Literature DB >> 18597473

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

Meihua Shen1, Tom G Driver.   

Abstract

The identity of the ortho-substituent of an aryl azide influences its reactivity toward transition metals. Substitution of a vinyl group with an imine disables rhodium(II)-mediated C-H amination and triggers a Lewis acid mechanism catalyzed by iron(II) bromide to facilitate benzimidazole formation.

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Year:  2008        PMID： 18597473     DOI： 10.1021/ol801227f

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


  11 in total

1.  Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; synthesis of dimebolin.

Authors:  Huijun Dong; Regina T Latka; Tom G Driver
Journal:  Org Lett       Date:  2011-04-25       Impact factor: 6.005

2.  Intramolecular Fe(II)-catalyzed N-O or N-N bond formation from aryl azides.

Authors:  Benjamin J Stokes; Carl V Vogel; Linda K Urnezis; Minjie Pan; Tom G Driver
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

3.  Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging.

Authors:  Rachel C Steinhardt; Jessica M O'Neill; Colin M Rathbun; David C McCutcheon; Miranda A Paley; Jennifer A Prescher
Journal:  Chemistry       Date:  2016-01-19       Impact factor: 5.236

4.  Oxidative condensations to form benzimidazole-substituted potassium organotrifluoroborates.

Authors:  Gary A Molander; Kehinde Ajayi
Journal:  Org Lett       Date:  2012-08-08       Impact factor: 6.005

5.  Rh2(II)-catalyzed nitro-group migration reactions: selective synthesis of 3-nitroindoles from β-nitro styryl azides.

Authors:  Benjamin J Stokes; Sheng Liu; Tom G Driver
Journal:  J Am Chem Soc       Date:  2011-03-14       Impact factor: 15.419

6.  Intramolecular Ir(I)-catalyzed benzylic C-H bond amination of ortho-substituted aryl azides.

Authors:  Ke Sun; Rachna Sachwani; Kathleen J Richert; Tom G Driver
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

7.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

8.  Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides.

Authors:  Quyen Nguyen; Tuyen Nguyen; Tom G Driver
Journal:  J Am Chem Soc       Date:  2013-01-03       Impact factor: 15.419

9.  A simple, efficient synthesis of 2-aryl benzimidazoles using silica supported periodic Acid catalyst and evaluation of anticancer activity.

Authors:  Vyankat A Sontakke; Sougata Ghosh; Pravin P Lawande; Balu A Chopade; Vaishali S Shinde
Journal:  ISRN Org Chem       Date:  2013-04-24

10.  Aqueous synthesis of 1-H-2-substituted benzimidazoles via transition-metal-free intramolecular amination of aryl iodides.

Authors:  Chunxia Chen; Chen Chen; Bin Li; Jingwei Tao; Jinsong Peng
Journal:  Molecules       Date:  2012-10-24       Impact factor: 4.411
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