Literature DB >> 18715012

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

Qilong Shen1, John F Hartwig.   

Abstract

An air- and moisture-stable palladium catalyst, [n class="Chemical">(CyPF-(t)Bu)PdCl2] (1), for coupling of heteroaryl chlorides, bromides, and iodides with a variety of primary amines is described. Most of these reactions occurred in high yield with 0.001-0.05 mol % catalyst loading. The reactions tolerated a wide range of functional groups.

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Year:  2008        PMID: 18715012      PMCID: PMC5677529          DOI: 10.1021/ol801615u

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


  24 in total

1.  The Synthesis of Aminopyridines: A Method Employing Palladium-Catalyzed Carbon-Nitrogen Bond Formation.

Authors:  Seble Wagaw; Stephen L. Buchwald
Journal:  J Org Chem       Date:  1996-10-18       Impact factor: 4.354

2.  Unparalleled rates for the activation of aryl chlorides and bromides: coupling with amines and boronic acids in minutes at room temperature.

Authors:  James P Stambuli; Ryoichi Kuwano; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2002-12-16       Impact factor: 15.336

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

Authors:  Michele C Harris; Xiaohua Huang; Stephen L Buchwald
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005

4.  An improved method for the palladium-catalyzed amination of aryl iodides.

Authors:  M H Ali; S L Buchwald
Journal:  J Org Chem       Date:  2001-04-20       Impact factor: 4.354

5.  Scope and limitations of the Pd/BINAP-catalyzed amination of aryl bromides.

Authors:  J P Wolfe; S L Buchwald
Journal:  J Org Chem       Date:  2000-02-25       Impact factor: 4.354

6.  Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems.

Authors:  G A Grasa; M S Viciu; J Huang; S P Nolan
Journal:  J Org Chem       Date:  2001-11-16       Impact factor: 4.354

7.  Pd-catalyzed N-arylation of heteroarylamines.

Authors:  Jingjun Yin; Matthew M Zhao; Mark A Huffman; James M McNamara
Journal:  Org Lett       Date:  2002-10-03       Impact factor: 6.005

8.  Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions.

Authors:  Nicolas Marion; Oscar Navarro; Jianguo Mei; Edwin D Stevens; Natalie M Scott; Steven P Nolan
Journal:  J Am Chem Soc       Date:  2006-03-29       Impact factor: 15.419

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

Authors:  Jianguo Ji; Tao Li; William H Bunnelle
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005

10.  Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C[bond]C, C[bond]N, and C[bond]O bond-forming cross-couplings.

Authors:  Noriyasu Kataoka; Quinetta Shelby; James P Stambuli; John F Hartwig
Journal:  J Org Chem       Date:  2002-08-09       Impact factor: 4.354

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  13 in total

1.  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

2.  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

3.  Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides.

Authors:  Ryan M Stolley; Michael T Maczka; Janis Louie
Journal:  European J Org Chem       Date:  2011-07

4.  Roles of Iron Complexes in Catalytic Radical Alkene Cross-Coupling: A Computational and Mechanistic Study.

Authors:  Dongyoung Kim; S M Wahidur Rahaman; Brandon Q Mercado; Rinaldo Poli; Patrick L Holland
Journal:  J Am Chem Soc       Date:  2019-04-26       Impact factor: 15.419

5.  Lithium perchlorate-nitromethane-promoted alkylation of anilines with arylmethanols.

Authors:  Jun Zhou; Hai-Feng Mao; Lu Wang; Jian-Ping Zou; Wei Zhang
Journal:  Mol Divers       Date:  2011-05-06       Impact factor: 2.943

6.  Iron-catalyzed formation of 2-aminopyridines from diynes and cyanamides.

Authors:  Timothy K Lane; Brendan R D'Souza; Janis Louie
Journal:  J Org Chem       Date:  2012-08-14       Impact factor: 4.354

Review 7.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

8.  Aryl Amination Using Soluble Weak Base Enabled by a Water-Assisted Mechanism.

Authors:  Sii Hong Lau; Peng Yu; Liye Chen; Christina B Madsen-Duggan; Michael J Williams; Brad P Carrow
Journal:  J Am Chem Soc       Date:  2020-11-12       Impact factor: 15.419

9.  A general, efficient, and functional-group-tolerant catalyst system for the palladium-catalyzed thioetherification of aryl bromides and iodides.

Authors:  Manuel A Fernández-Rodríguez; John F Hartwig
Journal:  J Org Chem       Date:  2009-02-20       Impact factor: 4.354

10.  Suzuki-Miyaura cross-coupling reaction on copper-trans-A(2)B corroles with excellent functional group tolerance.

Authors:  Michael König; Lorenz Michael Reith; Uwe Monkowius; Günther Knör; Klaus Bretterbauer; Wolfgang Schoefberger
Journal:  Tetrahedron       Date:  2011-06-10       Impact factor: 2.457

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