Literature DB >> 17288392

Phosphine-free palladium-catalyzed C-H bond arylation of free (N-H)-indoles and pyrroles.

Xiang Wang1, Denis V Gribkov, Dalibor Sames.   

Abstract

This paper describes a phosphine-free palladium-catalyzed method for direct C-arylation of free (N-H)-indoles and pyrroles with iodo- and bromoarene donors. Employing commercially available materials, this new and operationally simple procedure provides a rapid entry to a wide range of C-arylated (N-H)-indoles including derivatives of tryptamine. In the course of this study, a profound halide effect was uncovered, affecting both the efficiency and regioselectivity of indole arylation.

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Year:  2007        PMID： 17288392      PMCID： PMC2971669          DOI： 10.1021/jo061979v

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  22 in total

1.  Direct C-H bond arylation: selective palladium-catalyzed C2-arylation of N-substituted indoles.

Authors:  Benjamin S Lane; Dalibor Sames
Journal:  Org Lett       Date:  2004-08-19       Impact factor: 6.005

2.  Anilide ortho-arylation by using C-H activation methodology.

Authors:  Olafs Daugulis; Vladimir G Zaitsev
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-27       Impact factor: 15.336

3.  Efficient palladium-catalyzed N-arylation of indoles.

Authors:  D W Old; M C Harris; S L Buchwald
Journal:  Org Lett       Date:  2000-05-18       Impact factor: 6.005

4.  C-H bond functionalization in complex organic synthesis.

Authors:  Kamil Godula; Dalibor Sames
Journal:  Science       Date:  2006-04-07       Impact factor: 47.728

5.  Catalytic direct arylation with aryl chlorides, bromides, and iodides: intramolecular studies leading to new intermolecular reactions.

Authors:  Louis-Charles Campeau; Mathieu Parisien; Annie Jean; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2006-01-18       Impact factor: 15.419

6.  Concise synthesis of (+/-)-rhazinilam through direct coupling.

Authors:  Alfred L Bowie; Chambers C Hughes; Dirk Trauner
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

7.  Palladium-catalyzed cross-coupling of pyrrole anions with aryl chlorides, bromides, and iodides.

Authors:  Ryan D Rieth; Neal P Mankad; Elisa Calimano; Joseph P Sadighi
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

8.  Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems.

Authors:  G A Grasa; M S Viciu; J Huang; S P Nolan
Journal:  J Org Chem       Date:  2001-11-16       Impact factor: 4.354

9.  Palladium-catalyzed regioselective arylation of imidazo[1,2-a]pyrimidine.

Authors:  Wenjie Li; Dorian P Nelson; Mark S Jensen; R Scott Hoerrner; Gary J Javadi; Dongwei Cai; Robert D Larsen
Journal:  Org Lett       Date:  2003-12-11       Impact factor: 6.005

10.  Palladium-catalyzed arylation and heteroarylation of indolizines.

Authors:  Choul-Hong Park; Victoria Ryabova; Ilya V Seregin; Anna W Sromek; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2004-04-01       Impact factor: 6.005
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  16 in total

1.  C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

Authors:  Pengfei Guo; Jung Min Joo; Souvik Rakshit; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2011-09-22       Impact factor: 15.419

2.  Assessment of the intermediacy of arylpalladium carboxylate complexes in the direct arylation of benzene: evidence for C-H bond cleavage by "ligandless" species.

Authors:  Yichen Tan; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-02-11       Impact factor: 15.419

3.  C-H bonds as ubiquitous functionality: preparation of multiple regioisomers of arylated 1,2,4-triazoles via C-H arylation.

Authors:  Jung Min Joo; Pengfei Guo; Dalibor Sames
Journal:  J Org Chem       Date:  2012-12-31       Impact factor: 4.354

4.  Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems.

Authors:  Natalia Chernyak; David Tilly; Zhou Li; Vladimir Gevorgyan
Journal:  Chem Commun (Camb)       Date:  2009-11-17       Impact factor: 6.222

5.  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

6.  C-H bonds as ubiquitous functionality: a general approach to complex arylated imidazoles via regioselective sequential arylation of all three C-H bonds and regioselective N-alkylation enabled by SEM-group transposition.

Authors:  Jung Min Joo; B Barry Touré; Dalibor Sames
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

7.  C-H bonds as ubiquitous functionality: a general approach to complex arylated pyrazoles via sequential regioselective C-arylation and N-alkylation enabled by SEM-group transposition.

Authors:  Roman Goikhman; Teresa L Jacques; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419

8.  A Copper-Catalyzed Arylation of Tryptamines for the Direct Synthesis of Aryl Pyrroloindolines.

Authors:  Madeleine E Kieffer; Kangway V Chuang; Sarah E Reisman
Journal:  Chem Sci       Date:  2012-11       Impact factor: 9.825

9.  Cascade carbopalladation-annulation approach toward polycylic derivatives of indole and indolizine.

Authors:  Natalia Chernyak; David Tilly; Zhou Li; Vladimir Gevorgyan
Journal:  ARKIVOC       Date:  2010-12-10       Impact factor: 1.140

10.  N-Heterocyclic carbene-palladium catalysts for the direct arylation of pyrrole derivatives with aryl chlorides.

Authors:  Ismail Ozdemir; Nevin Gürbüz; Nazan Kaloğlu; Oznur Doğan; Murat Kaloğlu; Christian Bruneau; Henri Doucet
Journal:  Beilstein J Org Chem       Date:  2013-02-12       Impact factor: 2.883
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