Literature DB >> 21818164

Simple, Efficient Protocols for the Pd-Catalyzed Cross-Coupling Reaction of Aryl Chlorides and Dimethylamine.

Brian K Lee1, Mark R Biscoe, Stephen L Buchwald.   

Abstract

Simple and efficient procedures for the Pd-catalyzed cross-coupling reaction of n class="Chemical">aryl chlorides and dimethylamine are described. At room temperature with a strong base, t-BuXPhos is employed as the supporting ligand; at 110 °C with a weak base, XPhos is employed as the supporting ligand. In each of these cases, commercially available solutions constitute the source of the dimethylamine, and recently disclosed precatalysts constitute the source of the ligand and Pd. This work further expands the utility of these precatalysts in reactions that benefit from an easily activated source of L(1)Pd(0).

Entities:  

Year:  2009        PMID: 21818164      PMCID: PMC3148836          DOI: 10.1016/j.tetlet.2009.03.137

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  6 in total

1.  A practical Buchwald-Hartwig amination of 2-bromopyridines with volatile amines.

Authors:  Jie Jack Li; Zhi Wang; Lorna H Mitchell
Journal:  J Org Chem       Date:  2007-04-07       Impact factor: 4.354

2.  An improved protocol for the Pd-catalyzed alpha-arylation of aldehydes with aryl halides.

Authors:  Rubén Martín; Stephen L Buchwald
Journal:  Org Lett       Date:  2008-09-23       Impact factor: 6.005

Review 3.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  A new class of easily activated palladium precatalysts for facile C-N cross-coupling reactions and the low temperature oxidative addition of aryl chlorides.

Authors:  Mark R Biscoe; Brett P Fors; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2008-05-01       Impact factor: 15.419

5.  A highly active catalyst for Pd-catalyzed amination reactions: cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides.

Authors:  Brett P Fors; Donald A Watson; Mark R Biscoe; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2008-09-18       Impact factor: 15.419

6.  Modular and practical synthesis of 6-substituted pyridin-3-yl C-nucleosides.

Authors:  Nicolas Joubert; Radek Pohl; Blanka Klepetérová; Michal Hocek
Journal:  J Org Chem       Date:  2007-08-01       Impact factor: 4.354

  6 in total
  3 in total

1.  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

2.  Palladium-catalyzed C,N-cross coupling reactions of 3-halo-2-aminopyridines.

Authors:  Felix Perez; Ana Minatti
Journal:  Org Lett       Date:  2011-03-25       Impact factor: 6.005

3.  A thermal dehydrogenative Diels-Alder reaction of styrenes for the concise synthesis of functionalized naphthalenes.

Authors:  Laura S Kocsis; Erica Benedetti; Kay M Brummond
Journal:  Org Lett       Date:  2012-08-22       Impact factor: 6.005

  3 in total

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