl chlorides with selenophenes affording regiospecific β-arylated selenophenes is reported. The reaction proceeds with easily accessible catalyst, base and substrates, and tolerates a variety of substituents both on the benzene and selenophene moieties. This transformation allows the programmed synthesis of polyarylated selenophenes with potential applications in pharmaceutical and materials chemistry, as the installation of aryl groups at the desired positions can be achieved.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H functionalization; benzenesulfonyl chlorides; homogeneous catalysis; palladium; selenophenes

Year:  2017        PMID: 28093829     DOI: 10.1002/chem.201700202

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  3 in total

Review 1.  Recent Advances in the Synthesis of Selenophenes and Their Derivatives.

Authors:  Paola S Hellwig; Thiago J Peglow; Filipe Penteado; Luana Bagnoli; Gelson Perin; Eder J Lenardão
Journal:  Molecules       Date:  2020-12-13       Impact factor: 4.411

2.  Reactivity of bromoselenophenes in palladium-catalyzed direct arylations.

Authors:  Aymen Skhiri; Ridha Ben Salem; Jean-François Soulé; Henri Doucet
Journal:  Beilstein J Org Chem       Date:  2017-12-22       Impact factor: 2.883

3.  Synthesis of 3,4-Bis(Butylselanyl)Selenophenes and 4-Alkoxyselenophenes Promoted by Oxone®.

Authors:  Paola S Hellwig; Jonatan S Guedes; Angelita M Barcellos; Gelson Perin; Eder J Lenardão
Journal:  Molecules       Date:  2021-04-19       Impact factor: 4.411

  3 in total

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