Literature DB >> 19877661

Intermolecular decarboxylative direct C-3 arylation of indoles with benzoic acids.

Josep Cornella1, Pengfei Lu, Igor Larrosa.   

Abstract

A palladium catalyzed C-H activation of indoles and a silver catalyzed decarboxylative C-C activation of ortho substituted benzoic acids are synergistically combined to synthesize indoles arylated exclusively in the C-3 position. This novel decarboxylative C-H arylation methodology is compatible with electron-donating and -withdrawing substituents in both coupling partners.

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Year:  2009        PMID: 19877661     DOI: 10.1021/ol902304n

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


  11 in total

1.  A general method for copper-catalyzed arene cross-dimerization.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-08-08       Impact factor: 15.419

2.  Nickel-Catalyzed Decarboxylative Arylation of Azoles with Perfluoro- and Nitrobenzoates.

Authors:  Jennifer M Crawford; Kyle E Shelton; Emily K Reeves; Bryce K Sadarananda; Dipannita Kalyani
Journal:  Org Chem Front       Date:  2015-05-12       Impact factor: 5.281

3.  Palladium-catalyzed indole, pyrrole, and furan arylation by aryl chlorides.

Authors:  Enrico T Nadres; Anna Lazareva; Olafs Daugulis
Journal:  J Org Chem       Date:  2010-12-30       Impact factor: 4.354

4.  Transition-Metal-Free C3 Arylation of Indoles with Aryl Halides.

Authors:  Ji Chen; Jimmy Wu
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-03       Impact factor: 15.336

5.  Nickel-catalyzed decarboxylative cross-coupling of perfluorobenzoates with aryl halides and sulfonates.

Authors:  Logan W Sardzinski; William C Wertjes; Abigail M Schnaith; Dipannita Kalyani
Journal:  Org Lett       Date:  2015-02-20       Impact factor: 6.005

Review 6.  Recent Progress in Decarboxylative Oxidative Cross-Coupling for Biaryl Synthesis.

Authors:  Gregory J P Perry; Igor Larrosa
Journal:  European J Org Chem       Date:  2017-04-26

7.  Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings.

Authors:  Gregory J P Perry; Jacob M Quibell; Adyasha Panigrahi; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2017-08-08       Impact factor: 15.419

8.  Room-temperature Pd/Ag direct arylation enabled by a radical pathway.

Authors:  Amy L Mayhugh; Christine K Luscombe
Journal:  Beilstein J Org Chem       Date:  2020-03-13       Impact factor: 2.883

9.  Exploration of C-H and N-H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines.

Authors:  Michael Ghobrial; Marko D Mihovilovic; Michael Schnürch
Journal:  Beilstein J Org Chem       Date:  2014-09-15       Impact factor: 2.883

10.  Regioselective Pd-catalyzed direct C1- and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-ij]quinoline derivatives.

Authors:  Hai-Yun Huang; Haoran Li; Thierry Roisnel; Jean-François Soulé; Henri Doucet
Journal:  Beilstein J Org Chem       Date:  2019-08-29       Impact factor: 2.883

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