Highly Active Pd-PEPPSI Complexes for Suzuki-Miyaura Cross-coupling of Aryl Chlorides: an Investigation on the Effect of Electronic Properties

Amidation of 1'-(diphenylphosphanyl)ferrocene-1-carboxylic acid (Hdpf) with ethane-1,2-diamine afforded N,N'-ethylenebis[1'-(diphenylphosphanyl)ferrocene-1-carboxamide] (1), which was isolated in free and solvated form, 1·2AcOH. Both 1 and Hdpf were further converted to their respective phosphane sulfides, 2·2AcOH and 3 that were structurally characterized. Testing of the amidophosphane ligands in Suzuki-Miyaura cross-coupling reaction between phenylboronic acid and various aryl halides revealed that catalyst formed in situ from 1 and palladium(II) acetate is highly active in coupling reactions of aryl bromides whilst the corresponding aryl chlorides showed no or only poor conversions. The catalyst based on 2·2AcOH gave markedly lower yields of the coupling products.

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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

Journal of the American Chemical Society ◽

10.1021/ja8055358 ◽

2008 ◽

Vol 130 (41) ◽

pp. 13552-13554 ◽

Cited By ~ 372

Author(s):

Brett P. Fors ◽

Donald A. Watson ◽

Mark R. Biscoe ◽

Stephen L. Buchwald

Keyword(s):

Active Catalyst ◽

Cross Coupling ◽

Primary Amines ◽

Coupling Reactions ◽

Aryl Chlorides ◽

Cross Coupling Reactions ◽

Highly Active

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Highly Active Pd-PEPPSI Complexes for Suzuki-Miyaura Cross-coupling of Aryl Chlorides: an Investigation on the Effect of Electronic Properties

Highly Active, Air-Stable Versatile Palladium Catalysts for the C−C, C−N, and C−S Bond Formations via Cross-Coupling Reactions of Aryl Chlorides

ChemInform Abstract: 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.

ChemInform Abstract: Highly Active, Well-Defined (Cyclopentadiene)(N-heterocyclic carbene)palladium Chloride Complexes for Room-Temperature SuzukiâMiyaura and BuchwaldâHartwig Cross-Coupling Reactions of Aryl Chlorides and Deboronation Homocoupling of Arylboronic Acids.

Highly active, air-stable palladium catalysts for Kumada–Tamao–Corriu cross-coupling reaction of inactivated aryl chlorides with aryl Grignard reagents

Highly Active [Pd(μ-Cl)(Cl)(NHC)]2(NHC = N-Heterocyclic Carbene) in the Cross-Coupling of Grignard Reagents with Aryl Chlorides

Aryl Grignard cross-coupling of aryl chlorides catalysed by new, highly active phosphine/imidazolium nickel(II) complexes

Highly Active, Well-Defined (Cyclopentadiene)(N-heterocyclic carbene)palladium Chloride Complexes for Room-Temperature Suzuki-Miyaura and Buchwald-Hartwig Cross-Coupling Reactions of Aryl Chlorides and Deboronation Homocoupling of Arylboronic Acids

A Highly Active Catalyst for Palladium-Catalyzed Cross-Coupling Reactions: Room-Temperature Suzuki Couplings and Amination of Unactivated Aryl Chlorides

Synthesis, Characterization and Catalytic Utilization of a Ferrocene Diamidodiphosphane

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

ChemInform Abstract: Highly Active, Well-Defined (Cyclopentadiene)(N-heterocyclic carbene)palladium Chloride Complexes for Room-Temperature SuzukiâMiyaura and BuchwaldâHartwig Cross-Coupling Reactions of Aryl Chlorides and Deboronation Homocoupling of Arylboronic Acids.