Combined experimental and computational investigations of rhodium- and ruthenium-catalyzed C-H functionalization of pyrazoles with alkynes

Journal of Organic Chemistry

Volumn 79, Issue 5, 2014, Pages 1954-1970

  Algarra, Andrés G ^a   Cross, Warren B ^b,c   Davies, David L ^b   Khamker, Qudsia ^b   Macgregor, Stuart A ^a   McMullin, Claire L ^a   Singh, Kuldip ^b  

^a HERIOT WATT UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

^c NOTTINGHAM TRENT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

C-H FUNCTIONALIZATION; COMPUTATIONAL INVESTIGATION; COMPUTATIONAL STUDIES; EXPERIMENTAL SYSTEM; MIGRATORY INSERTION; N-H AND C-H BOND ACTIVATIONS; RATE-LIMITING PROCESS; REDUCTIVE COUPLINGS;

ACTIVATION ANALYSIS; CATALYSIS; CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; ISOTOPES; RHODIUM; VOLATILE FATTY ACIDS;

HYDROCARBONS;

ACETIC ACID; ALKYNE; ISOTOPE; PYRAZOLE DERIVATIVE; RHODIUM; RUTHENIUM;

ARTICLE; CATALYSIS; CATALYST; DENSITY FUNCTIONAL THEORY; DISPERSION; HYDROGEN BOND; PROTON TRANSPORT; REACTION OPTIMIZATION; REDUCTION;

EID: 84896767022     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402592z     Document Type: Article

References (74)

1. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
2. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
3. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
4. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2009, 110, 624
5. Bellina, F.; Rossi, R. Chem. Rev. 2009, 110, 1082
6. Ackermann, L. Chem. Rev. 2011, 111, 1315
7. Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754
8. Davies, D. L.; Donald, S. M. A.; Al-Duaij, O.; Fawcett, J.; Little, C.; Macgregor, S. A. Organometallics 2006, 25, 5976
9. Davies, D. L.; Donald, S. M. A.; Al-Duaij, O.; Macgregor, S. A.; Polleth, M. J. Am. Chem. Soc. 2006, 128, 4210
10. Boutadla, Y.; Davies, D. L.; Macgregor, S. A.; Poblador-Bahamonde, A. I. Dalton Trans. 2009, 5820
11. Boutadla, Y.; Davies, D. L.; Macgregor, S. A.; Poblador-Bahamonde, A. I. Dalton Trans. 2009, 5887
12. Musashi, Y.; Sakaki, S. J. Am. Chem. Soc. 2000, 122, 3867
13. Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066
14. Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496
15. Ackermann, L.; Vicente, R.; Althammer, A. Org. Lett. 2008, 10, 2299
16. Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754
17. Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848
18. Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407
19. Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362
20. Shimizu, M.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 3478
21. Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 6295
22. Fukutani, T.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. Chem. Commun. 2009, 5141
23. Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7094
24. Umeda, N.; Tsurugi, H.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2008, 47, 4019
25. Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474
26. Guimond, N.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 12050
27. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
28. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
29. Li, L.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414
30. Li, L.; Brennessel, W. W.; Jones, W. D. Organometallics 2009, 28, 3492
31. Sortais, J. B.; Pannetier, N.; Holuigue, A.; Barloy, L.; Sirlin, C.; Pfeffer, M.; Kyritsakas, N. Organometallics 2007, 26, 1856
32. Boutadla, Y.; Al-Duaij, O.; Davies, D. L.; Griffith, G. A.; Singh, K. Organometallics 2009, 28, 433
33. Boutadla, Y.; Davies, D. L.; Al-Duaij, O.; Fawcett, J.; Jones, R. C.; Singh, K. Dalton Trans. 2010, 39, 10447
34. Davies, D. L.; Al-Duaij, O.; Fawcett, J.; Giardiello, M.; Hilton, S. T.; Russell, D. R. Dalton Trans. 2003, 4132
35. Li, L.; Jiao, Y.; Brennessel, W. W.; Jones, W. D. Organometallics 2010, 29, 4593
36. Han, Y.-F.; Li, H.; Hu, P.; Jin, G.-X. Organometallics 2011, 30, 905
37. Li, B.; Feng, H. L.; Wang, N. A. C.; Ma, J. F.; Song, H. B.; Xu, S. S.; Wang, B. Q. Chem.-Eur. J. 2012, 18, 12873
38. Wang, N.; Li, B.; Song, H.; Xu, S.; Wang, B. Chem.-Eur. J. 2013, 19, 358
39. Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 3066
40. A DFT study of Rh(III)-catalyzed oxidative Heck coupling of phenol carbamates with alkenes has recently appeared; see: Zhang, Q.; Yu, H.-Z.; Li, Y.-T.; Liu, L.; Huang, Y.; Fu, Y. Dalton Trans. 2013, 42, 4175
41. Quiñones, N.; Seoane, A.; García-Fandiño, R.; Mascareñas, J. L.; Gulías, M. Chem. Sci. 2013, 4, 2874
42. Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449
43. Xu, L.; Zhu, Q.; Huang, G.; Cheng, B.; Xia, Y. J. Org. Chem. 2012, 77, 3017
44. Umeda, N.; Hirano, K.; Satoh, T.; Shibata, N.; Sato, H.; Miura, M. J. Org. Chem. 2011, 76, 13
45. Li, X.; Zhao, M. J. Org. Chem. 2011, 76, 8530
46. Ma, W.; Graczyk, K.; Ackermann, L. Org. Lett. 2012, 14, 6318
47. Clar, E. Polycyclic Hydrocarbons; Academic Press: London, 1964.
48. Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2068
49. Wang, H.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 7318
50. Ahlquist, M. S. G.; Norrby, P. O. Angew. Chem., Int. Ed. 2011, 50, 11794
51. Minenkov, Y.; Occhipinti, G.; Jensen, V. R. J. Phys. Chem. A 2009, 113, 11833
52. Ryde, U.; Mata, R. A.; Grimme, S. Dalton Trans. 2011, 40, 11176
53. Sieffert, N.; Bühl, M. Inorg. Chem. 2009, 48, 4622
54. Zhao, Y.; Truhlar, D. G. Org. Lett. 2007, 9, 1967
55. Bennett, M. A.; Macgregor, S. A.; Wenger, E. Helv. Chim. Acta 2001, 84, 3084
56. Edwards, A. J.; Macgregor, S. A.; Rae, A. D.; Wenger, E.; Willis, A. C. Organometallics 2001, 20, 2864
57. Macgregor, S. A.; Wenger, E. Organometallics 2002, 21, 1278
58. White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1977, 1654
59. Pleier, A. K.; Glas, H.; Grosche, M.; Sirsch, P.; Thiel, W. R. Synthesis 2001, 55
60. Texierboullet, F.; Klein, B.; Hamelin, J. Synthesis 1986, 409
61. Guillou, S.; Bonhomme, F. J.; Ermolenko, M. S.; Janin, Y. L. Tetrahedron 2011, 67, 8451
62. Li, J.-H.; Liang, Y.; Xie, Y.-X. J. Org. Chem. 2005, 70, 4393
63. Bruker; Version 6.10 ed.; Bruker Inc., Madison, WI, 1998-2000.
64. Vandersluis, P.; Spek, A. L. Acta Crystallogr., Sect. A 1990, 46, 194
65. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565
66. Frisch, M. J. Gaussian, Inc., Wallingford, CT, 2004.
67. Frisch, M. J. Gaussian, Inc., Wallingford, CT, 2009.
68. Andrae, D.; Häußermann, U.; Dolg, M.; Stoll, H.; Preuß, H. Theor. Chim. Acta 1990, 77, 123
69. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213
70. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257
71. Becke, A. D. Phys. Rev. A 1988, 38, 3098
72. Perdew, J. P. Phys. Rev. B 1986, 33, 8822
73. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
74. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132