Literature DB >> 17048852

Mild and general conditions for the cross-coupling of aryl halides with pentafluorobenzene and other perfluoroaromatics.

Marc Lafrance1, Daniel Shore, Keith Fagnou.   

Abstract

New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. These reactions occur in high yield and under mild conditions. Notably, the reactions can be performed at 80 degrees C in isopropyl acetate with a catalyst generated by the in situ mixing of Pd(OAc)(2) and S-Phos. The enhanced scope of these transformations should further reduce the need to use pentafluorophenylboronic acid in the construction of perfluoroarenes. [reaction: see text]

Entities:  

Year:  2006        PMID: 17048852     DOI: 10.1021/ol0619967

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


  16 in total

1.  Mechanistic studies on direct arylation of pyridine N-oxide: evidence for cooperative catalysis between two distinct palladium centers.

Authors:  Yichen Tan; Fabiola Barrios-Landeros; John F Hartwig
Journal:  J Am Chem Soc       Date:  2012-02-17       Impact factor: 15.419

Review 2.  Direct transition metal-catalyzed functionalization of heteroaromatic compounds.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2007-03-05       Impact factor: 54.564

3.  Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2008-01-09       Impact factor: 15.419

4.  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

5.  Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors:  Louis-Charles Campeau; Nilay Hazari
Journal:  Organometallics       Date:  2018-11-27       Impact factor: 3.876

6.  Synthesis of an electron-rich KITPHOS monophosphine, preparation of derived metal complexes and applications in catalysis.

Authors:  Simon Doherty; Catherine H Smyth; Julian G Knight; Stephen A K Hashmi
Journal:  Nat Protoc       Date:  2012-09-20       Impact factor: 13.491

7.  tBu3P-Coordinated 2-Phenylaniline-Based Palladacycle Complex As Precatalyst for Pd-Catalyzed Coupling Reactions of Aryl Halides with Polyfluoroarenes via C-H Activation Strategy.

Authors:  Hong-Hai Zhang; Jie Dong; Qiao-Sheng Hu
Journal:  European J Org Chem       Date:  2014-02-01

8.  A general method for copper-catalyzed arylation of arene C-H bonds.

Authors:  Hien-Quang Do; Rana M Kashif Khan; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2008-10-15       Impact factor: 15.419

9.  Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway.

Authors:  Natalia Chernyak; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-03-22       Impact factor: 15.419

10.  Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  Tetrahedron       Date:  2015-08-19       Impact factor: 2.457

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