Literature DB >> 19206211

Establishment of broadly applicable reaction conditions for the palladium-catalyzed direct arylation of heteroatom-containing aromatic compounds.

Benoît Liégault1, David Lapointe, Laurence Caron, Anna Vlassova, Keith Fagnou.   

Abstract

Conditions for the palladium-catalyzed direct arylation of a wide range of heterocycles with aryl bromides are reported. Those conditions employ a stoichiometric ratio of both coupling partners, as well as a substoichiometric quantity of pivalic acid, which results in significantly faster reactions. An evaluation of the influence of the nature of the aryl halide has also been carried out.

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Year:  2009        PMID： 19206211     DOI： 10.1021/jo8026565

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


  29 in total

1.  Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

2.  Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway.

Authors:  Natalia Chernyak; Serge I Gorelsky; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-07       Impact factor: 15.336

Review 3.  Chemistry and Biology of Resveratrol-Derived Natural Products.

Authors:  Mitchell H Keylor; Bryan S Matsuura; Corey R J Stephenson
Journal:  Chem Rev       Date:  2015-04-02       Impact factor: 60.622

4.  Palladium/Norbornene Cooperative Catalysis.

Authors:  Jianchun Wang; Guangbin Dong
Journal:  Chem Rev       Date:  2019-04-25       Impact factor: 60.622

5.  Direct C-H arylation of electron-deficient heterocycles with arylboronic acids.

Authors:  Ian B Seiple; Shun Su; Rodrigo A Rodriguez; Ryan Gianatassio; Yuta Fujiwara; Adam L Sobel; Phil S Baran
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

6.  Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis.

Authors:  Renhe Li; Yun Zhou; Xiaolong Xu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2019-11-22       Impact factor: 15.419

7.  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

8.  Palladium-catalyzed annulation of arynes by o-halobenzamides: synthesis of phenanthridinones.

Authors:  Chun Lu; Anton V Dubrovskiy; Richard C Larock
Journal:  J Org Chem       Date:  2012-09-26       Impact factor: 4.354

9.  Synthesis of Vitisins A and D Enabled by a Persistent Radical Equilibrium.

Authors:  Kevin J Romero; Mitchell H Keylor; Markus Griesser; Xu Zhu; Ethan J Strobel; Derek A Pratt; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2020-03-24       Impact factor: 15.419

10.  Evolution of C-H Bond Functionalization from Methane to Methodology.

Authors:  John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-12-15       Impact factor: 15.419
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