Literature DB >> 16235963

Palladium-catalyzed coupling reactions of bromothiophenes at the C-H bond adjacent to the sulfur atom with a new activator system, AgNO3/KF.

Kei Kobayashi1, Atsushi Sugie, Masabumi Takahashi, Kentaro Masui, Atsunori Mori.   

Abstract

[reaction: see text] Bromothiophene derivatives react with aryl iodides catalyzed by a palladium complex in the presence of a silver(I) nitrate/potassium fluoride system to induce coupling at the C-H bond, while the carbon-bromine bond is intact. The produced coupling product bearing the C-Br bond allows further palladium-catalyzed C-C bond-forming reactions in reasonable yields.

Entities:  

Year:  2005        PMID： 16235963     DOI： 10.1021/ol052063y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Mechanistic studies on direct arylation of pyridine N-oxide: evidence for cooperative catalysis between two distinct palladium centers.

Authors:  Yichen Tan; Fabiola Barrios-Landeros; John F Hartwig
Journal:  J Am Chem Soc       Date:  2012-02-17       Impact factor: 15.419

Review 2.  Direct transition metal-catalyzed functionalization of heteroaromatic compounds.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2007-03-05       Impact factor: 54.564

3.  Assessment of the intermediacy of arylpalladium carboxylate complexes in the direct arylation of benzene: evidence for C-H bond cleavage by "ligandless" species.

Authors:  Yichen Tan; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-02-11       Impact factor: 15.419

4.  Diarylthiophenes as inhibitors of the pore-forming protein perforin.

Authors:  Christian K Miller; Kristiina M Huttunen; William A Denny; Jagdish K Jaiswal; Annette Ciccone; Kylie A Browne; Joseph A Trapani; Julie A Spicer
Journal:  Bioorg Med Chem Lett       Date:  2015-12-07       Impact factor: 2.823

5.  Direct Arylation of Benzo[b]furan and Other Benzo-Fused Heterocycles.

Authors:  Toan Dao-Huy; Maximilian Haider; Fabian Glatz; Michael Schnürch; Marko D Mihovilovic
Journal:  European J Org Chem       Date:  2014-11-17

6.  Exploration of a series of 5-arylidene-2-thioxoimidazolidin-4-ones as inhibitors of the cytolytic protein perforin.

Authors:  Julie A Spicer; Gersande Lena; Dani M Lyons; Kristiina M Huttunen; Christian K Miller; Patrick D O'Connor; Matthew Bull; Nuala Helsby; Stephen M F Jamieson; William A Denny; Annette Ciccone; Kylie A Browne; Jamie A Lopez; Jesse Rudd-Schmidt; Ilia Voskoboinik; Joseph A Trapani
Journal:  J Med Chem       Date:  2013-11-19       Impact factor: 7.446

7.  Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group.

Authors:  Mariem Brahim; Hamed Ben Ammar; Jean-François Soulé; Henri Doucet
Journal:  Beilstein J Org Chem       Date:  2016-10-17       Impact factor: 2.883
  7 in total

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