NHC-copper(I) bifluoride complexes: "auto-activating" catalysts

Journal of Organometallic Chemistry

Volumn 730, Issue , 2013, Pages 95-103

  Vergote, Thomas ^a   Nahra, Fady ^a   Peeters, Daniel ^a   Riant, Olivier ^a   Leyssens, Tom ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Catalysis; Copper(I); DFT; Hydrosilylation; N Heterocyclic diaminocarbene; Reactivity

Indexed keywords

ACTIVATING AGENTS; ACTIVATION MECHANISMS; COPPER (I) COMPLEXES; DFT; HYDRIDE FORMATION; N-HETEROCYCLIC; THEORETICAL AND EXPERIMENTAL; THEORETICAL RESULT;

CATALYSIS; CATALYSTS; CHEMICAL ACTIVATION; HYDRIDES; HYDROSILYLATION; KETONES; REACTIVITY (NUCLEAR);

COPPER;

EID: 84875901203     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2012.10.011     Document Type: Conference Paper

References (63)

1. T. Vergote, F. Nahra, A. Welle, M. Luhmer, J. Wouters, N. Mager, O. Riant, and T. Leyssens Chem. Eur. J. 18 2012 793 798
2. J.R. Herron, and Z.T. Ball J. Am. Chem. Soc. 130 2008 16486 16487
3. J.R. Herron, V. Russo, E.J. Valente, and Z.T. Ball Chem. Eur. J. 15 2009 8713 8716
4. V. Russo, J.R. Herron, and Z.T. Ball Org. Lett. 12 2010 220 223
5. D.S. Laitar, Ph.D. thesis, Massachusetts Institute of Technology, Cambridge, 2006.
6. T. Fujihara, T. Xu, K. Semba, J. Terao, and Y. Tsuji Angew. Chem. Int. Ed. 50 2011 523 527
7. O. Riant, N. Mostefaï, and J. Courmarcel Synthesis 18 2004 2943 2958
8. S. Sirol, J. Courmarcel, N. Mostefaï, and O. Riant Org. Lett. 3 2001 4111 4113
9. J. Courmarcel, N. Mostefaï, S. Sirol, S. Choppin, and O. Riant Isr. J. Chem. 41 2001 231 240
10. N. Mostefaï, S. Sirol, J. Courmarcel, and O. Riant Synthesis 8 2007 1265 1271
11. W.S. Mahoney, D.M. Brestensky, and J.M. Stryker J. Am. Chem. Soc. 110 1988 291 293
12. S. Dìez-González, E.D. Stevens, N.M. Scott, J.L. Petersen, and S.P. Nolan Chem. Eur. J. 14 2008 158 168
13. H. Kaur, F.K. Zinn, E.D. Stevens, and S.P. Nolan Organometallics 23 2004 1157 1160
14. A. Albright, and R.E. Gawley J. Am. Chem. Soc. 2011 19680 19683
15. S. Dìez-González, H. Kaur, F.K. Zinn, E.D. Stevens, and S.P. Nolan J. Org. Chem. 70 2005 4784 4796
16. S. Dìez-González, and S.P. Nolan Acc. Chem. Res. 41 2008 349 358
17. S. Dìez-González, and S.P. Nolan Aldrichim. Acta 41 2008 43 51
18. O. Riant Copper(I) hydride reagents and catalysts Z. Rappoport, I. Marek, The Chemistry of Organocopper Compounds 2009 Wiley & Sons Ltd 731 773
19. T. Gathy, D. Peeters, and T. Leyssens J. Organomet. Chem. 694 2009 3943 3950
20. J.T. Issenhuth, F.P. Notter, S. Dagorne, A. Dedieu, and S. Bellemin-Laponnaz Eur. J. Inorg. Chem. 2010 499 503
21. T. Gathy, O. Riant, D. Peeters, and T. Leyssens J. Organomet. Chem. 696 2011 3425 3430
22. T. Gathy, T. Leyssens, and D. Peeters Comp. Theor. Chem. 970 2011 23 29
23. W. Zhang, W. Li, and S. Qin Org. Biomol. Chem. 10 2012 597 604
24. For DFT studies with NHCs, see: T.Vergote, T.Gathy, F.Nahra, O.Riant, D.Peeters, T.Leyssens, Theor. Chem. Acc. 131(2012) 1253-1265.
25. D.-w. Lee, and J. Yun Tetrahedron Lett. 45 2004 5415 5417
26. B.H. Lipshutz Copper(I)-mediated 1,2- and 1,4-reductions N. Krause, Modern Organocopper Chemistry 2002 Wiley-VCH Weinheim 167 187
27. A.D. Becke J. Chem. Phys. 98 1993 5648 5653
28. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
29. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, 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, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision C.02 2004 Gaussian, Inc. Wallingford CT
30. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 270 283
31. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 284 298
32. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 299 310
33. W.J. Hehre, R. Ditchfield, and J.A. Pople J. Chem. Phys. 56 1972 2257 2261
34. P.C. Hariharan, and J.A. Pople Theor. Chim. Acta 28 1973 213 222
35. J.P. Foster, and F. Weinhold J. Am. Chem. Soc. 102 1980 7211 7218
36. A.E. Reed, and F. Weinhold J. Chem. Phys. 78 1983 4066 4073
37. A.E. Reed, R.B. Weinstock, and F. Weinhold J. Chem. Phys. 83 1985 735 746
38. A.E. Reed, and F. Weinhold J. Chem. Phys. 83 1985 1736 1740
39. G. Saielli, K.C. Nicolaou, A. Ortiz, H. Zhang, and A. Bagno J. Am. Chem. Soc. 133 2011 6072 6077
40. F. Rastrelli, and A. Bagno Chem. Eur. J. 15 2009 7990 8004
41. P. Tahtinen, G. Saielli, G. Guella, I. Mancini, and A. Bagno Chem. Eur. J. 14 2008 10445 10452
42. D. Tapu, D.A. Dixon, and C. Roe Chem. Rev. 109 2009 3385 3407
43. M.T. Cancès, B. Mennucci, and J. Tomasi J. Chem. Phys. 107 1997 3032 3041
44. M. Cossi, V. Barone, B. Mennucci, and J. Tomasi Chem. Phys. Lett. 286 1998 253 260
45. B. Mennucci, and J. Tomasi J. Chem. Phys. 106 1997 5151 5158 this method is selected with the keyword «PCM» in Gaussian 03
46. T. Kupka Magn. Reson. Chem. 46 2008 851 858
47. A. Bagno, and G. Saielli Theor. Chem. Acc. 117 2007 603 619
48. A. Bagno, F. Rastrelli, and G. Saielli Chem. Eur. J. 12 2006 5514 5525
49. M.G. Chini, R. Riccio, and G. Bifulco Magn. Reson. Chem. 46 2008 962 968
50. J.A. Tang, B.D. Ellis, T.H. Warren, J.V. Hanna, C.L.B. Macdonald, and R.W. Schurko J. Am. Chem. Soc. 129 2007 13049 13065
51. B.H. Lipshutz, W. Chrisman, K. Noson, P. Papa, J.A. Sclafani, R.W. Vivian, and J.M. Keith Tetrahedron 56 2000 2779 2788
52. N.P. Mankad, D.S. Laitar, and J.P. Sadighi Organometallics 23 2004 3369 3371
53. T. Keith, and J. Millam Gaussview, Version 4.1.2, R. Dennington, II 2006 Semichem, Inc. Shawnee
54. R.R. Holmes Chem. Rev. 90 1990 17 31
55. K. Oisaki, D. Zhao, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 128 2006 7164 7165
56. K. Oisaki, Y. Suto, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 125 2003 5644 5645
57. Y. Suto, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 129 2007 500 501
58. S.Yamasaki, K.Fujii, R.Wada, M.Kanai, M.Shibasaki, J. Am. Chem. Soc. 124(2002) 6536-6537.
59. C.J. Handy, Y.F. Lam, and P. DeShong J. Org. Chem. 65 2000 3542 3543
60. S. Yamaguchi, S. Akiyama, and K. Tamao Organometallics 18 1999 2851 2854
61. P.D. Prince, M.J. Bearpark, G.S. McGrady, and J.W. Steed Dalton Trans. 2008 271 282
62. Y. Kim, M. Kim, and F.P. Gabbaï Org. Lett. 12 2010 600 602
63. A. Kawachi, A. Tani, J. Shimada, and Y. Yamamoto J. Am. Chem. Soc. 130 2008 4222 4223