Literature DB >> 22873832

Oxidative condensations to form benzimidazole-substituted potassium organotrifluoroborates.

Gary A Molander1, Kehinde Ajayi.   

Abstract

A library of benzimidazole-substituted potassium organotrifluoroborates was prepared via the condensation of various potassium formyl-substituted aryl- and heteroaryltrifluoroborates with aromatic 1,2-diamines under oxidative conditions. The efficient Suzuki-Miyaura cross-coupling of products thus formed to various aryl and heteroaryl bromides was achieved in good yields. The method allows the facile preparation of benzimidazole-containing triaromatic products in two steps from simple potassium formyl substituted aryl- or heteroaryltrifluoroborates.

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Year:  2012        PMID： 22873832      PMCID： PMC3428750          DOI： 10.1021/ol301956p

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


  32 in total

1.  Excited-state intramolecular proton transfer in 2-(2'-arylsulfonamidophenyl)benzimidazole derivatives: the effect of donor and acceptor substituents.

Authors:  Maged M Henary; Yonggang Wu; John Cody; S Sumalekshmy; Jing Li; Subrata Mandal; Christoph J Fahrni
Journal:  J Org Chem       Date:  2007-05-25       Impact factor: 4.354

2.  Structural competition between hydrogen bonds and halogen bonds.

Authors:  Christer B Aakeröy; Meg Fasulo; Nate Schultheiss; John Desper; Curtis Moore
Journal:  J Am Chem Soc       Date:  2007-10-23       Impact factor: 15.419

3.  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

4.  Dicationic near-linear biphenyl benzimidazole derivatives as DNA-targeted antiprotozoal agents.

Authors:  Mohamed A Ismail; Adalgisa Batista-Parra; Yi Miao; W David Wilson; Tanja Wenzler; Reto Brun; David W Boykin
Journal:  Bioorg Med Chem       Date:  2005-08-15       Impact factor: 3.641

5.  Synthesis of alpha-chloroaldoxime O-methanesulfonates and their use in the synthesis of functionalized benzimidazoles.

Authors:  Yuhei Yamamoto; Hiroo Mizuno; Takayuki Tsuritani; Toshiaki Mase
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

6.  Condensation reactions to form oxazoline-substituted potassium organotrifluoroborates.

Authors:  Gary A Molander; Wilma Febo-Ayala; Ludivine Jean-Gérard
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

7.  Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides.

Authors:  Meihua Shen; Tom G Driver
Journal:  Org Lett       Date:  2008-07-03       Impact factor: 6.005

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.  Design, selection, and characterization of thioflavin-based intercalation compounds with metal chelating properties for application in Alzheimer's disease.

Authors:  Cristina Rodríguez-Rodríguez; Natalia Sánchez de Groot; Albert Rimola; Angel Alvarez-Larena; Vega Lloveras; José Vidal-Gancedo; Salvador Ventura; Josep Vendrell; Mariona Sodupe; Pilar González-Duarte
Journal:  J Am Chem Soc       Date:  2009-02-04       Impact factor: 15.419

10.  Functionalization of organotrifluoroborates: reductive amination.

Authors:  Gary A Molander; David J Cooper
Journal:  J Org Chem       Date:  2008-04-16       Impact factor: 4.354
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  1 in total

1.  Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles: substrate scope and mechanistic investigation.

Authors:  M Alexander Düfert; Kelvin L Billingsley; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2013-08-16       Impact factor: 15.419
  1 in total

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