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Theoretical Evaluation of Phosphine Effects in Cross-Coupling Reactions

  • Max García-Melchor
  • Gregori Ujaque
  • Feliu Maseras
  • Agustí Lledós
Chapter
Part of the Catalysis by Metal Complexes book series (CMCO, volume 37)

Abstract

Cross-coupling reactions are one of the most useful reactions in organic synthesis. Among all the transition metal complexes developed as catalysts for this reaction those based on Pd are by far the most utilized ones. The most common stoichiometry of this family of catalyst is PdL2 with L = phosphine ligands. The effects of the phosphine ligands on the reaction mechanism evaluated by means of theoretical calculations are reviewed in these lines. How the nature of the phosphine ligand affects each of the elementary processes involved in a cross-coupling reaction, namely oxidative addition, transmetalation and reductive elimination will be exposed separately. The transmetalation process has its own particular mechanistic details depending on the cross-coupling reaction; those for the Suzuki–Miyaura and Stille reactions will be described here. The dichotomy between the monophosphine and bisphosphine reaction pathways will be also discussed.

Keywords

Oxidative Addition Phosphine Ligand Reductive Elimination High Energy Barrier Aryl Chloride 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Notes

Acknowledgments

We thank the Ph.D. students and postdocs who have contributed to developing this research topic in our groups. Fruitful collaborations with experimental groups (Pablo Espinet, Gregorio Asensio, Rosana Alvarez and Angel Rodríguez de Lera) are also acknowledged. The Spanish MICINN is gratefully acknowledged for funding this research through projects CTQ2008-06866-C02-01, CTQ2008-06866-C02-02 and Consolider-Ingenio 2010 (CSD2007-00006 and CSD2006-0003).

References

  1. 1.
    Cornils B, Herrmann WA (2002) Applied homogeneous catalysis with organometallic compounds. Wiley-VCH, WeinheimGoogle Scholar
  2. 2.
    Hagen J (2006) Industrial catalysis: a practical approach, 2nd edn. Wiley-VCH, WeinheimGoogle Scholar
  3. 3.
    Miura M (2004) Rational ligand design in constructing efficient catalyst systems for Suzuki–Miyaura coupling. Angew Chem Int Ed 43:2201–2203Google Scholar
  4. 4.
    Chen W, Li R, Han B, Li B-J, Chen Y-C, Wu Y, Ding L-S, Yang D (2006) The design and synthesis of bis(thiourea) ligands and their application in Pd-catalyzed Heck and Suzuki reactions under aerobic conditions. Eur J Org Chem 1177–1184Google Scholar
  5. 5.
    Tolman CA (1977) Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis. Chem Rev 77:313–348Google Scholar
  6. 6.
    Brown TL, Lee KJ (1993) Ligand steric properties. Coord Chem Rev 128:89–116Google Scholar
  7. 7.
    Dias PB, de Piedade MEM, Martinho Simões JA (1994) Bonding and energetics of phosphorus (III) ligands in transition metal complexes. Coord Chem Rev 135(136):737–807Google Scholar
  8. 8.
    Bunten KA, Chen L, Fernandez AL, Poë AJ (2002) Cone angles: Tolman’s and Plato’s. Coord Chem Rev 233(234):41–51Google Scholar
  9. 9.
    Kühl O (2005) Predicting the net donating ability of phosphines- do we need sophisticated theoretical methods? Coord Chem Rev 249:693–704Google Scholar
  10. 10.
    Kamer PCJ, van Leeuwen PWNM, Reek JNH (2001) Wide bite angle diphosphines: Xantphos ligands in transition metal complexes and catalysis. Acc Chem Res 34:895–904Google Scholar
  11. 11.
    Wang Y, Wang J, Su J, Huang F, Jiao L, Liang Y, Yang D, Zhang S, Wender PA, Yu Z-X (2007) A computational designed Rh(I)-catalyzed two-component [5 + 2 + 1] cycloaddition of ene-vinylcyclopropanes and CO for the synthesis of cyclooctenones. J Am Chem Soc 129:10060–10061Google Scholar
  12. 12.
    Houk KN, Cheong PH-Y (2008) Computational prediction of small-molecule catalysts. Nature 455(7211):309–313Google Scholar
  13. 13.
    Ananikov VP, Orlov NV, Kabeshov MA, Beletskaya IP, Starikova ZA (2008) Stereodefined synthesis of a new type of 1,3-dienes by ligand-controlled carbon-carbon and carbon-heteroatom bond formation in nickel-catalyzed reaction of diaryldichalcogenides with alkynes. Organometallics 27:4056–4061Google Scholar
  14. 14.
    Abe Y, Kuramoto K, Ehara M, Nakatsuji H, Suginome M, Murakami M, Ito Y (2008) A mechanism for the palladium-catalyzed regioselective silaboration of allene: a theoretical study. Organometallics 27:1736–1742Google Scholar
  15. 15.
    Maseras F, Morokuma K (1995) IMOMM: A new integrated ab initio + molecular mechanics geometry optimization scheme of equilibrium structures and transition states. J Comput Chem 16:1055–1179Google Scholar
  16. 16.
    Ujaque G, Maseras F (2004) Applications of hybrid DFT/molecular mechanics to homogeneous catalysis. Struct Bond 112:117–149Google Scholar
  17. 17.
    Bo C, Maseras F (2008) QM/MM methods in inorganic chemistry. Dalton Trans 2911–2919Google Scholar
  18. 18.
    Carbo JJ, Maseras F, Bo C, van Leeuwen WNM (2001) Unraveling the origin of regioselectivity in rhodium diphosphine catalyze hydroformylation. A DFT QM/MM study. J Am Chem Soc 123:7630–7637Google Scholar
  19. 19.
    Garcia-Cuadrado D, de Mendoza P, Braga AAC, Maseras F, Echavarren AM (2007) Proton-abstraction mechanism in the palladium-catalyzed intramolecular arylation: substituents effects. J Am Chem Soc 129:6880–6886Google Scholar
  20. 20.
    Liu S, Saidi O, Berry N, Ruan J, Pettman A, Thomson N, Xiao J (2009) Electron-deficient phosphines accelerate the Heck reaction of electron-rich olefins in ionic liquids. Lett Org Chem 6:60–64Google Scholar
  21. 21.
    Moncho S, Ujaque G, Lledos A, Espinet P (2008) When are tricoordinated PdII species accessible? Stability trends and mechanistic consequences. Chem Eur J 14:8986–8994Google Scholar
  22. 22.
    de Meijere A, Diederich F (2004) Metal-catalyzed cross-coupling reactions. Wiley-VCH, WeinheimGoogle Scholar
  23. 23.
    Cross-Coupling reactions: A practical guide (2001) No 219. In: Miyaura N (ed) Topics in current chemistry. Springer, BerlinGoogle Scholar
  24. 24.
    Buchwald SL (ed) (2008) Cross-coupling. Acc Chem Res 41(special issue):1439–1564Google Scholar
  25. 25.
    Tamao K, Hiyama T, Negishi E (eds) (2002) 30 years of cross-coupling reaction. J Organomet Chem 653(special issue):1–303Google Scholar
  26. 26.
    Phapale VB, Cardenas DJ (2009) Nickel-catalyzed Negishi cross-coupling reactions: scope and mechanisms. Chem Soc Rev 38:1598–1607Google Scholar
  27. 27.
    Nicolaou KC, Bulger PG, Sarlah D (2005) Palladium-catalyzed cross-coupling reactions in total synthesis. Angew Chem Int Ed 44:4442–4489Google Scholar
  28. 28.
    Xue L, Lin Z (2010) Theoretical aspects of palladium-catalyzed carbon-carbon cross-coupling reactions. Chem Soc Rev 39:1692Google Scholar
  29. 29.
    Kosugi M, Sasazawa K, Shimizu Y, Migita T (1977) Reactions of allyltin compounds. 3. Allylation of aromatic halides with allyltributyltin in presence of tetrakis(triphenylphosphine)palladium(0). Chem Lett 3:301–302Google Scholar
  30. 30.
    Stille JK (1986) The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles. Angew Chem Int Ed 25:508–524Google Scholar
  31. 31.
    Miyaura N, Yamada K, Suzuki A (1979) New stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Lett 36:3437–3440Google Scholar
  32. 32.
    Miyaura N, Suzuki A (1995) Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 95:2457–2483Google Scholar
  33. 33.
    Negishi E, King AO, Okukado N (1977) Selective carbon-carbon bond formation via transition-metal catalysis. 3. Highly selective synthesis of unsymmetrical biaryls and diarylmethanes by nickel-catalyzed or palladium-catalyzed reaction of aryl derivatives and benzylzinc derivatives with aryl halides. J Org Chem 42:1821–1823Google Scholar
  34. 34.
    Fuentes B, García-Melchor M, Lledos A, Maseras F, Casares JA, Ujaque G, Espinet P (2010) Palladium round trip in the Negishi coupling of trans-[PdMeCl(PMePh2)2] with ZnMeCl: An experimental and DFT study of the transmetalation step. Chem Eur J 16:8596–8599Google Scholar
  35. 35.
    Braga AAC, Ujaque G, Maseras F (2008) Mechanism of palladium-catalyzed cross-coupling reactions. In: Morokuma K, Musaev DG (eds) Computational modeling for homogeneous and enzymatic catalysis. Wiley-VCH, WeinheimGoogle Scholar
  36. 36.
    Amatore C, Jutand A (2000) Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions. Acc Chem Res 33:314–321Google Scholar
  37. 37.
    Galardon E, Ramdeehul S, Brown JM, Cowley A, Hii KK, Jutand A (2002) Profund steric control of reactivity in aryl halide addition to bisphosphane palladium(0) complexes. Angew Chem Int Ed 41:1760–1763Google Scholar
  38. 38.
    Hartwig JF (2007) Electronic effects on reductive elimination to form carbon-carbon and carbon-heteroatom bonds from palladium(II) complexes. Inorg Chem 46:1936–1947Google Scholar
  39. 39.
    Yandulov DV, Tran NT (2007) Aryl-Fluoride reductive elimination from Pd(II): Feasibility assessment from theory and experiment. J Am Chem Soc 129:1342–1358Google Scholar
  40. 40.
    Senn HM, Ziegler T (2004) Oxidative addition of aryl halides to palladium(0) complexes: A density-functional study including solvation. Organometallics 23:2980–2988Google Scholar
  41. 41.
    Gossen LJ, Koley D, Hermann HL, Thiel W (2005) Mechanistic pathways for oxidative addition of aryl halides to palladium(0) complexes: A DFT study. Organometallics 24:2398–2410Google Scholar
  42. 42.
    Lam KC, Marder TB, Lin Z (2007) DFT studies on the effect of the nature of the aryl halide Y-C6H4-X on the mechanism of its oxidative addition to Pd0L versus Pd0L2. Organometallics 26:758–760Google Scholar
  43. 43.
    Casado AL, Espinet P (1998) Mechanism of the Stille reaction. 1. The transmetalation step. Coupling of R1I and R2SnBu3 catalyzed by trans-[PdR1IL2] (R1 = C6Cl2F3; R2 = vinyl, 4-methoxyphenyl; L = AsPh3). J Am Chem Soc 120:8978–8985Google Scholar
  44. 44.
    Sicre C, Braga AAC, Maseras F, Cid MM (2008) Mechanistic insights into the transmetalation step of a Suzuki-Miyaura reaction of 2(4)-bromopyridines: Characterization of an intermediate. Tetrahedron 64:7437–7443Google Scholar
  45. 45.
    Liu Q, Lan Y, Liu J, Li G, Wu Y-D, Lei A (2009) Revealing a second transmetalation step in the Negishi coupling and its competition with reductive elimination: Improvement in the interpretation of the mechanism of biaryl synthesis. J Am Chem Soc 131:10201–10210Google Scholar
  46. 46.
    Littke AF, Fu GC (2002) Palladium-catalyzed coupling reactions of aryl chlorides. Angew Chem Int Ed 41:4176–4211Google Scholar
  47. 47.
    Wolfe JP, Singer RA, Yang BH, Buchwald SL (1999) Highly active palladium catalysts for Suzuki coupling reactions. J Am Chem Soc 121:9550–9561Google Scholar
  48. 48.
    Zapf A, Ehrentraut A, Beller M (2000) A new highly efficient catalyst system for the coupling of nonactivated and deactivated aryl chlorides with arylboronic acids. Angew Chem Int Ed 39:4153–4155Google Scholar
  49. 49.
    Fleckenstein CA, Plenio H (2010) Sterically demanding trialkylphosphines for palladium-catalyzed cross-coupling reactions- alternatives to Pt-Bu3. Chem Soc Rev 39:694–711Google Scholar
  50. 50.
    Kantchev EAB, O’Brien CJ, Organ MG (2007) Palladium complexes of N-Heterocyclic carbenes as catalysts for cross-coupling reactions. A synthetic chemist’s perspective. Angew Chem Int Ed 46:2768–2813Google Scholar
  51. 51.
    Marion N, Nolan SP (2008) Well-defined N-Heterocyclic carbenes-palladium(II) precatalysts for cross-coupling reactions. Acc Chem Res 41:1440–1449Google Scholar
  52. 52.
    Ahlquist M, Fristrup P, Tanner D, Norrby P-O (2006) Theoretical evidence for low-ligated palladium(0): [Pd–L] as the active species in oxidative addition. Organometallics 25:2066–2073Google Scholar
  53. 53.
    Li Z, Fu Y, Guo Q-X, Liu L (2008) Theoretical study on monoligated Pd-catalyzed cross-coupling reactions of aryl chlorides and bromides. Organometallics 27:4043–4049Google Scholar
  54. 54.
    Ariafard A, Yates BF (2009) Subtle balance of ligand steric effects in Stille transmetalation. J Am Chem Soc 131:13981–13991Google Scholar
  55. 55.
    Barrios-Landeros F, Carrow BP, Hartwig JF (2009) Effect of ligand steric properties and halide identity on the mechanism for oxidative addition of haloarenes to trialkylphosphine Pd(0) complexes. J Am Chem Soc 131:8141–8154Google Scholar
  56. 56.
    Ahlquist M, Norrby P-O (2007) Oxidative addition of aryl chlorides to monoligated palladium(0): A DFT-SCRF study. Organometallics 26:550–553Google Scholar
  57. 57.
    Jover J, Fey N, Purdie M, Lloyd-Jones GC, Harvey JN (2010) A computational study of phosphine ligand effects in Suzuki-Miyaura coupling. J Mol Catal A 324:39–47Google Scholar
  58. 58.
    Fey N, Tsipis AC, Harris SE, Harvey JN, Orpen AG, Mansson RA (2006) Development of a ligand knowledge base, Part 1: Computational descriptors for phosphorus donor ligands. Chem Eur J 12:291–302Google Scholar
  59. 59.
    Fey N, Orpen GA, Harvey JN (2009) Building ligand knowledge bases for organometallic chemistry: Computational description of phosphorus(III)-donor ligands and the metal-phosphorus bond. Coord Chem Rev 253:704–722Google Scholar
  60. 60.
    Fey N (2010) The contribution of computational studies to organometallic catalysis: descriptors, mechanisms and models. Dalton Trans 39:296–310Google Scholar
  61. 61.
    Corbet J-P, Mignani G (2006) Selected patented cross-coupling reaction technologies. Chem Rev 106:2651–2710Google Scholar
  62. 62.
    Stille JK, Lau KS (1977) Mechanisms of oxidative addition of organic halides to group-8 transition metal complexes. Acc Chem Res 10:434–442Google Scholar
  63. 63.
    Feliz M, Freixa Z, van Leeuwen PWNM, Bo C (2005) Revisiting the methyl iodide oxidative addition to rhodium complexes: A DFT study of the activation parameters. Organometallics 24:5718–5723Google Scholar
  64. 64.
    Diefenbach A, de Jong GT, Bickelhaupt FM (2005) Activation of H–H, C–H, C–C and C–Cl bonds by Pd and PdCl. Understanding anion assistance in C–X bond activation. J Chem Theory Comput 1:286–298Google Scholar
  65. 65.
    Rodriguez N, Ramirez de Arellano C, Asensio G, Medio-Simon M (2007) Palladium-catalyzed Suzuki-Miyaura reaction involving a secondary sp3 carbon: Studies of stereochemistry and scope of the reaction. Chem Eur J 13:4223–4229Google Scholar
  66. 66.
    Gourlaouen C, Ujaque G, Lledos A, Medio-Simon M, Asensio G, Maseras F (2009) Why is the Suzuki–Miyaura cross-coupling of sp3 carbons in α-Bromo sulfoxide systems fast and stereoselective? A DFT study on the mechanism. J Org Chem 74:4049–4054Google Scholar
  67. 67.
    Miyaura N (2002) Cross-coupling reaction of organoboron compounds via base-assisted transmetalation to palladium(II) complexes. J Organomet Chem 653:54–57Google Scholar
  68. 68.
    Smith GB, Dezeny GC, Hughes DL, King AO, Verhoeven TR (1994) Mechanistic studies of the Suzuki cross-coupling reaction. J Org Chem 59:8151–8156Google Scholar
  69. 69.
    Matos K, Soderquist JA (1998) Alkylboranes in the Suzuki–Miyaura coupling: stereochemical and mechanistic studies. J Org Chem 63:461–470Google Scholar
  70. 70.
    Braga AAC, Morgon NH, Ujaque G, Maseras F (2005) Computational characterization of the role of the base in the Suzuki–Miyaura cross-coupling reaction. J Am Chem Soc 127:9298–9307Google Scholar
  71. 71.
    Braga AAC, Ujaque G, Maseras F (2006) A DFT study of the full catalytic cycle of the Suzuki-Miyaura cross-coupling on a model system. Organometallics 25:3647–3658Google Scholar
  72. 72.
    Braga AAC, Morgon NH, Ujaque G, Lledos A, Maseras F (2006) Computational study of the transmetalation process in the Suzuki-Miyaura cross-coupling of aryls. J Organomet Chem 691:4459–4466Google Scholar
  73. 73.
    Sumimoto M, Iwane N, Takahama T, Sakaki S (2004) Theoretical study of trans-metalation process in palladium-catalyzed borylation of iodobenzene with diboron. J Am Chem Soc 126:10457–10471Google Scholar
  74. 74.
    Gooβen LJ, Koley D, Hermann HL, Thiel W (2005) The palladium-catalyzed cross-coupling reaction of carboxylic anhydrides with arylboronic acids: a DFT study. J Am Chem Soc 127:11102–11114Google Scholar
  75. 75.
    Gooβen LJ, Koley D, Hermann HL, Thiel W (2006) Palladium monophosphine intermediates in catalytic cross-coupling reactions: a DFT study. Organometallics 25:54–67Google Scholar
  76. 76.
    Martin R, Buchwald SL (2008) Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands. Acc Chem Res 41:1461–1473 (references therein)Google Scholar
  77. 77.
    Barder TE, Walker SD, Martinelli JR, Buchwald SL (2005) Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of the ligand structure. J Am Chem Soc 127:4685–4696Google Scholar
  78. 78.
    Christmann U, Vilar R (2005) Monoligated palladium species as catalyst in cross-coupling reactions. Angew Chem Int Ed 44:366–374Google Scholar
  79. 79.
    Joshaghani M, Faramarzi E, Rafiee E, Daryanavard M, Xiao J, Baillie C (2006) Efficient Suzuki cross-coupling reactions using bulky phosphines. J Mol Catal A 259:35–40Google Scholar
  80. 80.
    Huang Y-L, Weng C-M, Hong F-E (2008) Density functional studies on palladium-catalyzed Suzuki-Miyaura cross-coupling reactions assisted by N- or P-chelating ligands. Chem Eur J 14:4426–4434Google Scholar
  81. 81.
    Chang C-P, Weng C-M, Hong F-E (2010) Preparation of cobalt sandwich diphosphine ligand [(η5–C5H4 iPr)Co(η4–C4(PPh2)2Ph2)] and its chelated palladium complex: application of diphosphine ligand in the preparation of mono-substituted ferrocenylarenes. Inorg Chim Acta 363:412–417Google Scholar
  82. 82.
    Espinet P, Echavarren AM (2004) The mechanisms of the Stille reaction. Angew Chem Int Ed 43:4704–4734Google Scholar
  83. 83.
    Ye J, Bhatt RK, Falck JR (1994) Stereospecific palladium/copper cocatalyzed cross-coupling of α-alkoxy- and α-aminostannanes with acyl chlorides. J Am Chem Soc 116:1–5Google Scholar
  84. 84.
    Labadie JW, Stille JK (1983) Mechanisms of the palladium-catalyzed couplings of acid chlorides with organotin reagents. J Am Chem Soc 105:6129–6137Google Scholar
  85. 85.
    Casares JA, Espinet P, Salas G (2002) 14-electron T-shape [PdRXL] complexes: evidence or illusion? Mechanistic consequences for the Stille reaction and related processes. Chem Eur J 8:4843–4853Google Scholar
  86. 86.
    Napolitano E, Farina V, Persico M (2003) The Stille reaction: a density functional analysis of the transmetalation and the importance of coordination expansion at Tin. Organometallics 22:4030–4037Google Scholar
  87. 87.
    Farina V, Krishnan B (1991) Large rate accelerations in the Stille reaction with tri-2-furylphosphine and triphenylarsine as palladium ligands: mechanistic and synthetic implications. J Am Chem Soc 113:9585–9595Google Scholar
  88. 88.
    Amatore C, Bahsoun AA, Jutand A, Meyer G, Ntepe AN, Ricard L (2003) Mechanism of the Stille reaction catalyzed by palladium ligated to arsine ligand: PhPdI(AsPh3)(DMF) is the species reacting with vinylstannane in DMF. J Am Chem Soc 125:4212–4222Google Scholar
  89. 89.
    Alvarez R, Faza ON, Lopez CS, de Lera AR (2006) Computational characterization of a complete palladium-catalyzed cross-coupling process: The associative transmetalation in the Stille reaction. Org Lett 8:35–38Google Scholar
  90. 90.
    Nova A, Ujaque G, Maseras F, Lledos A, Espinet P (2006) A critical analysis of the cyclic and open alternatives of the transmetalation step in the Stille cross-coupling reaction. J Am Chem Soc 128:14571–14578Google Scholar
  91. 91.
    Ariafard A, Lin Z, Fairlamb IJS (2006) Effect of the leaving ligand X on transmetalation of organostannanes (vinylSnR3) with LnPd(Ar)(X) in Stille cross-coupling reactions. A density functional theory study. Organometallics 25:5788–5794Google Scholar
  92. 92.
    Alvarez R, Perez M, Faza ON, de Lera AR (2008) Associative transmetalation in the Stille cross-coupling reaction to form dienes: Theoretical insights into the open pathway. Organometallics 27:3378–3389Google Scholar
  93. 93.
    Littke AF, Schwarz L, Fu GC (2002) Pd/P(t-Bu)3: a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides. J Am Chem Soc 124:6343–6348Google Scholar
  94. 94.
    Fazaeli R, Ariafard A, Jamshidi S, Tabatabaie ES, Pishro KA (2007) Theoretical studies of the oxidative addition of PhBr to Pd(PX3)2 and Pd(X2PCH2CH2PX2) (X = Me, H, Cl). J Organomet Chem 692:3984–3993Google Scholar
  95. 95.
    Perez-Temprano MH, Nova A, Casares JA, Espinet P (2008) Observation of a hidden intermediate in the Stille reaction. Study of the reversal of the transmetalation step. J Am Chem Soc 130:10518–10520Google Scholar
  96. 96.
    Tatsumi K, Hoffmann R, Yamamoto A, Stille JK (1981) Reductive elimination of d8-organotransition metal complexes. Bull Chem Soc Jpn 54:1857–1867Google Scholar
  97. 97.
    Low JJ, Goddard WA (1986) Theoretical studies of oxidative addition and reductive elimination. 2. Reductive coupling of H–H, H–C, and C–C bonds from palladium and platinum complexes. Organometallics 5:609–622Google Scholar
  98. 98.
    Low JJ, Goddard WA (1986) Theoretical studies of oxidative addition and reductive elimination. 3. C–H and C–C reductive coupling from palladium and platinum bis(phosphine) complexes. J Am Chem Soc 108:6115–6128Google Scholar
  99. 99.
    Ananikov VP, Musaev DG, Morokuma K (2002) Vinyl-vinyl coupling on late transition metals through C–C reductive elimination mechanism. A computational study. J Am Chem Soc 124:2839–2852Google Scholar
  100. 100.
    Ananikov VP, Musaev DG, Morokuma K (2005) Theoretical insight into the C–C coupling reactions of the vinyl, phenyl, ethynyl, and methyl complexes of palladium and platinum. Organometallics 24:715–723Google Scholar
  101. 101.
    Choueiry D, Negishi E-I (2002) Pd(0) and Pd(II) complexes containing phosphorus and other group 15 atom ligands. In: Negishi E (ed) Handbook of organopalladium chemistry for organic synthesis. Wiley, New YorkGoogle Scholar
  102. 102.
    Ozawa F, Ito T, Nakamura Y, Yamamoto A (1981) Mechanisms of thermal decomposition of trans- and cis-Dialkylbis(tertiary phosphine)palladium(II). Reductive elimination and trans to cis isomerization. Bull Chem Soc Jpn 54:1868–1880Google Scholar
  103. 103.
    Ozawa F, Kurihara K, Yamamoto T, Yamamoto A (1985) Alteration of reaction course in thermolysis of cis-diethylbis(tertiary phosphine)palladium(II) from reductive elimination to β-elimination process induced by addition of tertiary phosphine ligand. Bull Chem Soc Jpn 58:399–400Google Scholar
  104. 104.
    Brown JM, Cooley NA (1988) Carbon-carbon bond formation through organometallic elimination reactions. Chem Rev 88:1031–1046Google Scholar
  105. 105.
    Macgregor SA, Neave GW, Smith C (2003) Theoretical studies on C-heteroatom bond formation via reductive elimination from group 10 M(PH3)2(CH3)(X) species (X = CH3, NH2, OH, SH) and the determination of metal-X bond strengths using density functional theory. Faraday Discuss 124:111–127Google Scholar
  106. 106.
    Negishi E, Takahashi T, Akiyoshi K (1987) Palladium-catalyzed -or promoted reductive carbon–carbon coupling. Effects of phosphines and carbon ligands. J Organomet Chem 334:181–194Google Scholar
  107. 107.
    Zuidema E, van Leeuwen PWNM, Bo C (2005) Reductive elimination of organic molecules from palladium-diphosphine complexes. Organometallics 24:3703–3710Google Scholar
  108. 108.
    Ananikov VP, Musaev DG, Morokuma K (2007) Critical effect of phosphane ligands on the mechanism of carbon-carbon bond formation involving palladium(II) complexes: a theoretical investigation of reductive elimination from square-planar and T-shape species. Eur J Inorg Chem 5390–5399Google Scholar
  109. 109.
    Ariafard A, Yates BF (2009) In-depth insight into the electronic and steric effects of phosphine ligands on the mechanism of the R–R reductive elimination from (PR3)2PdR2. J Organomet Chem 694:2075–2084Google Scholar
  110. 110.
    Watson L, Eisenstein O (2002) Entropy explained: the origin of some simple trends. J Chem Educ 79:1269–1277Google Scholar
  111. 111.
    Perez-Rodriguez M, Braga AAC, Garcia-Melchor M, Perez-Temprano M, Casares JA, Ujaque G, de Lera AR, Alvarez R, Maseras F, Espinet P (2009) C–C reductive elimination in palladium complexes, and the role of coupling additives A DFT study supported by experiment. J Am Chem Soc 131(10):3650–3655Google Scholar

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© Springer Science+Business Media B.V. 2011

Authors and Affiliations

  • Max García-Melchor
    • 1
  • Gregori Ujaque
    • 1
  • Feliu Maseras
    • 1
    • 2
  • Agustí Lledós
    • 1
  1. 1.Departament de Química, Edifici CnUniversitat Autònoma de BarcelonaBellaterraSpain
  2. 2.Institute of Chemical Research of Catalonia (ICIQ)TarragonaSpain

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