Kinetic and computational studies on Pd(I) dimer-mediated halogen exchange of aryl iodides

Journal of Organic Chemistry

Volumn 79, Issue 24, 2014, Pages 12041-12046

  Kalvet, Indrek ^a   Bonney, Karl J ^a   Schoenebeck, Franziska ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; DISPERSIONS; FREE ENERGY; KINETICS;

ACTIVATION BARRIERS; ACTIVATION FREE ENERGY; COMPUTATIONAL STUDIES; FIRST ORDER KINETICS; HALOGEN EXCHANGE; KINETIC STUDY; QUANTITATIVE PREDICTION; REACTION PATHWAYS;

IODINE;

DIMER; HALOGEN; IODINE DERIVATIVE; PALLADIUM;

ARTICLE; CALCULATION; CONCENTRATION (PARAMETERS); DISPERSION; ENTHALPY; ENTROPY; KINETICS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TEMPERATURE; THERMODYNAMICS;

EID: 84919626248     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501889j     Document Type: Article

References (50)

1. Chem. Sci. 2013, 4, 4434
2. Negishi, E.-I. and de Meijere, A., Eds. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley: New York, 2002.
3. Diederich, F. and de Meijere, A., Eds. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Wiley-VCH: Weinheim, 2004.
4. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
5. Negishi, E.-I. Acc. Chem. Res. 1982, 15, 340
6. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508
7. Knappke, C. E. I.; Jacobi von Wangelin, A. Chem. Soc. Rev. 2011, 40, 4948
8. Chinchilla, R.; Najera, C. Chem. Soc. Rev. 2011, 40, 5084
9. Seechurn, C. C. J.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062
10. The Nobel Prize in Chemistry 2010. http://www.nobelprize.org/nobel-prizes/chemistry/laureates/2010/press.pdf.
11. Bonney, K. J.; Schoenebeck, F. Chem. Soc. Rev. 2014, 43, 6609
12. Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824-889
13. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
14. Muñiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412
15. Hickman, A. J.; Sanford, M. S. Nature 2012, 484, 177
16. For a commentary, see: Paton, R. S.; Brown, J. M. Angew. Chem., Int. Ed. 2012, 51, 10448
17. For a review on dinuclear Pd complexes, see: Mirica, L. M.; Khusnutdinova, J. R. Coord. Chem. Rev. 2013, 257, 299
18. Colacot, T. J. Platinum Met. Rev. 2009, 53, 183
19. Markert, C.; Neuburger, M.; Kulicke, K.; Meuwly, M.; Pfaltz, A. Angew. Chem., Int. Ed. 2007, 46, 5892
20. Hill, L. L.; Crowell, J. L.; Tutwiler, S. L.; Massie, N. L.; Corey Hines, C.; Griffin, S. T.; Rogers, R. D.; Shaughnessy, K. H.; Grasa, G. A.; Seechurn, C. C. C. J.; Li, H.; Colacot, T. J.; Chou, J.; Woltermann, C. J. J. Org. Chem. 2010, 75, 6477
21. Bedford, R. B.; Haddow, M. F.; Mitchell, C. J.; Webster, R. L. Angew. Chem., Int. Ed. 2011, 50, 5524
22. Seechurn, C. C. C. J.; Parisel, S. L.; Colacot, T. J. J. Org. Chem. 2011, 76, 7918
23. First synthesis of 1: Vilar, R.; Mingos, D. M. P.; Cardin, C. J. J. Chem. Soc., Dalton Trans. 1996, 4313
24. Hruszkewycz, D. P.; Balcells, D.; Guard, L. M.; Hazari, N.; Tilset, M. J. Am. Chem. Soc. 2014, 136, 7300
25. Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746
26. Prashad, M.; Mak, X. Y.; Liu, Y.; Repic, O. J. Org. Chem. 2003, 68, 1163
27. Aufiero, M.; Proutière, F.; Schoenebeck, F. Angew. Chem., Int. Ed. 2012, 51, 7226
28. Hruszkewycz, D. P.; Wu, J.; Green, J. C.; Hazari, N.; Schmeier, T. J. Organometallics 2012, 31, 470
29. Hruszkewycz, D. P.; Wu, J.; Hazari, N.; Incarvito, C. D. J. Am. Chem. Soc. 2011, 133, 3280
30. Murahashi, T.; Takase, K.; Oka, M.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 14908
31. Hama, T.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 4976
32. Denmark, S. E.; Baird, J. D. Org. Lett. 2006, 8, 793
33. Barder, T. E. J. Am. Chem. Soc. 2006, 128, 898
34. Mamone, P.; Grüunberg, M. F.; Fromm, M.; Khan, B. A.; Gooßen, L. J. Org. Lett. 2012, 14, 3716
35. Christmann, U.; Pantazis, D. A.; Benet-Buchholz, J.; McGrady, J. E.; Maseras, F.; Vilar, R. J. Am. Chem. Soc. 2006, 128, 6376
36. Proutiere, F.; Aufiero, M.; Schoenebeck, F. J. Am. Chem. Soc. 2012, 134, 606
37. Jahn, U. Top. Curr. Chem. 2012, 320, 323-451
38. Manolikakes, G.; Knochel, P. Angew. Chem., Int. Ed. 2009, 48, 205-209
39. Bonney, K. J.; Proutière, F.; Schoenebeck, F. Chem. Sci. 2013, 4, 4434
40. Conducted in analogy to a report by North and co-workers: Belokon, Y. N.; Clegg, W.; Harrington, R. W.; Maleev, V. I.; North, M.; Omedes Pujol, M.; Usanov, D. L.; Young, C. Chem.-Eur. J. 2009, 15, 2148
41. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Ö. Farkas; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2009.
42. Geometry was calculated at B3LYP/6-31G(d), with LANL2DZ for Pd, I.
43. Jacobsen, H.; Cavallo, L. ChemPhysChem 2012, 13, 562
44. Ronnholm, P.; Nilsson Lill, S. O.; Grafenstein, J.; Norrby, P.-O.; Pettersson, M.; Hilmersson, G. ChemPlusChem 2012, 77, 799
45. Grimme, S. ChemPhysChem 2012, 13, 1407
46. McMullin, C. L.; Jover, J.; Harvey, J. N.; Fey, N. Dalton Trans. 2010, 39, 10833
47. Iskra, J.; Stavber, S.; Zupan, M. Synthesis 2004, 1869
48. Kalgutkar, A. S.; Kozak, K. R.; Crews, B. C.; Hochgesang, G. P., Jr.; Marnett, L. J. J. Med. Chem. 1998, 41, 4800
49. Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456
50. Cramer, C. J. Essentials of Computational Chemistry: Theories and Models, 2nd ed.; Wiley: New York, 2004.