Literature DB >> 24764603

Intramolecular arylation of benzimidazoles via Pd(II)/Cu(I) catalyzed cross-dehydrogenative coupling.

Kyle C Pereira1, Ashley L Porter1, Brenton Deboef1.   

Abstract

Electron poor benzimidazole substrates were arylated via an intramolecular cross-dehydrogenative coupling (CDC) reaction. These CDC reactions were catalyzed by a Pd(II)/Cu(I) catalyst system, capable of producing moderate yields on a large library of substrates. The substrate scope consisted of tethered arene-benzimidazoles that upon coupling, produced a fused polycyclic motif.

Entities:  

Keywords:  Biaryl; Cross-dehydrogenative coupling; Dual catalysis; Oxidative Coupling; Palladium

Year:  2014        PMID： 24764603      PMCID： PMC3993984          DOI： 10.1016/j.tetlet.2014.01.103

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  10 in total

1.  Design, synthesis, and SAR of heterocycle-containing antagonists of the human CCR5 receptor for the treatment of HIV-1 infection.

Authors:  D Kim; L Wang; C G Caldwell; P Chen; P E Finke; B Oates; M MacCoss; S G Mills; L Malkowitz; S L Gould; J A DeMartino; M S Springer; D Hazuda; M Miller; J Kessler; R Danzeisen; G Carver; A Carella; K Holmes; J Lineberger; W A Schleif; E A Emini
Journal:  Bioorg Med Chem Lett       Date:  2001-12-17       Impact factor: 2.823

2.  On the interpretation of deuterium kinetic isotope effects in C-H bond functionalizations by transition-metal complexes.

Authors:  Eric M Simmons; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-05       Impact factor: 15.336

3.  Synthesis of fused N-heterocycles via tandem C-H activation.

Authors:  Ge Meng; Hong-Ying Niu; Gui-Rong Qu; John S Fossey; Jian-Ping Li; Hai-Ming Guo
Journal:  Chem Commun (Camb)       Date:  2012-10-07       Impact factor: 6.222

4.  Palladium-catalyzed benzene arylation: incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design.

Authors:  Marc Lafrance; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

5.  Palladium-catalyzed oxidative C-H/C-H cross-coupling of indoles and pyrroles with heteroarenes.

Authors:  Zhen Wang; Kaizhi Li; Dongbing Zhao; Jingbo Lan; Jingsong You
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-13       Impact factor: 15.336

6.  Ligand-free copper(I)-catalysed intramolecular direct C-H functionalization of azoles.

Authors:  Nekane Barbero; Raul Sanmartin; Esther Domínguez
Journal:  Org Biomol Chem       Date:  2009-12-23       Impact factor: 3.876

7.  Discovery of the Poly(ADP-ribose) polymerase (PARP) inhibitor 2-[(R)-2-methylpyrrolidin-2-yl]-1H-benzimidazole-4-carboxamide (ABT-888) for the treatment of cancer.

Authors:  Thomas D Penning; Gui-Dong Zhu; Viraj B Gandhi; Jianchun Gong; Xuesong Liu; Yan Shi; Vered Klinghofer; Eric F Johnson; Cherrie K Donawho; David J Frost; Velitchka Bontcheva-Diaz; Jennifer J Bouska; Donald J Osterling; Amanda M Olson; Kennan C Marsh; Yan Luo; Vincent L Giranda
Journal:  J Med Chem       Date:  2009-01-22       Impact factor: 7.446

8.  Intramolecular Pd(II)-catalyzed oxidative biaryl synthesis under air: reaction development and scope.

Authors:  Benoît Liégault; Doris Lee; Malcolm P Huestis; David R Stuart; Keith Fagnou
Journal:  J Org Chem       Date:  2008-06-11       Impact factor: 4.354

9.  The catalytic cross-coupling of unactivated arenes.

Authors:  David R Stuart; Keith Fagnou
Journal:  Science       Date:  2007-05-25       Impact factor: 47.728

10.  Palladium(II)-catalyzed oxidative C-H/C-H cross-coupling of heteroarenes.

Authors:  Peihua Xi; Fan Yang; Song Qin; Dongbing Zhao; Jingbo Lan; Ge Gao; Changwei Hu; Jingsong You
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419
  10 in total
  2 in total

1.  C2-Selective Branched Alkylation of Benzimidazoles by Rhodium(I)-Catalyzed C-H Activation.

Authors:  Gaël Tran; Danielle Confair; Kevin D Hesp; Vincent Mascitti; Jonathan A Ellman
Journal:  J Org Chem       Date:  2017-08-22       Impact factor: 4.354

Review 2.  Advances in the Synthesis of Ring-Fused Benzimidazoles and Imidazobenzimidazoles.

Authors:  Martin Sweeney; Darren Conboy; Styliana I Mirallai; Fawaz Aldabbagh
Journal:  Molecules       Date:  2021-05-04       Impact factor: 4.411
  2 in total

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