Literature DB >> 10804564

Palladium-catalyzed intermolecular coupling of aryl halides and amides.

J Yin1, S L Buchwald.   

Abstract

[formula: see text] The first general intermolecular C-N bond-forming reactions between aryl halides and amides were realized using a palladium catalyst with Xantphos as the ligand. Aryl triflates, carbamates, and sulfonamides are also viable substrates for the amidations, which proceed at 45-110 degrees C with 1-4 mol% of Pd catalyst in 66-99% yields and exhibit good functional group compatibility.

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Year:  2000        PMID: 10804564     DOI: 10.1021/ol005654r

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


  25 in total

1.  Palladium-catalyzed arylation of cyanamides.

Authors:  Ryan M Stolley; Wenxing Guo; Janis Louie
Journal:  Org Lett       Date:  2011-12-05       Impact factor: 6.005

2.  Ammonia synthons for the multicomponent assembly of complex gamma-lactams.

Authors:  Darlene Q Tan; Kevin S Martin; James C Fettinger; Jared T Shaw
Journal:  Proc Natl Acad Sci U S A       Date:  2011-02-02       Impact factor: 11.205

3.  Lewis acid acceleration of C-N bond-forming reductive elimination from heteroarylpalladium complexes and catalytic amidation of heteroaryl bromides.

Authors:  Qilong Shen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2007-06-02       Impact factor: 15.419

4.  Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers.

Authors:  Dake Chen; Ilyas A Berhane; Sherry R Chemler
Journal:  Org Lett       Date:  2020-06-04       Impact factor: 6.005

5.  A bulky biaryl phosphine ligand allows for palladium-catalyzed amidation of five-membered heterocycles as electrophiles.

Authors:  Mingjuan Su; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-30       Impact factor: 15.336

6.  Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis.

Authors:  Taehoon Kim; Stefan J McCarver; Chulbom Lee; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-27       Impact factor: 15.336

7.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

8.  Mechanistic studies on the copper-catalyzed N-arylation of amides.

Authors:  Eric R Strieter; Brijesh Bhayana; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-01-14       Impact factor: 15.419

9.  Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study.

Authors:  Jacqueline D Hicks; Alan M Hyde; Alberto Martinez Cuezva; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

10.  Discovery of VU0431316: a negative allosteric modulator of mGlu5 with activity in a mouse model of anxiety.

Authors:  Brittney S Bates; Alice L Rodriguez; Andrew S Felts; Ryan D Morrison; Daryl F Venable; Anna L Blobaum; Frank W Byers; Kera P Lawson; J Scott Daniels; Colleen M Niswender; Carrie K Jones; P Jeffrey Conn; Craig W Lindsley; Kyle A Emmitte
Journal:  Bioorg Med Chem Lett       Date:  2014-06-11       Impact factor: 2.823

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