Literature DB >> 16231894

Combined C-H functionalization/C-N bond formation route to carbazoles.

W C Peter Tsang1, Nan Zheng, Stephen L Buchwald.   

Abstract

A new method in which a series of substituted carbazoles is efficiently produced by the combination of an n class="Chemical">amide and an arene is described. The key feature of this method is the palladium-catalyzed tandem directed C-H functionalization and amide arylation. The method tolerates substitution on either ring of the biaryl amide substrates, and the products can be assembled in a simple two-step protocol from readily available reagents. The Pd(0) species generated are reoxidized to Pd(II) in the presence of Cu(OAc)2 and an atmosphere of oxygen.

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Year:  2005        PMID: 16231894     DOI: 10.1021/ja055353i

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  39 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.  Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Authors:  Tian-Sheng Mei; Lei Kou; Sandy Ma; Keary M Engle; Jin-Quan Yu
Journal:  Synthesis (Stuttg)       Date:  2012-05-25       Impact factor: 3.157

3.  Synthesis of Unsymmetrical 2,6-Diarylanilines by Palladium-Catalyzed C-H Bond Functionalization Methodology.

Authors:  Se Hun Kwak; Nurbey Gulia; Olafs Daugulis
Journal:  J Org Chem       Date:  2018-05-08       Impact factor: 4.354

4.  Palladium(0)-catalyzed intermolecular amination of unactivated C(sp³)-H bonds.

Authors:  Jun Pan; Mingjuan Su; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-02       Impact factor: 15.336

5.  Metal-free intermolecular oxidative C-N bond formation via tandem C-H and N-H bond functionalization.

Authors:  Abhishek A Kantak; Shathaverdhan Potavathri; Rose A Barham; Kaitlyn M Romano; Brenton DeBoef
Journal:  J Am Chem Soc       Date:  2011-11-16       Impact factor: 15.419

6.  Twofold C-H functionalization: palladium-catalyzed ortho arylation of anilides.

Authors:  Gordon Brasche; Jorge García-Fortanet; Stephen L Buchwald
Journal:  Org Lett       Date:  2008-05-09       Impact factor: 6.005

7.  Regioselective C-H bond amination by aminoiodanes.

Authors:  Abhishek A Kantak; Louis Marchetti; Brenton DeBoef
Journal:  Chem Commun (Camb)       Date:  2015-02-28       Impact factor: 6.222

8.  Rh(2)(II)-catalyzed synthesis of carbazoles from biaryl azides.

Authors:  Benjamin J Stokes; Brankica Jovanović; Huijun Dong; Kathleen J Richert; Ryan D Riell; Tom G Driver
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

9.  Directed amination of non-acidic arene C-H bonds by a copper-silver catalytic system.

Authors:  Ly Dieu Tran; James Roane; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-24       Impact factor: 15.336

10.  Insights into directing group ability in palladium-catalyzed C-H bond functionalization.

Authors:  Lopa V Desai; Kara J Stowers; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2008-09-10       Impact factor: 15.419

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