Literature DB >> 16674054

(IPr)Pd(acac)Cl: an easily synthesized, efficient, and versatile precatalyst for C-N and C-C bond formation.

Nicolas Marion1, Elise C Ecarnot, Oscar Navarro, Dino Amoroso, Andrew Bell, Steven P Nolan.   

Abstract

A very straightforward synthesis of (IPr)Pd(acac)Cl from two commercially available starting materials, Pd(acac)2 and IPr.HCl [acac = acetylacetonate; IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], has been developed. The resulting complex, (IPr)Pd(acac)Cl (1), has proven to be a highly active PdII precatalyst in the Buchwald-Hartwig and the alpha-ketone arylation reactions. A wide range of substrates has been screened, including unactivated, sterically hindered, and heterocyclic aryl chlorides.

Entities:  

Year:  2006        PMID: 16674054     DOI: 10.1021/jo060190h

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  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.  Palladium-catalyzed regiocontrolled alpha-arylation of trimethylsilyl enol ethers with aryl halides.

Authors:  Tetsuo Iwama; Viresh H Rawal
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

3.  Palladium-Catalyzed β-Arylation of α-Keto Esters.

Authors:  Blane P Zavesky; Samuel L Bartlett; Jeffrey S Johnson
Journal:  Org Lett       Date:  2017-04-11       Impact factor: 6.005

4.  Selective monoarylation of acetate esters and aryl methyl ketones using aryl chlorides.

Authors:  Mark R Biscoe; Stephen L Buchwald
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005

5.  Highly reactive, general and long-lived catalysts for palladium-catalyzed amination of heteroaryl and aryl chlorides, bromides, and iodides: scope and structure-activity relationships.

Authors:  Qilong Shen; Tokutaro Ogata; John F Hartwig
Journal:  J Am Chem Soc       Date:  2008-04-30       Impact factor: 15.419

Review 6.  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

7.  [(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

8.  Nucleophilic addition to 2,3-pyridyne and synthesis of benzonaphthyridinones.

Authors:  Yuesi Fang; Richard C Larock
Journal:  Tetrahedron       Date:  2012-02-09       Impact factor: 2.457

9.  Synthesis of chiral mono(N-heterocyclic carbene) palladium and gold complexes with a 1,1'-biphenyl scaffold and their applications in catalysis.

Authors:  Lian-Jun Liu; Feijun Wang; Wenfeng Wang; Mei-Xin Zhao; Min Shi
Journal:  Beilstein J Org Chem       Date:  2011-05-04       Impact factor: 2.883

10.  Catalytic α-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.

Authors:  Enrico Marelli; Martin Corpet; Yury Minenkov; Rifahath M Neyyappadath; Alessandro Bismuto; Giulia Buccolini; Massimiliano Curcio; Luigi Cavallo; Steven P Nolan
Journal:  ACS Catal       Date:  2016-03-30       Impact factor: 13.084

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