Literature DB >> 18998652

Oxidative Pd(II)-catalyzed C-H bond amination to carbazole at ambient temperature.

James A Jordan-Hore1, Carin C C Johansson, Elizabeth M Beck, Matthew J Gaunt.   

Abstract

We report a new Pd(II)-catalyzed C-H bond amination reaction to form carbazoles, an important motif that is prevalent in a range of systems. The catalytic amination process operates under extremely mild conditions and produces carbazole products in good to excellent yields. Carbazoles possessing complex molecular architecture can also be formed using this reaction, highlighting its potential in natural product synthesis applications. Preliminary mechanistic investigations reveal the reaction proceeds through a Pd(II)/Pd(IV) manifold and that reductive elimination from a high oxidation state Pd(IV) complex facilitates the mild conditions of this transformation.

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Year:  2008        PMID: 18998652     DOI: 10.1021/ja806543s

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


  45 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.  Controlling factors for C-H functionalization versus cyclopropanation of dihydronaphthalenes.

Authors:  Etienne Nadeau; Dominic L Ventura; Jonathan A Brekan; Huw M L Davies
Journal:  J Org Chem       Date:  2010-03-19       Impact factor: 4.354

4.  On the mechanism of palladium-catalyzed aromatic C-H oxidation.

Authors:  David C Powers; Daphne Y Xiao; Matthias A L Geibel; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

5.  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

6.  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

Review 7.  Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry.

Authors:  Felipe Cesar Sousa E Silva; Anthony F Tierno; Sarah E Wengryniuk
Journal:  Molecules       Date:  2017-05-12       Impact factor: 4.411

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.  Copper-mediated amidation of heterocyclic and aromatic C-H bonds.

Authors:  Qiu Wang; Stuart L Schreiber
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

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