Literature DB >> 12182580

Improved functional group compatibility in the palladium-catalyzed synthesis of aryl amines.

Michele C Harris1, Xiaohua Huang, Stephen L Buchwald.   

Abstract

[reaction: see text] The use of Pd2dba3 with bulky, electron-rich ligands 1 or 2 and LiN(TMS)2 as the base for the coupling of amines with aryl halides containing hydroxyl, amide, or enolizable keto groups is described. This protocol expands the utility of palladium-catalyzed C-N bond formation by allowing for the use of aryl halides containing these functional groups, obviating the need for protecting group manipulations.

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Year:  2002        PMID： 12182580     DOI： 10.1021/ol0262688

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


  18 in total

1.  Design, synthesis, and molecular modeling of novel pyrido[2,3-d]pyrimidine analogues as antifolates; application of Buchwald-Hartwig aminations of heterocycles.

Authors:  Aleem Gangjee; Ojas A Namjoshi; Sudhir Raghavan; Sherry F Queener; Roy L Kisliuk; Vivian Cody
Journal:  J Med Chem       Date:  2013-05-21       Impact factor: 7.446

2.  Palladium-Catalyzed Coupling of Functionalized Primary and Secondary Amines with Aryl and Heteroaryl Halides: Two Ligands Suffice in Most Cases.

Authors:  Debabrata Maiti; Brett P Fors; Jaclyn L Henderson; Yoshinori Nakamura; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011-01-01       Impact factor: 9.825

3.  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

4.  Structure-Activity Study of Bioisosteric Trifluoromethyl and Pentafluorosulfanyl Indole Inhibitors of the AAA ATPase p97.

Authors:  Celeste Alverez; Michelle R Arkin; Stacie L Bulfer; Raffaele Colombo; Marina Kovaliov; Matthew G LaPorte; Chaemin Lim; Mary Liang; William J Moore; R Jeffrey Neitz; Yongzhao Yan; Zhizhou Yue; Donna M Huryn; Peter Wipf
Journal:  ACS Med Chem Lett       Date:  2015-10-23       Impact factor: 4.345

5.  Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling.

Authors:  Joseph M Dennis; Nicholas A White; Richard Y Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-03-22       Impact factor: 15.419

6.  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

7.  Design, synthesis, and biological activity of substituted 2-amino-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acid derivatives as inhibitors of the inflammatory kinases TBK1 and IKKε for the treatment of obesity.

Authors:  Tyler S Beyett; Xinmin Gan; Shannon M Reilly; Andrew V Gomez; Louise Chang; John J G Tesmer; Alan R Saltiel; Hollis D Showalter
Journal:  Bioorg Med Chem       Date:  2018-09-20       Impact factor: 3.641

8.  In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination.

Authors:  David B Berkowitz; Weijun Shen; Gourhari Maiti
Journal:  Tetrahedron Asymmetry       Date:  2004-09-13

9.  Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

Authors:  John F Hartwig
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

10.  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
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