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The importance of conformational search: a test case on the catalytic cycle of the Suzuki–Miyaura cross-coupling

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Abstract

Conformational diversity is an often neglected aspect in computational studies of transition metal complexes, even when relatively large systems are involved. The importance of conformational searches is illustrated through the analysis of the errors that could be caused by a wrong choice of conformers in the computational study of the Suzuki–Miyaura cross-coupling between CH2=CHBr and CH2=CHB(OH)2 catalyzed by [(PPh3)2Pd] or [(P(i-Pr)3)2Pd]. The error bars associated with conformational diversity of the [(PPh3)2Pd] catalyst range between 0.3 and 6.7 kcal/mol, the values growing up to 11.4 kcal/mol when the more flexible [(P(i-Pr)3)2Pd] catalyst is considered.

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References

  1. Schwabe T, Grimme S (2008) Acc Chem Res 41:569

    Article  CAS  Google Scholar 

  2. Bühl M, Reimann C, Pantazis DA, Bredow T, Neese F (2008) J Chem Theory Comput 4:1449

    Article  Google Scholar 

  3. Sousa SF, Fernandes PA, Ramos MJ (2007) J Phys Chem A 111:10439

    Article  CAS  Google Scholar 

  4. Rappe AK, Colwell KS, Casewit CJ (1993) Inorg Chem 32:3438

    Article  CAS  Google Scholar 

  5. Comba P, Remenyi R (2003) Coord Chem Rev 238:9

    Article  Google Scholar 

  6. Norrby PO, Brandt P (2001) Coord Chem Rev 212:79

    Article  CAS  Google Scholar 

  7. Deeth RJ (2008) Inorg Chem 47:6711

    Article  CAS  Google Scholar 

  8. Sabolovic J, Gomzi V (2009) J Chem Theory Comp 5:1940

    Article  CAS  Google Scholar 

  9. Tubert-Brohman I, Schmid M, Meuwly M (2009) J Chem Theory Comp 5:530

    Article  CAS  Google Scholar 

  10. Feldgus S, Landis CR (2000) J Am Chem Soc 122:12714

    Article  CAS  Google Scholar 

  11. Landis CR, Feldgus S (2000) Angew Chem Int Ed 39:2863

    Article  CAS  Google Scholar 

  12. Feldgus S, Landis CR (2001) Organometallics 20:2374

    Article  CAS  Google Scholar 

  13. Ujaque G, Maseras F, Lledós A (1997) J Org Chem 62:7892

    Article  CAS  Google Scholar 

  14. Ujaque G, Maseras F, Lledós A (1999) J Am Chem Soc 121:1317

    Article  CAS  Google Scholar 

  15. Balcells D, Drudis-Sole G, Besora M, Dolker N, Ujaque G, Maseras F, Lledós A (2003) Faraday Discuss 124:429

    Article  CAS  Google Scholar 

  16. Fey N (2010) Dalton Trans 39:296

    CAS  Google Scholar 

  17. Miyaura N, Yamada K, Suginome H, Suzuki A (1985) J Am Chem Soc 107:972

    Article  CAS  Google Scholar 

  18. Miyaura N, Suzuki A (1995) Chem Rev 95:2457

    Article  CAS  Google Scholar 

  19. Suzuki A (2002) J Organomet Chem 653:83

    Article  CAS  Google Scholar 

  20. Christmann U, Vilar R (2005) Angew Chem Int Ed 44:366

    Article  CAS  Google Scholar 

  21. Braga AAC, Ujaque G, Maseras F (2008) In: Musaev DG, Morokuma K (Org) Computational modeling for homogeneous and enzymatic catálysis: a knowledge-base for designing efficient catalysts. Wiley-VCH, Hoboken, NJ, pp 109–130

  22. Molander GA, Canturk B (2009) Angew Chem Int Ed 48:9240

    Article  CAS  Google Scholar 

  23. Xue L, Lin Z (2010) Chem Soc Rev 39:1692

    Article  CAS  Google Scholar 

  24. Littke AF, Fu GC (2002) Angew Chem Int Ed 41:4176

    Article  CAS  Google Scholar 

  25. Barrios-Landeros L, Hartwig JF (2005) J Am Chem Soc 127:6944

    Article  CAS  Google Scholar 

  26. Kozuch S, Amatore C, Jutand A, Shaik S (2005) Organometallics 24:2319

    Article  CAS  Google Scholar 

  27. Ahlquist M, Norrby PO (2007) Organometallics 26:550

    Article  CAS  Google Scholar 

  28. Gourlaouen C, Ujaque G, Lledós A, Medio-Simón M, Asensio G, Maseras F (2009) J Org Chem 74:4049

    Article  CAS  Google Scholar 

  29. Miyaura N (2002) J Organomet Chem 653:54

    Article  CAS  Google Scholar 

  30. Gooßen LJ, Koley D, Hermann HL, Thiel W (2005) J Am Chem Soc 127:11102

    Article  Google Scholar 

  31. Sicre C, Braga AAC, Maseras F, Cid MM (2008) Tetrahedron 64:7437

    Article  CAS  Google Scholar 

  32. Ananikov VP, Musaev DG, Morokuma K (2005) Organometallics 24:715

    Article  CAS  Google Scholar 

  33. Hartwig JF (2007) Inorg Chem 46:1936

    Article  CAS  Google Scholar 

  34. Ananikov VP, Musaev DG, Morokuma K (2007) Eur J Inorg Chem 2007:5390

    Article  Google Scholar 

  35. Pérez-Rodríguez M, Braga AAC, Garcia-Melchor M, Pérez-Temprano MH, Casares JA, Ujaque G, de Lera AR, Álvarez R, Maseras F, Espinet P (2009) J Am Chem Soc 131:3650

    Article  Google Scholar 

  36. Hartwig JF, Paul F (1995) J Am Chem Soc 117:5373

    Article  CAS  Google Scholar 

  37. Schoenebeck F, Houk KN (2010) J Am Chem Soc 132:2496

    Article  CAS  Google Scholar 

  38. Ariafard A, Yates BF (2009) J Organomet Chem 694:1075

    Article  Google Scholar 

  39. Ariafard A, Yates BF (2009) J Am Chem Soc 131:13981

    Article  CAS  Google Scholar 

  40. Braga AAC, Ujaque G, Maseras F (2006) Organometallics 25:3647

    Article  CAS  Google Scholar 

  41. Braga AAC, Morgon NH, Ujaque G, Maseras F (2005) J Am Chem Soc 127:9298

    Article  CAS  Google Scholar 

  42. Braga AAC, Morgon NH, Ujaque G, Lledós A, Maseras F (2006) J Organomet Chem 691:4459

    Article  CAS  Google Scholar 

  43. Mohamadi F, Richards NGJ, Guida WC, Liskamp R, Lipton M, Caufield C, Chang G, Hendrickson T, Still WC (1990) J Comp Chem 11:440

    Article  CAS  Google Scholar 

  44. Chang G, Guida WC, Still WC (1989) J Am Chem Soc 111:4379

    Article  CAS  Google Scholar 

  45. Saunders M, Houk KN, Wu YD, Still WC, Lipton M, Chang G, Guida WC (1990) J Am Chem Soc 112:1419

    Article  CAS  Google Scholar 

  46. Allinger NL, Yuh YH, Lii JH (1989) J Am Chem Soc 111:8551

    Article  CAS  Google Scholar 

  47. Shenkin PS, McDonald DQ (1994) J Comp Chem 15:899

    Article  CAS  Google Scholar 

  48. Maseras F, Morokuma K (1995) J Comp Chem 16:1170

    Article  CAS  Google Scholar 

  49. Vreven T, Morokuma K (2000) J Comp Chem 21:1419

    Article  CAS  Google Scholar 

  50. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JJA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Revision C.02 ed. Gaussian, Inc., Wallingford, CT

    Google Scholar 

  51. Lee CT, Yang WT, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  52. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  53. Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ (1994) J Phys Chem 98:11623

    Article  CAS  Google Scholar 

  54. Hehre WJ, Ditchfield R, Pople JA (1972) J Chem Phys 56:2257

    Article  CAS  Google Scholar 

  55. Hariharan PC, Pople JÁ (1973) Theor Chim Acta 28:213

    Article  CAS  Google Scholar 

  56. Francl MM, Pietro WJ, Hehre WJ, Binkley JS, Gordon MS, Defrees DJ, Pople JA (1982) J Chem Phys 77:3654

    Article  CAS  Google Scholar 

  57. Dunning TH Jr, Hay PJ (1977) In: Schaefer III, HF (ed) Methods of electronic structure theory, vol 3. Plenum, New York, pp 1–28

  58. Igelmann G, Stoll H, Preuss H (1988) Mol Phys 65:1321

    Article  CAS  Google Scholar 

  59. Andrae D, Haussermann U, Dolg M, Stoll H, Preuss H (1990) Theor Chim Acta 77:123

    Article  CAS  Google Scholar 

  60. Bergner A, Dolg M, Kuchle W, Stoll H, Preuss H (1993) Mol Phys 80:1431

    Article  CAS  Google Scholar 

  61. Rappe AK, Casewit CJ, Colwell KS, Goddard WA, Skiff WM (1992) J Am Chem Soc 114:10024

    Article  CAS  Google Scholar 

  62. Casado AL, Espinet P (1998) Organometallics 17:954

    Article  CAS  Google Scholar 

  63. Tolman CA (1977) Chem Rev 77:313

    Article  CAS  Google Scholar 

  64. Eremenko IL, Nefedov SE, Veghini DA, Rosenberger ST, Berke H, Ol’shnitskaya IA, Novotortsev VM (1997) Russ Chem Bull 46:137

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank the ICIQ foundation, the Spanish Ministerio de Ciencia e Innovacion (Consolider Ingenio 2010 CSD2006-0003 and CSD2007-000006; projects CTQ2008-06866-CO2-01/BQU, CTQ2008-06866-CO2-02/BQU, FEDER support), Generalitat de Catalunya (Grants 2009SGR0259 and XRQTC). M. B. thanks the Spanish Ministerio de Ciencia e Innovacion for a “Juan de la Cierva” grant.

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Authors and Affiliations

  1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007, Tarragona, Catalonia, Spain

    Maria Besora, Ataualpa A. C. Braga & Feliu Maseras

  2. Departament de Química, Edifici Cn, Universitat Autònoma de Barcelona, 08193, Bellaterra, Catalonia, Spain

    Gregori Ujaque, Feliu Maseras & Agustí Lledós

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  1. Maria Besora
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  2. Ataualpa A. C. Braga
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  3. Gregori Ujaque
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  4. Feliu Maseras
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  5. Agustí Lledós
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Correspondence to Feliu Maseras or Agustí Lledós.

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Published as part of the special issue celebrating theoretical and computational chemistry in Spain.

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Besora, M., Braga, A.A.C., Ujaque, G. et al. The importance of conformational search: a test case on the catalytic cycle of the Suzuki–Miyaura cross-coupling. Theor Chem Acc 128, 639–646 (2011). https://doi.org/10.1007/s00214-010-0823-6

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