Literature DB >> 16388643

Suzuki-Miyaura cross-coupling reactions of aryl tellurides with potassium aryltrifluoroborate salts.

Rodrigo Cella1, Rodrigo L O R Cunha, Ana E S Reis, Daniel C Pimenta, Clécio F Klitzke, Hélio A Stefani.   

Abstract

[reaction: see text] Palladium(0)-catalyzed cross-coupling between potassium aryltrifluoroborate salts and aryl tellurides proceeds readily to afford the desired biaryls in good to excellent yield. The reaction seems to be unaffected by the presence of electron-withdrawing or electron-donating substituents in both the potassium aryltrifluoroborate salts and aryl tellurides partners. Biaryls containing a variety of functional groups can be prepared. A chemoselectivity study was also carried out using aryl tellurides bearing halogen atoms in the same compound. In addition, this new version of the Suzuki-Miyaura cross-coupling reaction was monitored by electrospray ionization mass spectrometry where some reaction intermediates were detected and analyzed.

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Year:  2006        PMID: 16388643     DOI: 10.1021/jo052061r

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  7 in total

1.  Synthesis of functionalized organotrifluoroborates via the 1,3-dipolar cycloaddition of azides.

Authors:  Gary A Molander; Jungyeob Ham
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

2.  Linchpin synthons: metalation of aryl bromides bearing a potassium trifluoroborate moiety.

Authors:  Gary A Molander; Noel M Ellis
Journal:  J Org Chem       Date:  2006-09-15       Impact factor: 4.354

3.  Suzuki-Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-palladium complex catalyst.

Authors:  Guangming Nan; Fang Ren; Meiming Luo
Journal:  Beilstein J Org Chem       Date:  2010-06-28       Impact factor: 2.883

4.  2-(Dimethyl-amino-meth-yl)phenyl phenyl telluride.

Authors:  Tapash Chakraborty; Harkesh B Singh; Ray J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-09-26

5.  Copper-Catalyzed Synthesis of Unsymmetrical Diorganyl Chalcogenides (Te/Se/S) from Boronic Acids under Solvent-Free Conditions.

Authors:  Sumbal Saba; Giancarlo Vaccari Botteselle; Marcelo Godoi; Tiago Elias Allievi Frizon; Fábio Zazyki Galetto; Jamal Rafique; Antonio L Braga
Journal:  Molecules       Date:  2017-08-18       Impact factor: 4.411

6.  Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts.

Authors:  Hélio A Stefani; Rafael C Guadagnin; Artur F Keppler; Giancarlo V Botteselle; João V Comasseto; Carlos A Suganuma
Journal:  Beilstein J Org Chem       Date:  2008-02-05       Impact factor: 2.883

7.  Data on the catalytic mechanism of thiol peroxidase mimics.

Authors:  B Zadehvakili; N M Giles; J P Fawcett; G I Giles
Journal:  Data Brief       Date:  2016-05-24
  7 in total

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