4.8 Article

Important Role of NH-Carbazole in Aryl Amination Reactions Catalyzed by 2-Aminobiphenyl Palladacycles

Related references

Note: Only part of the references are listed.
Review Chemistry, Multidisciplinary

Emerging Trends in Cross-Coupling: Twelve-Electron-Based L1Pd(0) Catalysts, Their Mechanism of Action, and Selected Applications

Sharbil J. Firsan et al.

Summary: Monoligated palladium(0) species, L1Pd(0), are the most active catalytic species in cross-coupling reactions. Highly active but unstable L1Pd(0) catalysts can be generated from stable precatalysts. The size of the ligand plays a crucial role in the formation of L1Pd(0), and it can be precisely formed from the precatalyst using various technologies.

CHEMICAL REVIEWS (2022)

Review Chemistry, Multidisciplinary

Catalysis with Palladium(I) Dimers

Christoph Fricke et al.

Summary: Dinuclear Pd-I complexes have diverse applications as catalysts, triggering privileged reactivities and couplings that would not engage in Pd-0/Pd-II catalysis. Research focuses on mechanistic intricacies, speciation, and impacts on reactivity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Computational Analysis on the Pd-Catalyzed C-N Coupling of Ammonia with Aryl Bromides Using a Chelate Phosphine Ligand

Pablo Gomez-Orellana et al.

Summary: The Buchwald-Hartwig amination of arylhalides with the Pd-Josiphos complex using ammonia as a reactant is a useful process for primary amine synthesis. Density-functional theory calculations were used to examine the reaction mechanism, revealing the importance of the chelate phosphine ligand and base in the process. The study allowed for the proposal of a complete reaction mechanism for the Pd-catalyzed C-N coupling reaction.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Inorganic & Nuclear

N-substituted aminobiphenyl palladacycles stabilized by dialkylterphenyl phosphanes: Preparation and applications in C-N cross-coupling reactions

Andrea Monti et al.

Summary: The study presented the synthesis and characterization of neutral and cationic N-methyl- and N-phenyl-2-aminobiphenyl methanesulfonate palladacycles stabilized with dialkylterphenyl phosphines. By selecting different phosphine ligands, different coordination modes and structures of complexes were obtained. The most efficient precatalyst, [Pd(N-methyl-2-aminobiphenyl)L4](OMs), was identified for facilitating the coupling of aryl chlorides with secondary and primary amines and indoles.

INORGANICA CHIMICA ACTA (2021)

Article Chemistry, Multidisciplinary

Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions

Nardana Sivendran et al.

Summary: Halogen-bridged methylnaphthyl (MeNAP) palladium dimers, presented as versatile Pd precursors, demonstrate excellent catalytic performance by in situ conversion into well-defined monoligated complexes. They show benchmark activities in challenging reactions, enable record-setting yields, and can achieve previously elusive cross-couplings.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Faster palladium-catalyzed arylation of simple arenes in the presence of a methylketone: beneficial effect of an a priori interfering solvent in C-H activation

Vanesa Salamanca et al.

Summary: Functionalization of simple arenes is challenging, as it requires cleaving the sluggish C-H bond and overcoming the weak coordinating ability of the arene pi-system. Using a well-defined palladium complex with a specific ligand and a moderately coordinating solvent can decrease the amount of arene used, while a co-solvent like t-butyl methyl ketone can accelerate the reaction process by altering the concentration and stability of relevant metal species.

ORGANIC CHEMISTRY FRONTIERS (2021)

Review Chemistry, Multidisciplinary

Development of Palladium Precatalysts that Efficiently Generate LPd(0) Active Species

Kevin H. Shaughnessy

ISRAEL JOURNAL OF CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Dialkylterphenyl Phosphine-Based Palladium Precatalysts for Efficient Aryl Amination of N-Nucleophiles

Raquel J. Rama et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Multidisciplinary

Development of an Aryl Amination Catalyst with Broad Scope Guided by Consideration of Catalyst Stability

Scott D. McCann et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Organic

Biaryl monophosphine ligands in palladium-catalyzed C-N coupling: An updated User's guide

Bryan T. Ingoglia et al.

TETRAHEDRON (2019)

Review Chemistry, Multidisciplinary

The Buchwald-Hartwig Amination After 25 Years

Ruth Dorel et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Inorganic & Nuclear

Evaluating stereoelectronic properties of bulky dialkylterphenyl phosphine ligands

Mario Marin et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

A Highly Active Ylide-Functionalized Phosphine for Palladium-Catalyzed Aminations of Aryl Chlorides

Philip Weber et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Synthesis, Structure and Nickel Carbonyl Complexes of Dialkylterphenyl Phosphines

Mario Marin et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Chemistry, Inorganic & Nuclear

Palladium-mediated intramolecular dearomatization of ligated dialkylterphenyl phosphines

Raquel J. Rama et al.

DALTON TRANSACTIONS (2019)

Review Chemistry, Multidisciplinary

Microkinetic modeling in homogeneous catalysis

Maria Besora et al.

WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL MOLECULAR SCIENCE (2018)

Review Agriculture, Multidisciplinary

Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals

Ponnam Devendar et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2018)

Review Chemistry, Multidisciplinary

Well-defined nickel and palladium precatalysts for cross-coupling

Nilay Hazari et al.

NATURE REVIEWS CHEMISTRY (2017)

Review Chemistry, Multidisciplinary

Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions

Paula Ruiz-Castillo et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Multidisciplinary

Catalytic Arylation Methods. From the Academic Lab to Industrial Processes. By Anthony J. Burke and Carolina Silva Marques.

Marko Hapke

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines

Nathaniel H. Park et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Capture of Reactive Monophosphine-Ligated Palladium(0) Intermediates by Mass Spectrometry

Quling Zheng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis

Paula Ruiz-Castillo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Arylation of Fluoroalkylamines

Andrew T. Brusoe et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Organic

Role of the Base in Buchwald-Hartwig Amination

Ylva Sunesson et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Organic

N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C-C and C-N Cross-Couplings

Nicholas C. Bruno et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Inorganic & Nuclear

Electronic and Structural Effects of Low-Hapticity Coordination of Arene Rings to Transition Metals

Andres Falceto et al.

ORGANOMETALLICS (2014)

Article Chemistry, Multidisciplinary

The Impact of Palladium(II) Reduction Pathways on the Structure and Activity of Palladium(0) Catalysts

Carolyn S. Wei et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Inorganic & Nuclear

Capturing a Ghost. Synthesis and Structural Characterization of Pd(dba)[P(o-Tol)3]2

Brennen A. Harding et al.

ORGANOMETALLICS (2013)

Review Chemistry, Multidisciplinary

The Development of Bulky Palladium NHC Complexes for the Most-Challenging Cross-Coupling Reactions

Cory Valente et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Article Chemistry, Multidisciplinary

Amination with Pd-NHC Complexes: Rate and Computational Studies Involving Substituted Aniline Substrates

Ka Hou Hoi et al.

CHEMISTRY-A EUROPEAN JOURNAL (2012)

Article Chemistry, Multidisciplinary

Investigating the Dearomative Rearrangement of Biaryl Phosphine-Ligated Pd(II) Complexes

Phillip J. Milner et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

A Highly Versatile Catalyst System for the Cross-Coupling of Aryl Chlorides and Amines

Rylan J. Lundgren et al.

CHEMISTRY-A EUROPEAN JOURNAL (2010)

Article Chemistry, Physical

Computational study of PtBu3 as ligand in the palladium-catalysed amination of phenylbromide with morpholine

Claire L. McMullin et al.

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL (2010)

Review Chemistry, Multidisciplinary

Biaryl phosphane ligands in palladium-catalyzed amination

David S. Surry et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Article Chemistry, Multidisciplinary

Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI

Michael G. Organ et al.

CHEMISTRY-A EUROPEAN JOURNAL (2008)

Article Chemistry, Multidisciplinary

Selective palladium-catalyzed arylation of ammonia: Synthesis of anilines as well as symmetrical and unsymmetrical Di- and triarylamines

David S. Surry et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Inorganic & Nuclear

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

Marten Ahlquist et al.

ORGANOMETALLICS (2007)

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)

Article Chemistry, Multidisciplinary

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

N Marion et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

Reevaluation of the mechanism of the amination of aryl halides catalyzed by BINAP-ligated palladium complexes

S Shekhar et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Organic

Density functional theory study of palladium-catalyzed aryl-nitrogen and aryl-oxygen bond formation

TR Cundari et al.

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY (2005)

Article Chemistry, Multidisciplinary

Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure

TE Barder et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Review Chemistry, Multidisciplinary

The development of efficient catalysts for palladium-catalyzed coupling reactions of aryl halides

A Zapf et al.

CHEMICAL COMMUNICATIONS (2005)

Article Chemistry, Multidisciplinary

Highly reactive, general, and long-lived catalysts for coupling heteroaryl and aryl chlorides with primary nitrogen nucleophiles

QL Shen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

Review Chemistry, Multidisciplinary

Monoligated palladium species as catalysts in cross-coupling reactions

U Christmann et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

Review Chemistry, Applied

Palladium-catalyzed C-N and C-O coupling - A practical guide from an industrial vantage point

B Schlummer et al.

ADVANCED SYNTHESIS & CATALYSIS (2004)

Article Chemistry, Multidisciplinary

New ligands for a general palladium-catalyzed amination of aryl and heteroaryl chlorides

F Rataboul et al.

CHEMISTRY-A EUROPEAN JOURNAL (2004)

Article Chemistry, Multidisciplinary

A rationally designed universal catalyst for Suzuki-Miyaura coupling processes

SD Walker et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

Article Chemistry, Multidisciplinary

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

M Yamashita et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Article Chemistry, Multidisciplinary

Mechanistic insights into the Pd(BINAP)-catalyzed amination of aryl bromides: Kinetic studies under synthetically relevant conditions

UK Singh et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

Article Chemistry, Multidisciplinary

A highly active Suzuki catalyst for the synthesis of sterically hindered biaryls: Novel ligand coordination

JJ Yin et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)