A rational pre-catalyst design for bis-phosphine mono-oxide palladium catalyzed reactions

Detailed mechanistic studies of a Pd-catalyzed asymmetric C–N coupling led to a rational design of a new series of bis-phosphine mono-oxides ligated Pd(ii) pre-catalysts that allow for reliable and complete catalyst activation.

[1]  Rebecca T. Ruck,et al.  Discovery of Ruzasvir (MK-8408): A Potent, Pan-Genotype HCV NS5A Inhibitor with Optimized Activity against Common Resistance-Associated Polymorphisms. , 2017, Journal of medicinal chemistry.

[2]  V. M. Dong,et al.  Diastereodivergent Construction of Bicyclic γ-Lactones via Enantioselective Ketone Hydroacylation. , 2016, Journal of the American Chemical Society.

[3]  C. Mazet,et al.  Palladium-Catalyzed Enantioselective Intermolecular Carboetherification of Dihydrofurans. , 2016, Journal of the American Chemical Society.

[4]  Yining Ji,et al.  Enantioselective Synthesis of Hemiaminals via Pd-Catalyzed C-N Coupling with Chiral Bisphosphine Mono-oxides. , 2015, Journal of the American Chemical Society.

[5]  Michael Schmidt,et al.  Mono-Oxidation of Bidentate Bis-phosphines in Catalyst Activation: Kinetic and Mechanistic Studies of a Pd/Xantphos-Catalyzed C-H Functionalization. , 2015, Journal of the American Chemical Society.

[6]  D. Blackmond,et al.  Kinetic Profiling of Catalytic Organic Reactions as a Mechanistic Tool. , 2015, Journal of the American Chemical Society.

[7]  A. Doyle,et al.  A modular, air-stable nickel precatalyst. , 2015, Organic letters.

[8]  Guolan Xiao,et al.  Efficient synthesis of sterically hindered arenes bearing acyclic secondary alkyl groups by Suzuki-Miyaura cross-couplings. , 2015, Angewandte Chemie.

[9]  S. Gilbertson,et al.  [4+2+2] Cycloaddition catalyzed by a new cationic rhodium-bisphosphine monooxide complex. , 2014, Chemical communications.

[10]  G. Lloyd‐Jones,et al.  Selection of boron reagents for Suzuki-Miyaura coupling. , 2014, Chemical Society reviews.

[11]  J. Zhou,et al.  Asymmetric intermolecular Heck reaction of aryl halides. , 2014, Journal of the American Chemical Society.

[12]  M. Oestreich,et al.  Hemilabile BINAP(O) as a Chiral Ligand in Desymmetrizing Mizoroki–Heck Cyclizations , 2012 .

[13]  K. Nozaki,et al.  Synthesis of functional polyolefins using cationic bisphosphine monoxide-palladium complexes. , 2012, Journal of the American Chemical Society.

[14]  J. Hartwig,et al.  On the interpretation of deuterium kinetic isotope effects in C-H bond functionalizations by transition-metal complexes. , 2012, Angewandte Chemie.

[15]  M. Oestreich,et al.  BINAP versus BINAP(O) in asymmetric intermolecular Mizoroki-Heck reactions: substantial effects on selectivities. , 2011, Chemistry.

[16]  I. Davies,et al.  Preparative scale synthesis of the biaryl core of anacetrapib via a ruthenium-catalyzed direct arylation reaction: unexpected effect of solvent impurity on the arylation reaction. , 2011, The Journal of organic chemistry.

[17]  Yongxin Li,et al.  Chiral palladacycle promoted asymmetric synthesis of functionalized bis-phosphine monoxide ligand , 2011 .

[18]  B. Pugin,et al.  Chiral mixed secondary phosphine-oxide-phosphines: high-performing and easily accessible ligands for asymmetric hydrogenation. , 2010, Angewandte Chemie.

[19]  C. Cramer,et al.  Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. , 2009, The journal of physical chemistry. B.

[20]  A. Charette,et al.  Probing the importance of the hemilabile site of bis(phosphine) monoxide ligands in the copper-catalyzed addition of diethylzinc to N-phosphinoylimines: discovery of new effective chiral ligands. , 2008, The Journal of organic chemistry.

[21]  Masayuki Wakioka,et al.  Reaction of trans-Pd(styryl)Br(PMePh2)(2) with styryl bromide affording 1,4-diphenylbutadiene. An unexpected homocoupling process induced by P-C reductive elimination , 2008 .

[22]  D. Truhlar,et al.  The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals , 2008 .

[23]  A. Côté,et al.  Application of the chiral bis(phosphine) monoxide ligand to catalytic enantioselective addition of dialkylzinc reagents to beta-nitroalkenes. , 2007, Organic letters.

[24]  P. Sgarbossa,et al.  Bis-phosphine monoxide platinum(II) and palladium(II) cationic complexes as Lewis acid catalysts in Diels–Alder and sulfoxidation reactions , 2006 .

[25]  Alan S. Futran,et al.  Investigations of Pd-catalyzed ArX coupling reactions informed by reaction progress kinetic analysis. , 2006, The Journal of organic chemistry.

[26]  S. Tee,et al.  Chiral metal template induced asymmetric synthesis of a mixed phosphine-phosphine oxide ligand , 2005 .

[27]  D. Blackmond Reaction progress kinetic analysis: a powerful methodology for mechanistic studies of complex catalytic reactions. , 2005, Angewandte Chemie.

[28]  A. Côté,et al.  Evidence for the structure of the enantioactive ligand in the phosphine-copper-catalyzed addition of diorganozinc reagents to imines. , 2004, Angewandte Chemie.

[29]  V. Grushin Mixed phosphine--phosphine oxide ligands. , 2004, Chemical reviews.

[30]  A. Côté,et al.  Asymmetric, catalytic synthesis of alpha-chiral amines using a novel bis(phosphine) monoxide chiral ligand. , 2003, Journal of the American Chemical Society.

[31]  W. Marshall,et al.  Palladium(II) and Palladium(0) Complexes of BINAP(O) (2-(Diphenylphosphino)-2‘-(diphenylphosphinyl)-1,1‘-binaphthyl) , 2003 .

[32]  V. Grushin Synthesis of Hemilabile Phosphine−Phosphine Oxide Ligands via the Highly Selective Pd-Catalyzed Mono-oxidation of Bidentate Phosphines: Scope, Limitations, and Mechanism , 2001 .

[33]  C. Amatore,et al.  Formation of Palladium(0) Complexes from Pd(OAc)2 and a Bidentate Phosphine Ligand (dppp) and Their Reactivity in Oxidative Addition , 2001 .

[34]  B. Grimmond,et al.  An application of electronic asymmetry to highly enantioselective catalytic Diels-Alder reactions. , 2001, Journal of the American Chemical Society.

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

[36]  V. Grushin Catalysis for Catalysis: Synthesis of Mixed Phosphine−Phosphine Oxide Ligands via Highly Selective, Pd-Catalyzed Monooxidation of Bidentate Phosphines , 1999 .

[37]  L. Kollár,et al.  NMR investigation of Pd(II)–Pd(0) reduction in the presence of mono- and ditertiary phosphines , 1999 .

[38]  M. Manassero,et al.  2-Diphenylphosphino-2′-diphenylphosphinyl-1,1′-binaphthalene (BINAPO), an axially chiral heterobidentate ligand for enantioselective catalysis , 1998 .

[39]  I. Shimizu,et al.  Enantioselective elimination reaction of a 6,6-membered bicyclic allylic carbonate. Importance of chirality reversal depending on the palladium-chiral phosphine ratio , 1996 .

[40]  C. Amatore,et al.  Evidence for the Ligation of Palladium(0) Complexes by Acetate Ions: Consequences on the Mechanism of Their Oxidative Addition with Phenyl Iodide and PhPd(OAc)(PPh3)2 as Intermediate in the Heck Reaction , 1995 .

[41]  C. Amatore,et al.  Rates and Mechanism of the Formation of Zerovalent Palladium Complexes from Mixtures of Pd(OAc)2 and Tertiary Phosphines and Their Reactivity in Oxidative Additions , 1995 .

[42]  H. Alper,et al.  Dichlorobis(tricyclohexylphosphine)palladium(II): Synthesis and Crystal Structure. An Exceptionally Simple and Efficient Preparation of Bis(tricyclohexylphosphine)palladium(0) , 1994 .

[43]  K. Nozaki,et al.  Cationic BINAP-Ru(II) Halide Complexes: Highly Efficient Catalysts for Stereoselective Asymmetric Hydrogenation of .alpha.- and .beta.-Functionalized Ketones , 1994 .

[44]  Joel T. Mague,et al.  Synthesis, structure, and unusual reactivity of a d10-d10 palladium(0) dimer , 1993 .

[45]  H. Alper,et al.  Alkali-induced disproportionation of palladium(II) tertiary phosphine complexes, [L2PdCl2], to LO and palladium(O). Key intermediates in the biphasic carbonylation of ArX catalyzed by [L2PdCl2] , 1993 .

[46]  J. Tsuji,et al.  Highly active Pd(O) catalyst from Pd(OAc)2Bu3P combination in untapped 1:1 ratio: Preparation, reactivity, and 31P-NMR , 1993 .

[47]  F. Ozawa,et al.  Generation of Tertiary Phosphine-Coordinated Pd(0) Species from Pd(OAc)2 in the Catalytic Heck Reaction , 1992 .

[48]  C. Amatore,et al.  Evidence of the formation of zerovalent palladium from Pd(OAc)2 and triphenylphosphine , 1992 .

[49]  P. Fitton,et al.  The addition of aryl halides to tetrakis(triphenylphosphine)palladium(0) , 1971 .

[50]  Donald G. Truhlar,et al.  Theoretical Chemistry Accounts , 2001 .

[51]  M. Scarsella,et al.  A rapid and convenient synthesis of tetrakis(triphenylphosphine)palladium(O) and -platinum(O) complexes by phase-transfer catalysis , 1991 .

[52]  A. Neuhaus Book Review: Kristallisation. Grundlagen und Technik. (Fundamentals and Techniques of Crystallization). By G. Matz , 1970 .