Computational study of (PBu3)-Bu-t as ligand in the palladium-catalysed amination of phenylbromide with morpholine

[1]  P. Jessop,et al.  A Kinetics Study of the Oxidative Addition of Bromobenzene to Pd(PCy3)2 (Cy = cyclohexyl) in a Nonpolar Medium: The Influence on Rates of Added PCy3 and Bromide Ion , 2009 .

[2]  S. Buchwald,et al.  Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study. , 2009, Journal of the American Chemical Society.

[3]  Paul M. Murray,et al.  The Newman-Kwart rearrangement of O-aryl thiocarbamates: substantial reduction in reaction temperatures through palladium catalysis. , 2009, Angewandte Chemie.

[4]  B. Yates,et al.  Subtle balance of ligand steric effects in Stille transmetalation. , 2009, Journal of the American Chemical Society.

[5]  Giovanni Occhipinti,et al.  Metal-phosphine bond strengths of the transition metals: a challenge for DFT. , 2009, The journal of physical chemistry. A.

[6]  J. Hartwig,et al.  Effect of ligand steric properties and halide identity on the mechanism for oxidative addition of haloarenes to trialkylphosphine Pd(0) complexes. , 2009, Journal of the American Chemical Society.

[7]  P. V. van Leeuwen,et al.  Bite angle effects of diphosphines in C-C and C-X bond forming cross coupling reactions. , 2009, Chemical Society reviews.

[8]  A. Lledós,et al.  The role of amide ligands in the stabilization of Pd(II) tricoordinated complexes: is the Pd–NR2 bond order single or higher? , 2009 .

[9]  R. Álvarez,et al.  C-C reductive elimination in palladium complexes, and the role of coupling additives. A DFT study supported by experiment. , 2009, Journal of the American Chemical Society.

[10]  G. C. Fu The development of versatile methods for palladium-catalyzed coupling reactions of aryl electrophiles through the use of P(t-Bu)3 and PCy3 as ligands. , 2008, Accounts of chemical research.

[11]  J. Hartwig Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides. , 2008, Accounts of chemical research.

[12]  J. Hartwig Carbon–heteroatom bond formation catalysed by organometallic complexes , 2008, Nature.

[13]  S. Nolan,et al.  Well-defined N-heterocyclic carbenes-palladium(II) precatalysts for cross-coupling reactions. , 2008, Accounts of chemical research.

[14]  S. Buchwald,et al.  Biaryl phosphane ligands in palladium-catalyzed amination. , 2008, Angewandte Chemie.

[15]  Q. Guo,et al.  Theoretical Study on Monoligated Pd-Catalyzed Cross-Coupling Reactions of Aryl Chlorides and Bromides , 2008 .

[16]  P. Andersson,et al.  Combined experimental and theoretical study of the mechanism and enantioselectivity of palladium- catalyzed intermolecular Heck coupling. , 2008, Journal of the American Chemical Society.

[17]  A. Jutand,et al.  Contribution of electrochemistry to organometallic catalysis. , 2008, Chemical reviews.

[18]  T. Ogata,et al.  Highly reactive, general and long-lived catalysts for palladium-catalyzed amination of heteroaryl and aryl chlorides, bromides, and iodides: scope and structure-activity relationships. , 2008, Journal of the American Chemical Society.

[19]  D. Blackmond,et al.  Mechanistic Inferences Derived from Competitive Catalytic Reactions: Pd(binap)‐Catalyzed Amination of Aryl Halides , 2008 .

[20]  Jeremy N. Harvey,et al.  Computational descriptors for chelating P,P- and P,N-donor ligands , 2008 .

[21]  J. Hartwig,et al.  Autocatalytic oxidative addition of PhBr to Pd(PtBu3)2 via Pd(PtBu3)2(H)(Br). , 2008, Journal of the American Chemical Society.

[22]  H. Hoefsloot,et al.  Insights into Sonogashira cross-coupling by high-throughput kinetics and descriptor modeling. , 2008, Chemistry.

[23]  M. Beller,et al.  Synthesis and Crystal Structure of Palladium(0) and Arylpalladium(II) Bromide Complexes of CataCXium A , 2008 .

[24]  S. Buchwald,et al.  Electronic effects on the selectivity of pd-catalyzed C-N bond-forming reactions using biarylphosphine ligands: the competitive roles of amine binding and acidity. , 2007, Angewandte Chemie.

[25]  S. Buchwald,et al.  Insights into amine binding to biaryl phosphine palladium oxidative addition complexes and reductive elimination from biaryl phosphine arylpalladium amido complexes via density functional theory. , 2007, Journal of the American Chemical Society.

[26]  M. C. Baird,et al.  Optimization of Procedures for the Syntheses of Bisphosphinepalladium(0) Precursors for Suzuki−Miyaura and Similar Cross-Coupling Catalysis: Identification of 3:1 Coordination Compounds in Catalyst Mixtures Containing Pd(0), PCy3, and/or PMeBut2 , 2007 .

[27]  Alireza Ariafard,et al.  Theoretical studies of the oxidative addition of PhBr to Pd(PX3)2 and Pd(X2PCH2CH2PX2) (X = Me, H, Cl) , 2007 .

[28]  R. Jordan Amination of Aryl Halides: Quantitative Assessment of Stoichiometric and Catalytic Kinetic Studies , 2007 .

[29]  M. Organ,et al.  Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions--a synthetic chemist's perspective. , 2007, Angewandte Chemie.

[30]  S. Buchwald,et al.  Structural Insights into Active Catalyst Structures and Oxidative Addition to (Biaryl)phosphine−Palladium Complexes via Density Functional Theory and Experimental Studies , 2007 .

[31]  J. Hartwig Electronic effects on reductive elimination to form carbon-carbon and carbon-heteroatom bonds from palladium(II) complexes. , 2007, Inorganic chemistry.

[32]  P. Norrby,et al.  Oxidative Addition of Aryl Chlorides to Monoligated Palladium(0): A DFT-SCRF Study , 2007 .

[33]  S. Shekhar,et al.  Effects of Bases and Halides on the Amination of Chloroarenes Catalyzed by Pd(PtBu3)2. , 2007, Organometallics.

[34]  G. Mignani,et al.  Selected patented cross-coupling reaction technologies. , 2006, Chemical reviews.

[35]  Gregori Ujaque,et al.  A DFT Study of the Full Catalytic Cycle of the Suzuki−Miyaura Cross-Coupling on a Model System , 2006 .

[36]  D. Dixon,et al.  Bulky alkylphosphines with neopentyl substituents as ligands in the amination of aryl bromides and chlorides. , 2006, The Journal of organic chemistry.

[37]  D. Pantazis,et al.  Experimental and theoretical investigations of new dinuclear palladium complexes as precatalysts for the amination of aryl chlorides. , 2006, Journal of the American Chemical Society.

[38]  D. Tanner,et al.  Theoretical Evidence for Low-Ligated Palladium(0): [Pd−L] as the Active Species in Oxidative Addition Reactions , 2006 .

[39]  S. Buchwald,et al.  Reevaluation of the mechanism of the amination of aryl halides catalyzed by BINAP-ligated palladium complexes. , 2006, Journal of the American Chemical Society.

[40]  S. Shaik,et al.  A combined kinetic-quantum mechanical model for assessment of catalytic cycles: application to cross-coupling and Heck reactions. , 2006, Journal of the American Chemical Society.

[41]  S. Buchwald,et al.  Evidence for the formation and structure of palladacycles during Pd-catalyzed C-N bond formation with catalysts derived from bulky monophosphinobiaryl ligands. , 2006, Angewandte Chemie.

[42]  W. Thiel,et al.  Palladium Monophosphine Intermediates in Catalytic Cross-Coupling Reactions: A DFT Study , 2006 .

[43]  S. Buchwald,et al.  Industrial-Scale Palladium-Catalyzed Coupling of Aryl Halides and Amines –A Personal Account , 2006 .

[44]  R. Lonsdale,et al.  Oxidative addition of aryl chlorides to palladium N-heterocyclic carbene complexes and their role in catalytic arylamination , 2005 .

[45]  C. Bo,et al.  Reductive Elimination of Organic Molecules from Palladium−Diphosphine Complexes , 2005 .

[46]  T. Cundari,et al.  Density functional theory study of palladium‐catalyzed aryl‐nitrogen and aryl‐oxygen bond formation , 2005 .

[47]  J. Hartwig,et al.  Distinct mechanisms for the oxidative addition of chloro-, bromo-, and iodoarenes to a bisphosphine palladium(0) complex with hindered ligands. , 2005, Journal of the American Chemical Society.

[48]  S. Shaik,et al.  What makes for a good catalytic cycle? A theoretical study of the role of an anionic palladium(0) complex in the cross-coupling of an aryl halide with an anionic nucleophile , 2005 .

[49]  S. Buchwald,et al.  Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure. , 2005, Journal of the American Chemical Society.

[50]  D. Dixon,et al.  Experimental and Computational Study of Steric and Electronic Effects on the Coordination of Bulky, Water-Soluble Alkylphosphines to Palladium under Reducing Conditions: Correlation to Catalytic Activity , 2005 .

[51]  R. Vilar,et al.  Monoligated palladium species as catalysts in cross-coupling reactions. , 2005, Angewandte Chemie.

[52]  A. Orpen,et al.  Development of a ligand knowledge base, part 1: computational descriptors for phosphorus donor ligands. , 2005, Chemistry.

[53]  U. Scholz,et al.  Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point† , 2004 .

[54]  V. Farina High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview , 2004 .

[55]  S. Shekhar,et al.  Distinct electronic effects on reductive eliminations of symmetrical and unsymmetrical bis-aryl platinum complexes. , 2004, Journal of the American Chemical Society.

[56]  S. Shaik,et al.  Active anionic zero-valent palladium catalysts: characterization by density functional calculations. , 2004, Chemistry.

[57]  J. Hartwig,et al.  Carbon−Carbon Bond-Forming Reductive Elimination from Arylpalladium Complexes Containing Functionalized Alkyl Groups. Influence of Ligand Steric and Electronic Properties on Structure, Stability, and Reactivity , 2004 .

[58]  H. Senn,et al.  Oxidative Addition of Aryl Halides to Palladium(0) Complexes: A Density-Functional Study Including Solvation , 2004 .

[59]  M. Yamashita,et al.  Synthesis, structure, and reductive elimination chemistry of three-coordinate arylpalladium amido complexes. , 2004, Journal of the American Chemical Society.

[60]  C. Incarvito,et al.  Synthesis, structure, theoretical studies, and Ligand exchange reactions of monomeric, T-shaped arylpalladium(II) halide complexes with an additional, weak agostic interaction. , 2004, Journal of the American Chemical Society.

[61]  M. Yamashita,et al.  Trans influence on the rate of reductive elimination. Reductive elimination of amines from isomeric arylpalladium amides with unsymmetrical coordination spheres. , 2003, Journal of the American Chemical Society.

[62]  T. Cundari,et al.  ONIOM study of the active species in Pd–phosphine catalyzed coupling reactions , 2003 .

[63]  S. Stauffer,et al.  Fluorescence resonance energy transfer (FRET) as a high-throughput assay for coupling reactions. Arylation of amines as a case study. , 2003, Journal of the American Chemical Society.

[64]  S. Grimme Improved second-order Møller–Plesset perturbation theory by separate scaling of parallel- and antiparallel-spin pair correlation energies , 2003 .

[65]  J. Verkade,et al.  P(i-BuNCH2CH2)3N: an effective ligand in the palladium-catalyzed amination of aryl bromides and iodides. , 2003, The Journal of organic chemistry.

[66]  J. Hartwig,et al.  Unparalleled rates for the activation of aryl chlorides and bromides: coupling with amines and boronic acids in minutes at room temperature. , 2002, Angewandte Chemie.

[67]  G. C. Fu,et al.  Palladium-catalyzed coupling reactions of aryl chlorides. , 2002, Angewandte Chemie.

[68]  M. Bühl,et al.  Synthesis, characterization, and reactivity of monomeric, arylpalladium halide complexes with a hindered phosphine as the only dative ligand. , 2002, Journal of the American Chemical Society.

[69]  M. Beller,et al.  A new improved catalyst for the palladium-catalyzed amination of aryl chlorides , 2002 .

[70]  S. Stauffer,et al.  Screening of homogeneous catalysts by fluorescence resonance energy transfer. Identification of catalysts for room-temperature Heck reactions. , 2001, Journal of the American Chemical Society.

[71]  Jan M. L. Martin,et al.  Correlation consistent valence basis sets for use with the Stuttgart–Dresden–Bonn relativistic effective core potentials: The atoms Ga–Kr and In–Xe , 2000, physics/0011030.

[72]  Paul J. Fagan,et al.  Using Intelligent/Random Library Screening To Design Focused Libraries for the Optimization of Homogeneous Catalysts: Ullmann Ether Formation , 2000 .

[73]  G. C. Fu,et al.  Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions , 2000 .

[74]  C. Amatore,et al.  Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions. , 2000, Accounts of chemical research.

[75]  S. Buchwald,et al.  Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates. , 2000, The Journal of organic chemistry.

[76]  P. Knowles,et al.  Erratum: “Coupled cluster theory for high spin, open shell reference wave functions” [ J. Chem. Phys. 99, 5219 (1993)] , 2000 .

[77]  J. Hartwig Approaches to catalyst discovery. New carbon–heteroatom and carbon–carbon bond formation , 1999 .

[78]  J. Hartwig,et al.  Room-Temperature Palladium-Catalyzed Amination of Aryl Bromides and Chlorides and Extended Scope of Aromatic C-N Bond Formation with a Commercial Ligand. , 1999, The Journal of organic chemistry.

[79]  J. Hartwig Carbon−Heteroatom Bond-Forming Reductive Eliminations of Amines, Ethers, and Sulfides , 1998 .

[80]  N. Rösch,et al.  On C−C Coupling by Carbene-Stabilized Palladium Catalysts: A Density Functional Study of the Heck Reaction , 1998 .

[81]  John F. Hartwig,et al.  A Second-Generation Catalyst for Aryl Halide Amination: Mixed Secondary Amines from Aryl Halides and Primary Amines Catalyzed by (DPPF)PdCl2 , 1996 .

[82]  B. Honig,et al.  New Model for Calculation of Solvation Free Energies: Correction of Self-Consistent Reaction Field Continuum Dielectric Theory for Short-Range Hydrogen-Bonding Effects , 1996 .

[83]  D. Barañano,et al.  Influences on the Relative Rates for C−N Bond-Forming Reductive Elimination and β-Hydrogen Elimination of Amides. A Case Study on the Origins of Competing Reduction in the Palladium-Catalyzed Amination of Aryl Halides , 1996 .

[84]  Thom H. Dunning,et al.  Gaussian basis sets for use in correlated molecular calculations. V. Core-valence basis sets for boron through neon , 1995 .

[85]  J. Hartwig,et al.  Structural Characterization and Simple Synthesis of {Pd[P(o-Tol)3]2}. Spectroscopic Study and Structural Characterization of the Dimeric Palladium(II) Complexes Obtained by Oxidative Addition of Aryl Bromides and Their Reactivity with Amines , 1995 .

[86]  B. Honig,et al.  Accurate First Principles Calculation of Molecular Charge Distributions and Solvation Energies from Ab Initio Quantum Mechanics and Continuum Dielectric Theory , 1994 .

[87]  Martin Head-Gordon,et al.  Analytic MP2 frequencies without fifth-order storage. Theory and application to bifurcated hydrogen bonds in the water hexamer , 1994 .

[88]  Hans-Joachim Werner,et al.  Coupled cluster theory for high spin, open shell reference wave functions , 1993 .

[89]  Jürgen Gauss,et al.  Coupled‐cluster methods with noniterative triple excitations for restricted open‐shell Hartree–Fock and other general single determinant reference functions. Energies and analytical gradients , 1993 .

[90]  A. Becke Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[91]  Michael J. Frisch,et al.  A direct MP2 gradient method , 1990 .

[92]  Michael J. Frisch,et al.  Semi-direct algorithms for the MP2 energy and gradient , 1990 .

[93]  G. Scuseria,et al.  Is coupled cluster singles and doubles (CCSD) more computationally intensive than quadratic configuration interaction (QCISD) , 1989 .

[94]  Svein Saebo,et al.  Avoiding the integral storage bottleneck in LCAO calculations of electron correlation , 1989 .

[95]  Michael J. Frisch,et al.  MP2 energy evaluation by direct methods , 1988 .

[96]  Curtis L. Janssen,et al.  An efficient reformulation of the closed‐shell coupled cluster single and double excitation (CCSD) equations , 1988 .

[97]  A. Becke,et al.  Density-functional exchange-energy approximation with correct asymptotic behavior. , 1988, Physical review. A, General physics.

[98]  Martin Head-Gordon,et al.  Quadratic configuration interaction. A general technique for determining electron correlation energies , 1987 .

[99]  Mohan,et al.  Erratum: Electronic response function of coupled chains of finite radius , 1986, Physical review. B, Condensed matter.

[100]  J. Perdew,et al.  Density-functional approximation for the correlation energy of the inhomogeneous electron gas. , 1986, Physical review. B, Condensed matter.

[101]  R. Bartlett,et al.  A full coupled‐cluster singles and doubles model: The inclusion of disconnected triples , 1982 .

[102]  S. H. Vosko,et al.  Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis , 1980 .

[103]  John C. Slater,et al.  Quantum Theory of Molecules and Solids Vol. 4: The Self‐Consistent Field for Molecules and Solids , 1974 .