Literature DB >> 15113190

Synthesis, structure, and reductive elimination chemistry of three-coordinate arylpalladium amido complexes.

Makoto Yamashita1, John F Hartwig.   

Abstract

Four three-coordinate arylpalladium amido complexes with a single hindered phosphine were isolated and structurally characterized. Each possessed a T-shaped geometry. Several of these complexes possessed true three-coordinate structures that lacked any additional coordination by ligand C-H bonds. All of the three-coordinate complexes underwent reductive elimination to form the corresponding triarylamine. A comparison of the rate of reaction of the three-coordinate compounds demonstrated that the rate of elimination from the pentaphenylferrocenyl di-tert-butylphosphine complex were the fastest. A comparison of the rates of reactions between three-coordinate and four-coordinate complexes showed that the rates were much faster from the three-coordinate complexes.

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Year:  2004        PMID: 15113190     DOI: 10.1021/ja0315107

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  16 in total

1.  Palladium-catalyzed alkene carboamination reactions for the synthesis of substituted piperazines.

Authors:  Josephine S Nakhla; Danielle M Schultz; John P Wolfe
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

2.  A rigid cyclic (alkyl)(amino)carbene ligand leads to isolation of low-coordinate transition-metal complexes.

Authors:  Vincent Lavallo; Yves Canac; Alan DeHope; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-11       Impact factor: 15.336

3.  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

4.  Reductive elimination of ether from T-shaped, monomeric arylpalladium alkoxides.

Authors:  James P Stambuli; Zhiqiang Weng; Christopher D Incarvito; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Assessment of the intermediacy of arylpalladium carboxylate complexes in the direct arylation of benzene: evidence for C-H bond cleavage by "ligandless" species.

Authors:  Yichen Tan; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-02-11       Impact factor: 15.419

6.  Probing the Electronic Demands of Transmetalation in the Palladium-Catalyzed Cross-Coupling of Arylsilanolates.

Authors:  Scott E Denmark; Russell C Smith; Wen-Tau T Chang
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

Review 7.  Stable cyclic carbenes and related species beyond diaminocarbenes.

Authors:  Mohand Melaimi; Michèle Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

8.  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

9.  New strategy for the synthesis of substituted morpholines.

Authors:  Matthew L Leathen; Brandon R Rosen; John P Wolfe
Journal:  J Org Chem       Date:  2009-07-17       Impact factor: 4.354

10.  Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.

Authors:  Bryan T Ingoglia; Corin C Wagen; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2019-05-11       Impact factor: 2.457

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