Literature DB >> 21192652

Palladium-catalyzed indole, pyrrole, and furan arylation by aryl chlorides.

Enrico T Nadres1, Anna Lazareva, Olafs Daugulis.   

Abstract

The palladium-catalyzed n class="Chemical">direct arylation of indoles, pyrroles, and furans by aryl chlorides has been demonstrated. The method employs a palladium acetate catalyst, 2-(dicyclohexylphosphino)-biphenyl ligand, and an inorganic base. Electron-rich and electron-poor aryl chlorides as well as chloropyridine coupling partners can be used, and arylated heterocycles are obtained in moderate to good yields. Optimization of base, ligand, and solvent is required for achieving best results.

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Year:  2010        PMID: 21192652      PMCID: PMC3021639          DOI: 10.1021/jo1018969

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


  62 in total

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Authors:  Benjamin S Lane; Dalibor Sames
Journal:  Org Lett       Date:  2004-08-19       Impact factor: 6.005

2.  Rational ligand design in constructing efficient catalyst systems for Suzuki-Miyaura coupling.

Authors:  Masahiro Miura
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-19       Impact factor: 15.336

3.  Synthesis of self-organizing mesogenic materials containing a sulfur-based five-membered heterocyclic core.

Authors:  Alexander Seed
Journal:  Chem Soc Rev       Date:  2007-07-02       Impact factor: 54.564

4.  Regioselective palladium-catalyzed arylation of 2-furaldehyde.

Authors:  M S McClure; B Glover; E McSorley; A Millar; M H Osterhout; F Roschangar
Journal:  Org Lett       Date:  2001-05-31       Impact factor: 6.005

5.  A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction.

Authors:  Cyril Bressy; Dino Alberico; Mark Lautens
Journal:  J Am Chem Soc       Date:  2005-09-28       Impact factor: 15.419

6.  Pd-catalyzed decarboxylative arylation of thiazole, benzoxazole, and polyfluorobenzene with substituted benzoic acids.

Authors:  Kai Xie; Zhiyong Yang; Xingjian Zhou; Xiujian Li; Sizhuo Wang; Ze Tan; Xiangyu An; Can-Cheng Guo
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

7.  An aromatic Glaser-Hay reaction.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

8.  Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

Authors:  Gary A Molander; Belgin Canturk; Lauren E Kennedy
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

9.  Direct palladium-catalyzed C-3 arylation of free (NH)-indoles with aryl bromides under ligandless conditions.

Authors:  Fabio Bellina; Francesca Benelli; Renzo Rossi
Journal:  J Org Chem       Date:  2008-06-11       Impact factor: 4.354

10.  Rh(I)-catalyzed arylation of heterocycles via C-H bond activation: expanded scope through mechanistic insight.

Authors:  Jared C Lewis; Ashley M Berman; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2008-02-02       Impact factor: 15.419

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Journal:  RSC Adv       Date:  2020-05-19       Impact factor: 4.036

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3.  N-Heterocyclic carbene-palladium catalysts for the direct arylation of pyrrole derivatives with aryl chlorides.

Authors:  Ismail Ozdemir; Nevin Gürbüz; Nazan Kaloğlu; Oznur Doğan; Murat Kaloğlu; Christian Bruneau; Henri Doucet
Journal:  Beilstein J Org Chem       Date:  2013-02-12       Impact factor: 2.883

4.  Exploration of C-H and N-H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines.

Authors:  Michael Ghobrial; Marko D Mihovilovic; Michael Schnürch
Journal:  Beilstein J Org Chem       Date:  2014-09-15       Impact factor: 2.883

5.  Directed Evolution of RebH for Catalyst-Controlled Halogenation of Indole C-H Bonds.

Authors:  Mary C Andorfer; Hyun June Park; Jaylie Vergara-Coll; Jared C Lewis
Journal:  Chem Sci       Date:  2016-02-19       Impact factor: 9.825

  5 in total

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