C-F bond breaking through aromatic nucleophilic substitution with a hydroxo ligand mediated via water bifunctional activation

Bulletin of the Chemical Society of Japan

Volumn 86, Issue 5, 2013, Pages 557-568

  Dub, Pavel A ^a   Wang, Hui ^a   Matsunami, Asuka ^a   Gridnev, Ilya D ^a   Kuwata, Shigeki ^a   Ikariya, Takao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC NUCLEOPHILIC SUBSTITUTION; COMPUTATIONAL ANALYSIS; DENSITY FUNCTIONAL THEORIES (DFT); DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; EXPERIMENTAL STUDIES; SIGNIFICANT DIFFERENCES; SINGLE-CRYSTAL X-RAY DIFFRACTION STUDIES;

CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; IRIDIUM; IRIDIUM COMPOUNDS; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RUBIDIUM COMPOUNDS; RUTHENIUM; RUTHENIUM COMPOUNDS; STEREOSELECTIVITY; SULFUR DIOXIDE; X RAY DIFFRACTION;

CHLORINE COMPOUNDS;

EID: 84878874207     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.20120359     Document Type: Article

References (63)

1. Bifunctional Molecular Catalysis in Topicsin Organometallic Chemistry, ed. by T. Ikariya, M. Shibasaki, Springer-Verlag, Berlin, 2011, Vol. 37. doi:10.1007/978-3-642-20731-0.
2. P. A. Dub, T. Ikariya, ACS Catal. 2012, 2, 1718.
3. T. Ikariya, Bull. Chem. Soc. Jpn. 2011, 84, 1.
4. T. Ikariya, I. D. Gridnev, Top. Catal. 2010, 53, 894.
5. T. Ikariya, I. D. Gridnev, Chem. Rec. 2009, 9, 106.
6. T. Ikariya, A. J. Blacker, Acc. Chem. Res. 2007, 40, 1300.
7. T. Ikariya, K. Murata, R. Noyori, Org. Biomol. Chem. 2006, 4, 393.
8. J. S. M. Samec, J.-E. Bäckvall, P. G. Andersson, P. Brandt, Chem. Soc. Rev. 2006, 35, 237.
9. S. E. Clapham, A. Hadzovic, R. H. Morris, Coord. Chem. Rev. 2004, 248, 2201.
10. R. Noyori, Adv. Synth. Catal. 2003, 345, 15.
11. S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 7562.
12. A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521.
13. K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
14. K. Murata, T. Ikariya, R. Noyori, J. Org. Chem. 1999, 64, 2186.
15. K. Murata, K. Okano, M. Miyagi, H. Iwane, R. Noyori, T. Ikariya, Org. Lett. 1999, 1, 1119.
16. M. Watanabe, K. Murata, T. Ikariya, J. Org. Chem. 2002, 67, 1712.
17. T. Hamada, T. Torii, K. Izawa, R. Noyori, T. Ikariya, Org. Lett. 2002, 4, 4373.
18. K. Okano, K. Murata, T. Ikariya, Tetrahedron Lett. 2000, 41, 9277.
19. T. Koike, K. Murata, T. Ikariya, Org. Lett. 2000, 2, 3833.
20. N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 4916.
21. T. Touge, T. Hakamata, H. Nara, T. Kobayashi, N. Sayo, T. Saito, Y. Kayaki, T. Ikariya, J. Am. Chem. Soc. 2011, 133, 14960.
22. P. A. Dub, H. Wang, M. Watanabe, I. D. Gridnev, T. Ikariya, Tetrahedron Lett. 2012, 53, 3452.
23. I. D. Gridnev, M. Watanabe, H. Wang, T. Ikariya, J. Am. Chem. Soc. 2010, 132, 16637.
24. H. Wang, M. Watanabe, T. Ikariya, Tetrahedron Lett. 2005, 46, 963.
25. T. Ikariya, H. Wang, M. Watanabe, K. Murata, J. Organomet. Chem. 2004, 689, 1377.
26. M. Watanabe, K. Murata, T. Ikariya, J. Am. Chem. Soc. 2003, 125, 7508.
27. M. Watanabe, A. Ikagawa, H. Wang, K. Murata, T. Ikariya, J. Am. Chem. Soc. 2004, 126, 11148.
28. Y. Hasegawa, M. Watanabe, I. D. Gridnev, T. Ikariya, J. Am. Chem. Soc. 2008, 130, 2158.
29. Y. Hasegawa, I. D. Gridnev, T. Ikariya, Bull. Chem. Soc. Jpn. 2012, 85, 316.
30. Y. Hasegawa, I. D. Gridnev, T. Ikariya, Angew. Chem., Int. Ed. 2010, 49, 8157.
31. S. Arita, T. Koike, Y. Kayaki, T. Ikariya, Angew. Chem., Int. Ed. 2008, 47, 2447.
32. S. Kamezaki, S. Akiyama, Y. Kayaki, S. Kuwata, T. Ikariya, Tetrahedron: Asymmetry 2010, 21, 1169.
33. A. Nova, R. Mas-Ballesté, A. Lledós, Organometallics 2012, 31, 1245.
34. E. Clot, O. Eisenstein, N. Jasim, S. A. Macgregor, J. E. McGrady, R. N. Perutz, Acc. Chem. Res. 2011, 44, 333.
35. M. A. Bennett, A. K. Smith, J. Chem. Soc., Dalton Trans. 1974, 233.
36. Synthesis of Organometallic Compounds: A Practical Guide, ed. by S. Komiya, Wiley, 2002.
37. J. W. Kang, K. Moseley, P. M. Maitlis, J. Am. Chem. Soc. 1969, 91, 5970.
38. W. Kohn, L. J. Sham, Phys. Rev. 1965, 140, A1133.
39. P. Hohenberg, W. Kohn, Phys. Rev. 1964, 136, B864.
40. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
41. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09 (Revision C.01), Gaussian, Inc., Wallingford CT, 2009.
42. http://www.gsic.titech.ac.jp/en.
43. M. Cossi, N. Rega, G. Scalmani, V. Barone, J. Comput. Chem. 2003, 24, 669.
44. K. Fukui, Acc. Chem. Res. 1981, 14, 363.
45. E. F. Pettersen, T. D. Goddard, C. C. Huang, G. S. Couch, D. M. Greenblatt, E. C. Meng, T. E. Ferrin, J. Comput. Chem. 2004, 25, 1605.
46. J. Carlsson, J. Åqvist, J. Phys. Chem. B 2005, 109, 6448.
47. C.-E. Chang, W. Chen, M. K. Gilson, J. Chem. Theory Comput. 2005, 1, 1017.
48. N. Singh, A. Warshel, J. Phys. Chem. B 2009, 113, 7372.
49. P. A. Dub, R. Poli, J. Mol. Catal. A: Chem. 2010, 324, 89.
50. S. Kozuch, S. E. Lee, S. Shaik, Organometallics 2009, 28, 1303.
51. A. A. C. Braga, G. Ujaque, F. Maseras, Organometallics 2006, 25, 3647.
52. D. Ardura, R. López, T. L. Sordo, J. Phys. Chem. B 2005, 109, 23618.
53. B. O. Leung, D. L. Reid, D. A. Armstrong, A. Rauk, J. Phys. Chem. A 2004, 108, 2720.
54. J. Cooper, T. Ziegler, Inorg. Chem. 2002, 41, 6614.
55. S. Kozuch, S. Shaik, Acc. Chem. Res. 2011, 44, 101.
56. K. Stanley, M. C. Baird, J. Am. Chem. Soc. 1975, 97, 6598.
57. C. Lecomte, Y. Dusausoy, J. Protas, J. Tirouflet, A. Dormond, J. Organomet. Chem. 1974, 73, 67.
58. P. Espinet, J. A. Casares, in Fluxional Organometallic and Coordination Compounds in Physical Organometallic Chemistry, ed. by M. Gielen, R. Willem, B. Wrackmeyer, John Wiley & Sons, Ltd., 2004, Vol. 4, p. 131. doi:10.1002/0470858451.ch4.
59. P. A. Dub, T. Ikariya, et al., manuscript in preparation.
60. M. J. S. Dewar, J. Am. Chem. Soc. 1984, 106, 209.
61. S. Akiyama, Y. Kayaki, T. Ikariya, Abstr. Symp. Coord. Chem. Jpn., 58, 23A09, 2005.
62. X. Wu, J. Liu, D. Di Tommaso, J. A. Iggo, C. R. A. Catlow, J. Bacsa, J. Xiao, Chem.-Eur. J. 2008, 14, 7699.
63. O. V. Ozerov, Chem. Soc. Rev. 2009, 38, 83.