메뉴 건너뛰기




Volumn 38, Issue , 2012, Pages 65-94

Computational insights into palladium-mediated allylic substitution reactions

Author keywords

Density functional theory; Molecular mechanics; Palladium mediated allylation; Quantum mechanics; Reaction mechanisms

Indexed keywords


EID: 84962449926     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/3418_2011_8     Document Type: Article
Times cited : (26)

References (88)
  • 2
    • 0042379988 scopus 로고    scopus 로고
    • Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis
    • Trost BM, Crawley ML (2003) Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis. Chem Rev 103:2921
    • (2003) Chem Rev , vol.103 , pp. 2921
    • Trost, B.M.1    Crawley, M.L.2
  • 3
    • 0001758225 scopus 로고    scopus 로고
    • Theoretical studies in palladium and platinum molecular chemistry
    • Dedieu A (2000) Theoretical studies in palladium and platinum molecular chemistry. Chem Rev 100:543
    • (2000) Chem Rev , vol.100 , pp. 543
    • Dedieu, A.1
  • 6
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. 3. The role of exact exchange
    • Becke AD (1993) Density-functional thermochemistry. 3. The role of exact exchange. J Chem Phys 98:5648
    • (1993) J Chem Phys , vol.98 , pp. 5648
    • Becke, A.D.1
  • 7
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density
    • Lee CT, Yang WT, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density. Phys Rev B 37:785
    • (1988) Phys Rev B. , vol.37 , pp. 785
    • Lee, C.T.1    Yang, W.T.2    Parr, R.G.3
  • 8
    • 33751157732 scopus 로고
    • Ab-initio calculation of vibrational absorption and circular-dichroism spectra using density-functional force-fields
    • Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ (1994) Ab-initio calculation of vibrational absorption and circular-dichroism spectra using density-functional force-fields. J Phys Chem 98:11623
    • (1994) J Phys Chem , vol.98 , pp. 11623
    • Stephens, P.J.1    Devlin, F.J.2    Chabalowski, C.F.3    Frisch, M.J.4
  • 9
    • 4043164887 scopus 로고    scopus 로고
    • Accurate description of van der Waals complexes by density functional theory including empirical corrections
    • Grimme S (2004) Accurate description of van der Waals complexes by density functional theory including empirical corrections. J Comput Chem 25:1463
    • (2004) J Comput Chem , vol.25 , pp. 1463
    • Grimme, S.1
  • 10
    • 43049141516 scopus 로고    scopus 로고
    • 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
    • Zhao Y, Truhlar DG (2008) 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. Theor Chem Acc 120:215
    • (2008) Theor Chem Acc , vol.120 , pp. 215
    • Zhao, Y.1    Truhlar, D.G.2
  • 11
    • 77954175093 scopus 로고    scopus 로고
    • Binding energy of d(10) transition metals to alkenes by wave function theory and density functional theory
    • Averkiev BB, Zhao Y, Truhlar DG (2010) Binding energy of d(10) transition metals to alkenes by wave function theory and density functional theory. J Mol Catal A-Chem 324:80
    • (2010) J Mol Catal A-Chem 324 , pp. 80
    • Averkiev, B.B.1    Zhao, Y.2    Truhlar, D.G.3
  • 12
    • 77951680464 scopus 로고    scopus 로고
    • A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu
    • Grimme S, Antony J, Ehrlich S, Krieg H (2010) A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys 132:154104
    • (2010) J Chem Phys , vol.132 , pp. 154104
    • Grimme, S.1    Antony, J.2    Ehrlich, S.3    Krieg, H.4
  • 13
    • 70349232323 scopus 로고    scopus 로고
    • Application of dispersion-corrected density functional theory
    • Nilsson Lill SO (2009) Application of dispersion-corrected density functional theory. J Phys Chem A 113:10321
    • (2009) J Phys Chem A. , vol.113 , pp. 10321
    • Nilsson Lill, S.O.1
  • 14
    • 84946893847 scopus 로고
    • Electrostatic interaction of a solute with a continuum- A direct utilization of abinitio molecular potentials for the prevision of solvent effects
    • Miertus S, Scrocco E, Tomasi J (1981) Electrostatic interaction of a solute with a continuum - a direct utilization of abinitio molecular potentials for the prevision of solvent effects. Chem Phys 55:117
    • (1981) Chem Phys , vol.55 , pp. 117
    • Miertus, S.1    Scrocco, E.2    Tomasi, J.3
  • 15
    • 84986435825 scopus 로고
    • Remarks on the use of the apparent surface-charges (ASC) methods in solvation problems - iterative versus matrix-inversion procedures and the renormalization of the apparent charges
    • Cammi R, Tomasi J (1995) Remarks on the use of the apparent surface-charges (ASC) methods in solvation problems - iterative versus matrix-inversion procedures and the renormalization of the apparent charges. J Comput Chem 16:1449
    • (1995) J Comput Chem , vol.16 , pp. 1449
    • Cammi, R.1    Tomasi, J.2
  • 16
    • 0032988966 scopus 로고    scopus 로고
    • A solvated transition state for the nucleophilic attack on cationic Z3-allylpalladium complexes
    • Hagelin H, Akermark B, Norrby PO (1999) A solvated transition state for the nucleophilic attack on cationic Z3-allylpalladium complexes. Chem-Eur J 5:902
    • (1999) Chem-Eur J. , vol.5 , pp. 902
    • Hagelin, H.1    Akermark, B.2    Norrby, P.O.3
  • 19
    • 0006501280 scopus 로고
    • Conformations of (Z3-Cyclohexenyl)palladium systems - A molecular mechanics (MM2) study
    • Akermark B, Oslob JD, Norrby PO (1995) Conformations of (Z3-Cyclohexenyl)palladium systems - a molecular mechanics (MM2) study. Organometallics 14:1688
    • (1995) Organometallics , vol.14 , pp. 1688
    • Akermark, B.1    Oslob, J.D.2    Norrby, P.O.3
  • 20
    • 0000090158 scopus 로고    scopus 로고
    • Molecular mechanics (MM3*) force field parameters for calculations on palladium olefin complexes with phosphorus ligands
    • Hagelin H, Svensson M, Akermark B, Norrby PO (1999) Molecular mechanics (MM3*) force field parameters for calculations on palladium olefin complexes with phosphorus ligands. Organometallics 18:4574
    • (1999) Organometallics , vol.18 , pp. 4574
    • Hagelin, H.1    Svensson, M.2    Akermark, B.3    Norrby, P.O.4
  • 21
    • 0000419724 scopus 로고    scopus 로고
    • New molecular mechanics (MM3*) force field parameters for calculations on (Z3-allyl)palladium complexes with nitrogen and phosphorus ligands
    • Hagelin H, Akermark B, Norrby PO (1999) New molecular mechanics (MM3*) force field parameters for calculations on (Z3-allyl)palladium complexes with nitrogen and phosphorus ligands. Organometallics 18:2884
    • (1999) Organometallics , vol.18 , pp. 2884
    • Hagelin, H.1    Akermark, B.2    Norrby, P.O.3
  • 22
    • 0002103621 scopus 로고
    • X-raydiffraction, multidimensional NMR-spectroscopy, and MM2* calculations on chiral allyl complexes of palladium(I.I.)
    • Pregosin PS, Ruegger H, Salzmann R, Albinati A, Lianza F, Kunz RW (1994) X-raydiffraction, multidimensional NMR-spectroscopy, and MM2* calculations on chiral allyl complexes of palladium(II). Organometallics 13:83
    • (1994) Organometallics , vol.13 , pp. 83
    • Pregosin, P.S.1    Ruegger, H.2    Salzmann, R.3    Albinati, A.4    Lianza, F.5    Kunz, R.W.6
  • 23
    • 0000512852 scopus 로고    scopus 로고
    • Effects of the ancillary ligands on palladium-carbon bonding in (Z3-allyl) palladium complexes Implications for nucleophilic attack at the allylic carbons
    • Szabo KJ (1996) Effects of the ancillary ligands on palladium-carbon bonding in (Z3-allyl) palladium complexes. Implications for nucleophilic attack at the allylic carbons. Organometallics 15:1128
    • (1996) Organometallics , vol.15 , pp. 1128
    • Szabo, K.J.1
  • 24
    • 0001273646 scopus 로고    scopus 로고
    • Density functional study on the regioselectivity of nucleophilic attack in 1,3-disubstituted (diphosphino) (Z3-allyl)palladium cations
    • Branchadell V, Moreno-Manas M, Pajuelo F, Pleixats R (1999) Density functional study on the regioselectivity of nucleophilic attack in 1,3-disubstituted (diphosphino) (Z3-allyl)palladium cations. Organometallics 18:4934
    • (1999) Organometallics , vol.18 , pp. 4934
    • Branchadell, V.1    Moreno-Manas, M.2    Pajuelo, F.3    Pleixats, R.4
  • 25
    • 0034228887 scopus 로고    scopus 로고
    • Regioselectivity of the nucleophilic addition to (Z3-allyl) palladium complexes A theoretical study
    • Delbecq F, Lapouge C (2000) Regioselectivity of the nucleophilic addition to (Z3-allyl) palladium complexes. A theoretical study. Organometallics 19:2716
    • (2000) Organometallics , vol.19 , pp. 2716
    • Delbecq, F.1    Lapouge, C.2
  • 26
    • 0035914628 scopus 로고    scopus 로고
    • (Phosphanyloxazoline palladium complexes, part I: (Z3-1,3-dialkylallyl) (phosphanyloxazoline)palladium complexes: X-ray crystallographic studies, NMR investigations, and quantum-chemical calculations
    • Kollmar M, Goldfuss B, Reggelin M, Rominger F, Helmchen G (2001) (Phosphanyloxazoline) palladium complexes, part I: (Z3-1,3-dialkylallyl) (phosphanyloxazoline)palladium complexes: X-ray crystallographic studies, NMR investigations, and quantum-chemical calculations. Chem-Eur J 7:4913
    • (2001) Chem-Eur J. , vol.7 , pp. 4913
    • Kollmar, M.1    Goldfuss, B.2    Reggelin, M.3    Rominger, F.4    Helmchen, G.5
  • 27
    • 0037101666 scopus 로고    scopus 로고
    • (Phosphanyloxazoline palladium complexes, part II - (Z3-Phenylallyl) (phosphanyloxazoline)palladium complexes: X-ray crystallographic studies, NMR investigations, and ab initio/DFT calculations
    • Kollmar M, Steinhagen H, Janssen JP, Goldfuss B, Malinovskaya SA, Vazquez J, Rominger F, Helmchen G (2002) (Phosphanyloxazoline)palladium complexes, part II - (Z3-Phenylallyl) (phosphanyloxazoline)palladium complexes: X-ray crystallographic studies, NMR investigations, and ab initio/DFT calculations. Chem-Eur J 8:3103
    • (2002) Chem-Eur J. , vol.8 , pp. 3103
    • Kollmar, M.1    Steinhagen, H.2    Janssen, J.P.3    Goldfuss, B.4    Malinovskaya, S.A.5    Vazquez, J.6    Rominger, F.7    Helmchen, G.8
  • 30
    • 0001224182 scopus 로고    scopus 로고
    • Geometries, bonding nature, and relative stabilities of dinuclear palladium(I) pi-allyl and mononuclear palladium(II) pi-allyl complexes A theoretical study
    • Sakaki S, Takeuchi K, Sugimoto M, Kurosawa H (1997) Geometries, bonding nature, and relative stabilities of dinuclear palladium(I) pi-allyl and mononuclear palladium(II) pi-allyl complexes. A theoretical study. Organometallics 16:2995
    • (1997) Organometallics , vol.16 , pp. 2995
    • Sakaki, S.1    Takeuchi, K.2    Sugimoto, M.3    Kurosawa, H.4
  • 31
    • 0035249426 scopus 로고    scopus 로고
    • UV-photoelectron spectra of [M(Z3-C3H5)(2)] (M = Ni, Pd, Pt) revisited: A quasi-relativistic density functional study
    • Casarin M, Pandolfo L, Vittadini A (2001) UV-photoelectron spectra of [M(Z3-C3H5)(2)] (M = Ni, Pd, Pt) revisited: A quasi-relativistic density functional study. Organometallics 20:754
    • (2001) Organometallics , vol.20 , pp. 754
    • Casarin, M.1    Pandolfo, L.2    Vittadini, A.3
  • 32
    • 0034388603 scopus 로고    scopus 로고
    • Umpolung of the allylpalladium reactivity: Mechanism and regioselectivity of the electrophilic attack on bis-allylpalladium complexes formed in palladium-catalyzed transformations
    • Szabo KJ (2000) Umpolung of the allylpalladium reactivity: Mechanism and regioselectivity of the electrophilic attack on bis-allylpalladium complexes formed in palladium-catalyzed transformations. Chem-Eur J 6:4413
    • (2000) Chem-Eur J. , vol.6 , pp. 4413
    • Szabo, K.J.1
  • 33
    • 84989103174 scopus 로고
    • 2D-NOESY studies on [Pd- Z3- C10h15)((R)(+)-Binap)]+ defining the relative spatial orientation of the phenyl and p-allyl moieties
    • Ruegger H, Kunz RW, Ammann CJ, Pregosin PS (1991) 2D-NOESY studies on [Pd- Z3- C10h15)((R)(+)-Binap)]+ defining the relative spatial orientation of the phenyl and p-allyl moieties. Magn Reson Chem 29:197
    • (1991) Magn Reson Chem , vol.29 , pp. 197
    • Ruegger, H.1    Kunz, R.W.2    Ammann, C.J.3    Pregosin, P.S.4
  • 34
    • 0000071085 scopus 로고
    • Chemistry of Pdii complexes containing both Binap (2'2'- bis(diphenylphosphino)binaphthyl) and a Z3-pinene or Z3-allyl ligand - NMR-studies on [Pd(Z3-C10H15)(S(-)Binap)] (CF3SO3) - The crystal-structure of [Pd(Z3-C10H15)(4,4'-dimethylbipyridine)](CF3SO3
    • Ammann CJ, Pregosin PS, Ruegger H, Albinati A, Lianza F, Kunz RW (1992) Chemistry of Pdii complexes containing both Binap (2'2'-bis(diphenylphosphino) binaphthyl) and a Z3-pinene or Z3-allyl ligand - NMR-studies on [Pd(Z3-C10H15)(S(-)Binap)] (CF3SO3) - the crystal-structure of [Pd(Z3-C10H15)(4,4'-dimethylbipyridine)](CF3SO3). J Organomet Chem 423:415
    • (1992) J Organomet Chem , vol.423 , pp. 415
    • Ammann, C.J.1    Pregosin, P.S.2    Ruegger, H.3    Albinati, A.4    Lianza, F.5    Kunz, R.W.6
  • 35
    • 0034603094 scopus 로고    scopus 로고
    • Asymmetric allyl-metal bonding in substituted (Z3-allyl)palladium complexes: X-ray structures of cis- and trans-4-acetoxy- [Z3-(1 2 3)-cyclohexenyl]palladium chloride dimers
    • Jonasson C, Kritikos M, Backvall JE, Szabo KJ (2000) Asymmetric allyl-metal bonding in substituted (Z3-allyl)palladium complexes: X-ray structures of cis- and trans-4-acetoxy- [Z3-(1,2,3)-cyclohexenyl]palladium chloride dimers. Chem-Eur J 6:432
    • (2000) Chem-Eur J. , vol.6 , pp. 432
    • Jonasson, C.1    Kritikos, M.2    Backvall, J.E.3    Szabo, K.J.4
  • 36
    • 0000446913 scopus 로고    scopus 로고
    • First-principles investigation of enantioselective catalysis: Asymmetric allylic amination with Pd complexes bearing P,N-ligands
    • Blochl PE, Togni A (1996) First-principles investigation of enantioselective catalysis: Asymmetric allylic amination with Pd complexes bearing P,N-ligands. Organometallics 15:4125
    • (1996) Organometallics , vol.15 , pp. 4125
    • Blochl, P.E.1    Togni, A.2
  • 39
    • 0000172384 scopus 로고
    • Rate and mechanism of oxidative addition of aryl triflates to zerovalent palladium complexes - evidence for the formation of cationic (sigma-aryl)palladium complexes
    • Jutand A, Mosleh A (1995) Rate and mechanism of oxidative addition of aryl triflates to zerovalent palladium complexes - evidence for the formation of cationic (sigma-aryl)palladium complexes. Organometallics 14:1810
    • (1995) Organometallics , vol.14 , pp. 1810
    • Jutand, A.1    Mosleh, A.2
  • 40
    • 0742269474 scopus 로고    scopus 로고
    • 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
    • Roy AH, Hartwig JF (2004) 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. Organometallics 23:194
    • (2004) Organometallics , vol.23 , pp. 194
    • Roy, A.H.1    Hartwig, J.F.2
  • 41
    • 8344265265 scopus 로고    scopus 로고
    • Palladium-catalyzed electrophilic allylation reactions via bis(allyl)palladium complexes and related intermediates
    • Szabo KJ (2004) Palladium-catalyzed electrophilic allylation reactions via bis(allyl)palladium complexes and related intermediates. Chem-Eur J 10:5269
    • (2004) Chem-Eur J. , vol.10 , pp. 5269
    • Szabo, K.J.1
  • 42
    • 77957202695 scopus 로고    scopus 로고
    • Memory and dynamics in Pd-catalyzed allylic alkylation with P,N-ligands
    • Johansson C, Lloyd-Jones GC, Norrby PO (2010) Memory and dynamics in Pd-catalyzed allylic alkylation with P,N-ligands. Tetrahedron-Asymmetry 21:1585
    • (2010) Tetrahedron-Asymmetry , vol.21 , pp. 1585
    • Johansson, C.1    Lloyd-Jones, G.C.2    Norrby, P.O.3
  • 43
    • 0001220639 scopus 로고
    • Effects of phenanthroline type ligands on the dynamic processes of (Z3-allyl palladium complexes - molecular-structure of 2,9-dimethyl-1,10- phenanthroline)[( 1,2,3-Z)-3-methyl- 2-butenyl]-chloropalladium
    • Hansson S, Norrby PO, Sjogren MPT, Akermark B, Cucciolito ME, Giordano F, Vitagliano A (1993) Effects of phenanthroline type ligands on the dynamic processes of (Z3-allyl)palladium complexes - molecular-structure of (2,9-dimethyl-1,10-phenanthroline)[(1,2,3-Z)-3-methyl- 2-butenyl]- chloropalladium. Organometallics 12:4940
    • (1993) Organometallics , vol.12 , pp. 4940
    • Hansson, S.1    Norrby, P.O.2    Sjogren, M.P.T.3    Akermark, B.4    Cucciolito, M.E.5    Giordano, F.6    Vitagliano, A.7
  • 44
    • 0001127958 scopus 로고
    • 2D NOESY of palladium p-allyl complexes - reporter ligands, complex dynamics, and the X-ray structure of [Pd(Z3-C4H7Bpy)](CF3SO3) (Bpy = Bipyridine
    • Albinati A, Kunz RW, Ammann CJ, Pregosin PS (1991) 2D NOESY of palladium p-allyl complexes - reporter ligands, complex dynamics, and the X-ray structure of [Pd(Z3-C4H7) (Bpy)](CF3SO3) (Bpy = Bipyridine). Organometallics 10:1800
    • (1991) Organometallics , vol.10 , pp. 1800
    • Albinati, A.1    Kunz, R.W.2    Ammann, C.J.3    Pregosin, P.S.4
  • 45
    • 0000958213 scopus 로고
    • Reactions of pyridine-2-carbaldimines with chloro-bridged palladium(II) and platinum(II) 2-methylallyl dimers - solution behavior of the cationic complexes [M(Z3-2-MeC3H4)(Py-2-CH=NR)]+
    • Crociani B, Dibianca F, Giovenco A, Boschi T (1987) Reactions of pyridine-2-carbaldimines with chloro-bridged palladium(II) and platinum(II) 2-methylallyl dimers - solution behavior of the cationic complexes [M(Z3-2-MeC3H4)(Py-2-CH=NR)]+. Inorg Chim Acta 127:169
    • (1987) Inorg Chim Acta , vol.127 , pp. 169
    • Crociani, B.1    Dibianca, F.2    Giovenco, A.3    Boschi, T.4
  • 46
    • 0001704975 scopus 로고
    • Mechanism of apparent p-allyl rotation in (p-allyl)palladium complexes with bidentate nitrogen ligands
    • Gogoll A, Ornebro J, Grennberg H, Backvall JE (1994) Mechanism of apparent p-allyl rotation in (p-allyl)palladium complexes with bidentate nitrogen ligands. J Am Chem Soc 116:3631
    • (1994) J Am Chem Soc , vol.116 , pp. 3631
    • Gogoll, A.1    Ornebro, J.2    Grennberg, H.3    Backvall, J.E.4
  • 47
    • 0141922951 scopus 로고    scopus 로고
    • QRC: A rapid method for connecting transition structures to reactants in the computational analysis of organic reactivity
    • Goodman JM, Silva MA (2003) QRC: A rapid method for connecting transition structures to reactants in the computational analysis of organic reactivity. Tetrahedron Lett 44:8233
    • (2003) Tetrahedron Lett , vol.44 , pp. 8233
    • Goodman, J.M.1    Silva, M.A.2
  • 50
    • 27144460862 scopus 로고    scopus 로고
    • The effect of chloride ions on the mechanism of the oxidative addition of cyclic allylic carbonates to Pd-0 complexes by formation of neutral [(Z1-allyl)PdClL2] complexes
    • Cantat T, Agenet N, Jutand A, Pleixats R, Moreno-Manas M (2005) The effect of chloride ions on the mechanism of the oxidative addition of cyclic allylic carbonates to Pd-0 complexes by formation of neutral [(Z1-allyl)PdClL2] complexes. Eur J Org Chem 2005:4277
    • (2005) Eur J Org Chem , vol.2005 , pp. 4277
    • Cantat, T.1    Agenet, N.2    Jutand, A.3    Pleixats, R.4    Moreno-Manas, M.5
  • 51
    • 0000674932 scopus 로고
    • Isomerization of (p-allyl)palladium complexes via nucleophilic displacement by palladium( 0) - A common mechanism in palladium(0)-catalyzed allylic substitution
    • Granberg KL, Backvall JE (1992) Isomerization of (p-allyl)palladium complexes via nucleophilic displacement by palladium(0) - a common mechanism in palladium(0)-catalyzed allylic substitution. J Am Chem Soc 114:6858
    • (1992) J Am Chem Soc , vol.114 , pp. 6858
    • Granberg, K.L.1    Backvall, J.E.2
  • 53
    • 7944231353 scopus 로고
    • A molecular-Orbital analysis of the regioselectivity of nucleophilic-addition to Z3-allyl complexes and the conformation of the Z3-allyl ligand in L3(CO)2(Z3-C3H5)MoII complexes
    • Curtis MD, Eisenstein O (1984) A molecular-Orbital analysis of the regioselectivity of nucleophilic-addition to Z3-allyl complexes and the conformation of the Z3-allyl ligand in L3(CO)2(Z3-C3H5)MoII complexes. Organometallics 3:887
    • (1984) Organometallics , vol.3 , pp. 887
    • Curtis, M.D.1    Eisenstein, O.2
  • 54
    • 33847085179 scopus 로고
    • Cyclopropanation of ester enolates by p-allylpalladium chloride complexes
    • Hegedus LS, Darlington WH, Russell CE (1980) Cyclopropanation of ester enolates by p-allylpalladium chloride complexes. J Org Chem 45:5193
    • (1980) J Org Chem , vol.45 , pp. 5193
    • Hegedus, L.S.1    Darlington, W.H.2    Russell, C.E.3
  • 55
    • 0001525065 scopus 로고    scopus 로고
    • Central versus terminal attack in nucleophilic addition to (p-allyl)palladium complexes Ligand effects and mechanism
    • Aranyos A, Szabo KJ, Castano AM, Backvall JE (1997) Central versus terminal attack in nucleophilic addition to (p-allyl)palladium complexes. Ligand effects and mechanism. Organometallics 16:1058
    • (1997) Organometallics , vol.16 , pp. 1058
    • Aranyos, A.1    Szabo, K.J.2    Castano, A.M.3    Backvall, J.E.4
  • 56
    • 0345917657 scopus 로고    scopus 로고
    • Effects of polar gamma-substituents on the structure and stability of palladacyclobutane complexes
    • Szabo KJ (1998) Effects of polar gamma-substituents on the structure and stability of palladacyclobutane complexes. J Mol Struc-Theochem 455:205
    • (1998) J Mol Struc-Theochem , vol.455 , pp. 205
    • Szabo, K.J.1
  • 57
    • 0001459529 scopus 로고    scopus 로고
    • Regioselectivity of nucleophilic attack on [Pd(allyl)(phosphine)(imine)] complexes: A theoretical study
    • Ward TR (1996) Regioselectivity of nucleophilic attack on [Pd(allyl)(phosphine)(imine)] complexes: A theoretical study. Organometallics 15:2836
    • (1996) Organometallics , vol.15 , pp. 2836
    • Ward, T.R.1
  • 58
    • 0000899217 scopus 로고    scopus 로고
    • Steric influences on the selectivity in palladium-catalyzed allylation
    • Oslob JD, Akermark B, Helquist P, Norrby PO (1997) Steric influences on the selectivity in palladium-catalyzed allylation. Organometallics 16:3015
    • (1997) Organometallics , vol.16 , pp. 3015
    • Oslob, J.D.1    Akermark, B.2    Helquist, P.3    Norrby, P.O.4
  • 59
    • 79951972572 scopus 로고    scopus 로고
    • G- and d-lactams through palladium-catalyzed intramolecular alkylation: Enantioselective synthesis NMR investigation, and DFT rationalization
    • Bantreil X, Prestat G, Moreno A, Madec D, Fristrup P, Norrby PO, Pregosin PS, Poli G (2011) g- and d-lactams through palladium-catalyzed intramolecular alkylation: Enantioselective synthesis, NMR investigation, and DFT rationalization. Chem-Eur J 17:2885
    • (2011) Chem-Eur J. , vol.17 , pp. 2885
    • Bantreil, X.1    Prestat, G.2    Moreno, A.3    Madec, D.4    Fristrup, P.5    Norrby, P.O.6    Pregosin, P.S.7    Poli, G.8
  • 60
    • 45849141251 scopus 로고    scopus 로고
    • (N, N) vs. (N, S) chelation of palladium in asymmetric allylic substitution using bis(thiazoline) ligands: A theoretical and experimental study
    • Betz A, Yu L, Reiher M, Gaumont AC, Jaffres PA, GuleaM(2008) (N, N) vs. (N, S) chelation of palladium in asymmetric allylic substitution using bis(thiazoline) ligands: A theoretical and experimental study. J Organomet Chem 693:2499
    • (2008) J Organomet Chem , vol.693 , pp. 2499
    • Betz, A.1    Yu, L.2    Reiher, M.3    Gaumont, A.C.4    Jaffres, P.A.5    Gulea, M.6
  • 61
    • 67651233273 scopus 로고    scopus 로고
    • Structure-based rationale for selectivity in the asymmetric allylic alkylation of cycloalkenyl esters employing the Trost 'Standard Ligand' (TSL): Isolation, analysis and alkylation of the monomeric form of the cationic Z3-cyclohexenyl complex [(Z3-c-C6H9)Pd(TSL)](+
    • Butts CP, Filali E, Lloyd-Jones GC, Norrby PO, Sale DA, Schramm Y (2009) Structure-based rationale for selectivity in the asymmetric allylic alkylation of cycloalkenyl esters employing the Trost 'Standard Ligand' (TSL): Isolation, analysis and alkylation of the monomeric form of the cationic Z3-cyclohexenyl complex [(Z3-c-C6H9)Pd(TSL)](+). J Am Chem Soc 131:9945
    • (2009) J Am Chem Soc , vol.131 , pp. 9945
    • Butts, C.P.1    Filali, E.2    Lloyd-Jones, G.C.3    Norrby, P.O.4    Sale, D.A.5    Schramm, Y.6
  • 62
    • 1642419559 scopus 로고    scopus 로고
    • Effect of chelating vs. bridging coordination of chiral short-bite P-X-P (X = C, N, O) ligands in enantioselective palladium-catalysed allylic substitution reactions
    • Calabro G, Drommi D, Bruno G, Faraone F (2004) Effect of chelating vs. bridging coordination of chiral short-bite P-X-P (X = C, N, O) ligands in enantioselective palladium-catalysed allylic substitution reactions. Dalton Trans 2004:81
    • (2004) Dalton Trans , vol.2004 , pp. 81
    • Calabro, G.1    Drommi, D.2    Bruno, G.3    Faraone, F.4
  • 63
    • 75649113380 scopus 로고    scopus 로고
    • A new class of modular P N-ligand library for asymmetric Pd-catalyzed allylic substitution reactions: A study of the key Pd-p-allyl intermediates
    • Mazuela J, Paptchikhine A, Tolstoy P, Pamies O, Dieguez M, Andersson PG (2010) A new class of modular P, N-ligand library for asymmetric Pd-catalyzed allylic substitution reactions: A study of the key Pd-p-allyl intermediates. Chem-Eur J 16:620
    • (2010) Chem-Eur J. , vol.16 , pp. 620
    • Mazuela, J.1    Paptchikhine, A.2    Tolstoy, P.3    Pamies, O.4    Dieguez, M.5    Andersson, P.G.6
  • 66
    • 33750702852 scopus 로고    scopus 로고
    • DFT study on the palladium-catalyzed allylation of primary amines by allylic alcohol
    • Piechaczyk O, Thoumazet C, Jean Y, le Floch P (2006) DFT study on the palladium-catalyzed allylation of primary amines by allylic alcohol. J Am Chem Soc 128:14306
    • (2006) J Am Chem Soc , vol.128 , pp. 14306
    • Piechaczyk, O.1    Thoumazet, C.2    Jean, Y.3    Le Floch, P.4
  • 67
    • 18244393989 scopus 로고    scopus 로고
    • Surprisingly mild "enolate-counterion-free" Pd(0)-catalyzed intramolecular allylic alkylations
    • Madec D, Prestat G, Martini E, Fristrup P, Poli G, Norrby PO (2005) Surprisingly mild "enolate-counterion-free" Pd(0)-catalyzed intramolecular allylic alkylations. Org Lett 7:995
    • (2005) Org Lett , vol.7 , pp. 995
    • Madec, D.1    Prestat, G.2    Martini, E.3    Fristrup, P.4    Poli, G.5    Norrby, P.O.6
  • 68
    • 0000424315 scopus 로고    scopus 로고
    • Nature of the interactions between the b-silyl substituent and allyl moiety in (Z3-allyl)palladium complexes. A combined experimental and theoretical study
    • Macsari I, Szabo KJ (1999) Nature of the interactions between the b-silyl substituent and allyl moiety in (Z3-allyl)palladium complexes. a combined experimental and theoretical study. Organometallics 18:701
    • (1999) Organometallics , vol.18 , pp. 701
    • Macsari, I.1    Szabo, K.J.2
  • 69
    • 0029792262 scopus 로고    scopus 로고
    • Effects of b-substituents and ancillary ligands on the structure and stability of (Z3-allyl)palladium complexes. implications for the regioselectivity in nucleophilic addition reactions
    • Szabo KJ (1996) Effects of b-substituents and ancillary ligands on the structure and stability of (Z3-allyl)palladium complexes. implications for the regioselectivity in nucleophilic addition reactions. J Am Chem Soc 118:7818
    • (1996) J Am Chem Soc , vol.118 , pp. 7818
    • Szabo, K.J.1
  • 70
    • 0030898249 scopus 로고    scopus 로고
    • Nature of the interactions between polar b-substituents and palladium in Z3-allylpalladium complexes - A combined experimental and theoretical study
    • Szabo KJ (1997) Nature of the interactions between polar b-substituents and palladium in Z3-allylpalladium complexes - a combined experimental and theoretical study. Chem-Eur J 3:592
    • (1997) Chem-Eur J. , vol.3 , pp. 592
    • Szabo, K.J.1
  • 71
    • 57249115727 scopus 로고    scopus 로고
    • Nature of the interaction between b-substituents and the allyl moiety in (Z3-allyl)palladium complexes
    • Szabo KJ (2001) Nature of the interaction between b-substituents and the allyl moiety in (Z3-allyl)palladium complexes. Chem Soc Rev 30:136
    • (2001) Chem Soc Rev , vol.30 , pp. 136
    • Szabo, K.J.1
  • 72
    • 0000669372 scopus 로고    scopus 로고
    • Stereoelectronic control on the kinetic stability of b-acetoxy- substituted (Z3-allyl)palladium com plexes in a mild acidic medium
    • Szabo KJ, Hupe E, Larsson ALE (1997) Stereoelectronic control on the kinetic stability of b-acetoxy-substituted (Z3-allyl)palladium com plexes in a mild acidic medium. Organometallics 16:3779
    • (1997) Organometallics , vol.16 , pp. 3779
    • Szabo, K.J.1    Hupe, E.2    Larsson, A.L.E.3
  • 73
    • 33847085445 scopus 로고
    • A palladium-catalyzed reaction of a p-allyl ligand with a nucleophile - an MO study about a feature of the reaction and a ligand effect on the reactivity
    • Sakaki S, Nishikawa M, Ohyoshi A (1980) A palladium-catalyzed reaction of a p-allyl ligand with a nucleophile - an MO study about a feature of the reaction and a ligand effect on the reactivity. J Am Chem Soc 102:4062
    • (1980) J Am Chem Soc , vol.102 , pp. 4062
    • Sakaki, S.1    Nishikawa, M.2    Ohyoshi, A.3
  • 74
    • 84961980421 scopus 로고    scopus 로고
    • Electronic differentiations in palladium alkene complexes: Trans-phosphine preference of allylic leaving groups
    • Goldfuss B, Kazmaier U (2000) Electronic differentiations in palladium alkene complexes: Trans-phosphine preference of allylic leaving groups. Tetrahedron 56:6493
    • (2000) Tetrahedron , vol.56 , pp. 6493
    • Goldfuss, B.1    Kazmaier, U.2
  • 75
    • 37349036875 scopus 로고    scopus 로고
    • Memory effects in palladium-catalyzed allylic Alkylations of 2-cyclohexen-1-yl acetate
    • Svensen N, Fristrup P, Tanner D, Norrby PO (2007) Memory effects in palladium-catalyzed allylic Alkylations of 2-cyclohexen-1-yl acetate. Adv Synth Catal 349:2631
    • (2007) Adv Synth Catal , vol.349 , pp. 2631
    • Svensen, N.1    Fristrup, P.2    Tanner, D.3    Norrby, P.O.4
  • 76
    • 0028022655 scopus 로고
    • On the nature of the asymmetric induction in a palladium-catalyzed allylic alkylation
    • Trost BM, Breit B, Organ MG (1994) On the nature of the asymmetric induction in a palladium-catalyzed allylic alkylation. Tetrahedron Lett 35:5817
    • (1994) Tetrahedron Lett , vol.35 , pp. 5817
    • Trost, B.M.1    Breit, B.2    Organ, M.G.3
  • 78
    • 0000874560 scopus 로고    scopus 로고
    • Ab initio MO study of the geometry, Z3 , Z1 conversion, and reductive elimination of a palladium(II) Z3-allyl hydride complex and its platinum(II) analogue
    • Sakaki S, Satoh H, Shono H, Ujino Y (1996) Ab initio MO study of the geometry, Z3 , Z1 conversion, and reductive elimination of a palladium(II) Z3-allyl hydride complex and its platinum(II) analogue. Organometallics 15:1713
    • (1996) Organometallics , vol.15 , pp. 1713
    • Sakaki, S.1    Satoh, H.2    Shono, H.3    Ujino, Y.4
  • 79
    • 0000976398 scopus 로고    scopus 로고
    • Theoretical study of the structure, bonding nature, and reductive elimination reaction of Pd(XH3)( Z3-C3H5) (PH3) (X = C, Si, Ge, Sn) Hypervalent behavior of group 14 elements
    • Biswas B, Sugimoto M, Sakaki S (1999) Theoretical study of the structure, bonding nature, and reductive elimination reaction of Pd(XH3)( Z3-C3H5) (PH3) (X = C, Si, Ge, Sn). Hypervalent behavior of group 14 elements. Organometallics 18:4015
    • (1999) Organometallics , vol.18 , pp. 4015
    • Biswas, B.1    Sugimoto, M.2    Sakaki, S.3
  • 80
    • 0037119305 scopus 로고    scopus 로고
    • Intramolecular coupling of allyl carboxylates with allyl stannanes and allyl silanes: A new type of reductive elimination reaction?
    • Mendez M, Cuerva JM, Gomez-Bengoa E, Cardenas DJ, EchavarrenAM(2002) Intramolecular coupling of allyl carboxylates with allyl stannanes and allyl silanes: A new type of reductive elimination reaction? Chem-Eur J 8:3620
    • (2002) Chem-Eur J. , vol.8 , pp. 3620
    • Mendez, M.1    Cuerva, J.M.2    Gomez-Bengoa, E.3    Cardenas, D.J.4    Echavarren, A.M.5
  • 81
    • 37049114298 scopus 로고
    • Palladium-catalysed hydrosilation of olefins and polyenes
    • Hara M, Ohno K, Tsuji J (1971) Palladium-catalysed hydrosilation of olefins and polyenes. J Chem Soc D - Chem Comm 1971:247
    • (1971) J Chem Soc D - Chem Comm , vol.1971 , pp. 247
    • Hara, M.1    Ohno, K.2    Tsuji, J.3
  • 82
    • 37049089453 scopus 로고
    • Palladium-catalyzed and platinum-catalyzed addition of aldehydes with allylstannanes
    • Nakamura H, Asao N, Yamamoto Y (1995) Palladium-catalyzed and platinum-catalyzed addition of aldehydes with allylstannanes. J Chem Soc Chem Commun 1995:1273
    • (1995) J Chem Soc Chem Commun , vol.1995 , pp. 1273
    • Nakamura, H.1    Asao, N.2    Yamamoto, Y.3
  • 83
    • 0035831228 scopus 로고    scopus 로고
    • Control of the regioselectivity in catalytic transformations involving amphiphilic bis-allylpalladium intermediates: Mechanism and synthetic applications
    • Solin N, Narayan S, Szabo KJ (2001) Control of the regioselectivity in catalytic transformations involving amphiphilic bis-allylpalladium intermediates: Mechanism and synthetic applications. J Org Chem 66:1686
    • (2001) J Org Chem , vol.66 , pp. 1686
    • Solin, N.1    Narayan, S.2    Szabo, K.J.3
  • 84
    • 58149161551 scopus 로고    scopus 로고
    • On the nature of the intermediates and the role of chloride ions in Pd-catalyzed allylic alkylations: Added insight from density functional theory
    • Fristrup P, Ahlquist M, Tanner D, Norrby PO (2008) On the nature of the intermediates and the role of chloride ions in Pd-catalyzed allylic alkylations: Added insight from density functional theory. J Phys Chem A 112:12862
    • (2008) J Phys Chem A. , vol.112 , pp. 12862
    • Fristrup, P.1    Ahlquist, M.2    Tanner, D.3    Norrby, P.O.4
  • 85
    • 33746347045 scopus 로고    scopus 로고
    • Cationic (Z1-allyl)-palladium complexes as feasible intermediates in catalyzed reactions
    • Garcia-Iglesias M, Bunuel E, Cardenas DJ (2006) Cationic (Z1-allyl)-palladium complexes as feasible intermediates in catalyzed reactions. Organometallics 25:3611
    • (2006) Organometallics , vol.25 , pp. 3611
    • Garcia-Iglesias, M.1    Bunuel, E.2    Cardenas, D.J.3
  • 86
    • 34250816839 scopus 로고    scopus 로고
    • Synthesis and catalytic application of chiral 1,1'-bi-2-naphthol- and biphenanthrol-based pincer complexes: Selective allylation of sulfonimines with allyl stannane and allyl trifluoroborate
    • Aydin J, Kumar KS, Sayah MJ, Wallner OA, Szabo KJ (2007) Synthesis and catalytic application of chiral 1,1'-bi-2-naphthol- and biphenanthrol-based pincer complexes: Selective allylation of sulfonimines with allyl stannane and allyl trifluoroborate. J Org Chem 72:4689
    • (2007) J Org Chem , vol.72 , pp. 4689
    • Aydin, J.1    Kumar, K.S.2    Sayah, M.J.3    Wallner, O.A.4    Szabo, K.J.5
  • 87
    • 0001430247 scopus 로고    scopus 로고
    • Palladium-catalyzed tandem bis-allylation of isocyanates
    • Solin N, Narayan S, Szabo KJ (2001) Palladium-catalyzed tandem bis-allylation of isocyanates. Org Lett 3:909
    • (2001) Org Lett , vol.3 , pp. 909
    • Solin, N.1    Narayan, S.2    Szabo, K.J.3
  • 88
    • 3042774302 scopus 로고    scopus 로고
    • Pincer complex-catalyzed allylation of aldehyde and imine substrates via nucleophilic Z1-allyl palladium intermediates
    • Solin N, Kjellgren J, Szabo KJ (2004) Pincer complex-catalyzed allylation of aldehyde and imine substrates via nucleophilic Z1-allyl palladium intermediates. J Am Chem Soc 126:7026
    • (2004) J Am Chem Soc , vol.126 , pp. 7026
    • Solin, N.1    Kjellgren, J.2    Szabo, K.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.