☆ 4.6 Article

Triflate-Selective Suzuki Cross-Coupling of Chloro- and Bromoaryl Triflates Under Ligand-Free Conditions

CHEMISTRY-AN ASIAN JOURNAL (2023)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Article Chemistry, Multidisciplinary

Solvent coordination to palladium can invert the selectivity of oxidative addition

Emily K. Elias et al.

Summary: The properties of the solvent affect the selectivity of the Pd/(PBu3)-Bu-t-catalyzed Suzuki-Miyaura reaction with chloroaryl triflates, with the selectivity change primarily due to solvent coordination to palladium. Polar coordinating and polar noncoordinating solvents lead to dramatically different selectivity. The role of solvent coordination is supported by stoichiometric oxidative addition experiments, density functional theory (DFT) calculations, and catalytic cross-coupling studies.

CHEMICAL SCIENCE (2022)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Salt-Enhanced Oxidative Addition of Iodobenzene to Pd: An Interplay Between Cation, Anion, and Pd-Pd Cooperative Effects

Haosheng Liang et al.

Summary: Halide salts facilitate the oxidative addition of organichalides to Pd(0) through a combination of anionic, cationic, and Pd-Pd cooperative effects. Chlorides promote phosphine release, leading to a mixture of mononuclear and dinuclear Pd(0) complexes. Anionic Pd(0) dinuclear complexes exhibit cooperativity between Pd(0) centers, favoring the oxidative addition of iodobenzene.

INORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Organic

Unconventional Site Selectivity in Palladium-Catalyzed Cross-Couplings of Dichloroheteroarenes under Ligand-Controlled and Ligand-Free Systems

Jacob P. Norman et al.

Summary: A highly selective method for cross-coupling reactions at the C4 position of 2,4-dichloropyridines was developed using a sterically hindered N-heterocyclic carbene ligand. The reaction showed high selectivity and broad scope, allowing for the formation of C4-C(sp2) and C4-C(sp3) bonds using organoboron, -zinc, and -magnesium reagents. Ligand-free conditions were also found to enhance the selectivity of the Suzuki coupling reaction by an order of magnitude, enabling the first C5-selective cross-couplings of 2,5-dichloropyridine and 2,5-dichloropyrimidine.

JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Physical

The Road Less Traveled: Unconventional Site Selectivity in Palladium-Catalyzed Cross-Couplings of Dihalogenated N-Heteroarenes

Jacob P. Norman et al.

Summary: The regiochemical outcomes of Pd-catalyzed cross-coupling reactions for most dihalogenated N-heteroarenes are well-established, but changes to the catalyst can lead to unconventional product due to different site selectivity. This Perspective surveys unusual cases controlled by ligands or catalyst speciation where divergent selectivity occurs. Some cases have established the mechanistic origin of inverted selectivity, while others remain unknown. The remaining challenges and opportunities in the field include understanding oxidative addition mechanisms, catalyst speciation, ring substituents influence, inverted selectivity for stubborn substrates, and minimizing over-reaction of di- and polyhalogenated substrates.

ACS CATALYSIS (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Chemodivergence between Electrophiles in Cross-Coupling Reactions

Emily K. Reeves et al.

Summary: Chemodivergent cross-couplings refer to reactions in which one potentially reactive functional group can be made to react based on choice of conditions. Factors influencing selectivity include catalyst ligation state, solvent polarity, and metal identity.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Bridging the Gap from Mononuclear PdII Precatalysts to Pd Nanoparticles: Identification of Intermediate Linear [Pd3(XPh3)4]2+ Clusters as Catalytic Species for Suzuki-Miyaura Couplings (X = P, As)

Kate M. Appleby et al.

Summary: Tripalladium clusters [Pd-3(PPh3)(4)](2+), stabilized by phosphine and arsine ligands, are detected and isolated as intermediates during the reduction of mononuclear Pd complexes to Pd nanoparticles. These clusters exhibit unexpected photoisomerization under UV irradiation and show catalytic activity in Suzuki-Miyaura cross-coupling reactions. Furthermore, they can alter site selectivity in reactions involving 2,4-dibromopyridine, showcasing their potential as catalysts for various transformations.

ORGANOMETALLICS (2021)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Comparative study of aryl halides in Pd-mediated reactions: key factors beyond the oxidative addition step

Alexey S. Galushko et al.

Summary: Catalytic transformations involving aryl chlorides are challenging, even though the slow oxidative addition to palladium catalyst is usually considered the main reason for low reactivity. However, other factors were found to also significantly influence the reactivity of aryl halides, suggesting a need for a substantial revision of catalyst design principles.

INORGANIC CHEMISTRY FRONTIERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Solvent Effects on the Selectivity of Palladium-Catalyzed Suzuki-Miyaura Couplings

Emily K. Reeves et al.

ISRAEL JOURNAL OF CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Organic

N-Heterocyclic Carbene Ligand-Controlled Chemodivergent Suzuki-Miyaura Cross Coupling

Emily K. Reeves et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Modular Functionalization of Arenes in a Triply Selective Sequence: Rapid C(sp(2)) and C(sp(3)) Coupling of C-Br, C-OTf, and C-Cl Bonds Enabled by a Single Palladium(I) Dimer

Sinead T. Keaveney et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Article Chemistry, Physical

First-Principles Molecular Dynamics Analysis of Ligand-Free Suzuki-Miyaura Cross-Coupling in Water Solvent: Oxidative Addition Step

Teruo Hirakawa et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ligand- and Solvent-Tuned Chemoselective Carbonylation of Bromoaryl Triflates

Chaoren Shen et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

添加到收藏夹

Article Multidisciplinary Sciences

Multimetallic catalysed cross-coupling of aryl bromides with aryl triflates

Laura K. G. Ackerman et al.

NATURE (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Solvent Effect on Palladium-Catalyzed Cross-Coupling Reactions and Implications on the Active Catalytic Species

Fabien Proutiere et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ligand-Controlled Regioselectivity in Palladium-Catalyzed Cross Coupling Reactions

Franziska Schoenebeck et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Oxidative addition of aryl chlorides to monoligated palladium(0): A DFT-SCRF study

Marten Ahlquist et al.

ORGANOMETALLICS (2007)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Effects of bases and halides on the amination of chloroarenes catalyzed by Pd(PtBu3)2

Shashank Shekhar et al.

ORGANOMETALLICS (2007)

添加到收藏夹

Article Chemistry, Multidisciplinary

Heterogeneous Pd/C-catalyzed ligand-free, room-temperature Suzuki-Miyaura coupling reactions in aqueous media

Tomohiro Maegawa et al.

CHEMISTRY-A EUROPEAN JOURNAL (2007)

添加到收藏夹

Article Chemistry, Multidisciplinary

Aryl bromide/triflate selectivities reveal mechanistic divergence in palladium-catalysed couplings; the Suzuki-Miyaura anomaly

Gustavo Espino et al.

CHEMICAL COMMUNICATIONS (2007)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Theoretical evidence for low-ligated palladium(0): [Pd-L] as the active species in oxidative addition reactions

M Ahlquist et al.

ORGANOMETALLICS (2006)

添加到收藏夹

Article Chemistry, Multidisciplinary

A combined kinetic-quantum mechanical model for assessment of catalytic cycles: Application to cross-coupling and Heck reactions

S Kozuch et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Palladium monophosphine intermediates in catalytic cross-coupling reactions: A DFT study

LJ Goossen et al.

ORGANOMETALLICS (2006)

添加到收藏夹

Article Chemistry, Multidisciplinary

The palladium-catalyzed cross-coupling reaction of carboxylic anhydrides with arylboronic acids: A DFT study

LJ Goossen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Mechanistic pathways for oxidative addition of aryl halides to palladium(0) complexes: A DFT study

LJ Goossen et al.

ORGANOMETALLICS (2005)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Oxidative addition of aryl Sulfonates to Palladium(0) complexes of mono- and bidentate phosphines. Mild addition of aryl tosylates and the effects of anions on rate and mechanism

AH Roy et al.

ORGANOMETALLICS (2004)

添加到收藏夹

Article Chemistry, Multidisciplinary

Active anionic zero-valent palladium catalysts: Characterization by density functional calculations

S Kozuch et al.

CHEMISTRY-A EUROPEAN JOURNAL (2004)

添加到收藏夹

Article Chemistry, Multidisciplinary

The mechanism of the oxidative addition of aryl halides to Pd-catalysts: a DFT investigation

LJ Goossen et al.

CHEMICAL COMMUNICATIONS (2004)

添加到收藏夹

Article Chemistry, Organic

Efficient ligandless palladium-catalyzed Suzuki reactions of potassium aryltrifluoroborates

GA Molander et al.

ORGANIC LETTERS (2002)

添加到收藏夹

Article Chemistry, Multidisciplinary

Mechanism of aryl chloride amination: Base-induced oxidative addition

LM Alcazar-Roman et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

添加到收藏夹

Article Chemistry, Multidisciplinary

Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions

AF Littke et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)

添加到收藏夹

Review Chemistry, Multidisciplinary

Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions

C Amatore et al.

ACCOUNTS OF CHEMICAL RESEARCH (2000)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.