Literature DB >> 14627396

Selective amination of polyhalopyridines catalyzed by a palladium-xantphos complex.

Jianguo Ji1, Tao Li, William H Bunnelle.   

Abstract

[reaction: see text] Amination of 5-bromo-2-chloropyridine (1a) catalyzed by a palladium-Xantphos complex predominately gives 5-amino-2-chloropyridine product 3a in 96% isolated yield and excellent chemoselectivity (3a/4a = 97:3). Amination of 2,5-dibromopyridine (11) under the same conditions exclusively affords 2-amino-5-bromopyridine 4a.

Entities:  

Year:  2003        PMID： 14627396     DOI： 10.1021/ol0357696

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


  6 in total

1.  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

2.  Regioselective derivatizations of a tribrominated atropisomeric benzamide scaffold.

Authors:  Kimberly T Barrett; Scott J Miller
Journal:  Org Lett       Date:  2015-01-12       Impact factor: 6.005

3.  [(CyPF-(t)Bu)PdCl2]: an air-stable, one-component, highly efficient catalyst for amination of heteroaryl and aryl halides.

Authors:  Qilong Shen; John F Hartwig
Journal:  Org Lett       Date:  2008-08-21       Impact factor: 6.005

4.  Double N-arylation reaction of polyhalogenated 4,4'-bipyridines. Expedious synthesis of functionalized 2,7-diazacarbazoles.

Authors:  Mohamed Abboud; Emmanuel Aubert; Victor Mamane
Journal:  Beilstein J Org Chem       Date:  2012-02-14       Impact factor: 2.883

5.  A reactivity model for oxidative addition to palladium enables quantitative predictions for catalytic cross-coupling reactions.

Authors:  Jingru Lu; Sofia Donnecke; Irina Paci; David C Leitch
Journal:  Chem Sci       Date:  2022-02-28       Impact factor: 9.825

6.  N-Heterocyclic Carbene Ligand-Controlled Chemodivergent Suzuki-Miyaura Cross Coupling.

Authors:  Emily K Reeves; Jenna N Humke; Sharon R Neufeldt
Journal:  J Org Chem       Date:  2019-09-11       Impact factor: 4.198
  6 in total

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