Intramolecular hydroalkoxylation and hydroamination of alkynes catalyzed by Cu(I) complexes supported by N-heterocyclic carbene ligands

ACS Catalysis

Volumn 2, Issue 10, 2012, Pages 2182-2193

  Pouy, Mark J ^a   Delp, Samuel A ^a   Uddin, Jamal ^b   Ramdeen, Vijay M ^a   Cochrane, Nikki A ^a   Fortman, George C ^a   Gunnoe, T Brent ^a   Cundari, Thomas R ^b   Sabat, Michal ^a   Myers, William H ^c  

^a UNIVERSITY OF VIRGINIA   (United States)

^b UNIVERSITY OF NORTH TEXAS   (United States)

^c UNIVERSITY OF RICHMOND   (United States)

Author keywords

Alkynes; Copper; Homogeneous catalysis; Hydroalkoxylation; N heterocyclic carbene

Indexed keywords

6-MEMBERED RINGS; ALKOXIDES; ALKYNE INSERTIONS; ALKYNES; ALKYNYLS; CATALYTIC REACTIONS; COPPER CATALYST; CU COMPLEXES; DFT STUDY; EXOCYCLIC METHYLENE GROUP; FIRST-ORDER; HIGH YIELD; HOMOGENEOUS CATALYSIS; HYDROALKOXYLATION; HYDROAMINATIONS; IMIDAZOL; INTRAMOLECULAR ADDITIONS; KINETIC STUDY; METHYL GROUP; N-HETEROCYCLIC CARBENE LIGANDS; N-HETEROCYCLIC CARBENES; PRIMARY AMINES; PROTONOLYSIS; TRIPLE BONDS;

CATALYSIS; COPPER; ETHERS; FUNCTIONAL GROUPS; O RINGS; REACTION KINETICS;

ACETYLENE;

EID: 84868551533     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs300544w     Document Type: Article

References (88)

1. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3159.
2. Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
3. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368-3398.
4. Brunet, J.-J.; Neibecker, D. Catalytic Hydroamination of Unsaturated Carbon-Carbon Bonds. In Catalytic Heterofunctionalization;, Togni, A., Grützmacher, H., Eds.; Wiley-VCH Verlag GmbH: Weinheim, FRG., 2001.
5. Tani, K.; Kataoka, Y. O-H Activation and Addition to Unsaturated Systems. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH Verlag GmbH: Weinheim, FRG, 2001; pp 171-216.
6. Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104-114.
7. Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
8. McDonald, F. E. Chem.-Eur. J. 1999, 5, 3103-3106.
9. Togni, A.; Grützmacher, H., Catalytic Heterofunctionalization: From Hydroamination to Hydrozirconation; Wiley-VCH: Weinheim, 2001.
10. Roundhill, D. M. Chem. Rev. 1992, 92, 1-27.
11. Ackermann, L.; Bergman, R. G.; Loy, R. N. J. Am. Chem. Soc. 2003, 125, 11956-11963.
12. Doye, S. Synlett 2004, 10, 1653-1672.
13. Li, C.; Thomson, R. K.; Gillon, B.; Patrick, B. O.; Schafer, L. L. Chem. Commun. 2003, 2462-2463.
14. Li, Y. W.; Fu, P. F.; Marks, T. J. Organometallics 1994, 13, 439- 440.
15. Li, Y. W.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295-9306.
16. Müller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A.-K.; Walter, E.; Yan, Y.-K. Organometallics 2000, 19, 170-183.
17. Müller, T. E.; Pleier, A. K. J. Chem. Soc., Dalton Trans. 1999, 583-587.
18. Kondo, T.; Okada, T.; Suzuki, T.; Mitsudo, T.-a. J. Organomet. Chem. 2001, 622, 149-154.
19. Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1999, 38, 3222-3225.
20. Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P. Organometallics 2005, 24, 4241-4250.
21. Compain, P.; Goré, J.; Vatéle, J.-M. Tetrahedron 1996, 52, 10405-10416.
22. Cacchi, S. J. Organomet. Chem. 1999, 576, 42-64.
23. Wakabayashi, Y.; Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. Tetrahedron 1985, 41, 3655-3661.
24. Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 121, 11680- 11683.
25. Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 2002, 124, 2528- 2533.
26. Kücükbay, H.; Cetinkaya, B.; Guesmi, S.; Dixneuf, P. H. Organometallics 1996, 15, 2434-2439.
27. Gabriele, B.; Salerno, G.; De Pascali, F.; Scianò, G. T.; Costa, M.; Chiusoli, G. P. Tetrahedron Lett. 1997, 38, 6877-6880.
28. Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687-7692.
29. Schabbert, S.; Schaumann, E. Eur. J. Org. Chem. 1998, 1873- 1878.
30. Seiller, B.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1994, 493-494.
31. Seiller, B.; Bruneau, C.; Dixneuf, P. H. Tetrahedron 1995, 51, 13089-13102.
32. Qing, F.-L.; Gao, W.-Z.; Ying, J. J. Org. Chem. 2000, 65, 2003- 2006.
33. Qing, F.-L.; Gao, W.-Z. Tetrahedron Lett. 2000, 41, 7727-7730.
34. Utimoto, K. Pure Appl. Chem. 1983, 55, 1845-1852.
35. Tzalis, D.; Koradin, C.; Knochel, P. Tetrahedron Lett. 1999, 40, 6193-6195.
36. McDonald, F. E.; Connolly, C. B.; Gleason, M. M.; Towne, T. B.; Treiber, K. D. J. Org. Chem. 1993, 58, 6952-6953.
37. Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 2003, 125, 7482- 7483.
38. McDonald, F. E.; Reddy, K. S.; Díaz, Y. J. Am. Chem. Soc. 2000, 122, 4304-4309.
39. McDonald, F. E.; Reddy, K. S. J. Organomet. Chem. 2001, 617- 618, 444-452.
40. Sheng, Y. H.; Musaev, D. G.; Reddy, K. S.; McDonald, F. E.; Morokuma, K. J. Am. Chem. Soc. 2002, 124, 4149-4157.
41. Wipf, P.; Graham, T. H. J. Org. Chem. 2003, 68, 8798-8807.
42. Hashmi, A. S. K.; Schäfer, S.; Wölfle, M.; Diez Gil, C.; Fischer, P.; Laguna, A.; Blanco, M. C.; Gimeno, M. C. Angew. Chem., Int. Ed. 2007, 46, 6184-6187.
43. Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem., Int. Ed. 2006, 45, 7896-7936.
44. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211.
45. Rudolph, M.; Hashmi, A. S. K. Chem. Commun. 2011, 47, 6536- 6544.
46. Ho, J. H. H.; Hodgson, R.; Wagler, J.; Messerle, B. A. Dalton Trans. 2010, 39, 4062-4069.
47. Genin, E.; Antoniotti, S.; Michelet, V.; Genêt, J.-P. Angew. Chem., Int. Ed. 2005, 44, 4949-4953.
48. Liu, B.; De Brabander, J. K. Org. Lett. 2006, 8, 4907-4910.
49. Diéguez-Vázquez, A.; Tzschucke, C. C.; Lam, W. Y.; Ley, S. V. Angew. Chem., Int. Ed. 2008, 47, 209-212.
50. Diéguez-Vázquez, A.; Tzschucke, C. C.; Crecente-Campo, J.; McGrath, S.; Ley, S. V. Eur. J. Org. Chem. 2009, 1698-1706.
51. Hashmi, A. S. K.; Bührle, M.; Wölfle, M.; Rudolph, M.; Wieteck, M.; Rominger, F.; Frey, W. Chem.-Eur. J. 2010, 16, 9846-9854.
52. Seo, S.; Marks, T. J. Chem.-Eur. J. 2010, 16, 5148-5162.
53. Pale, P.; Chuche, J. Eur. J. Org. Chem. 2000, 1019-1025.
54. Pale, P.; Chuche, J. Tetrahedron Lett. 1987, 28, 6447-6448.
55. Villemin, D.; Goussu, D. Heterocycles 1989, 29, 1255-1261.
56. Luo, F. T.; Schreuder, I.; Wang, R. T. J. Org. Chem. 1992, 57, 2213-2215.
57. Gabriele, B.; Salerno, G.; Fazio, A.; Pittelli, R. Tetrahedron 2003, 59, 6251-6259.
58. Riediker, M.; Schwartz, J. J. Am. Chem. Soc. 1982, 104, 5842- 5844.
59. Suzuki, M.; Yanagisawa, A.; Noyori, R. Tetrahedron Lett. 1983, 24, 1187-1188.
60. Yu, X. H.; Seo, S.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 7244-7245.
61. Seo, S. Y.; Yu, X. H.; Marks, T. J. J. Am. Chem. Soc. 2009, 131, 263-276.
62. Motta, A.; Fragalà, I. L.; Marks, T. J. Organometallics 2010, 29, 2004-2012.
63. Patil, N. T.; Raut, V. S.; Kavthe, R. D.; Reddy, V. V. N.; Raju, P. V. K. Tetrahedron Lett. 2009, 50, 6576-6579.
64. Praveen, C.; Iyyappan, C.; Perumal, P. T. Tetrahedron Lett. 2010, 51, 4767-4771.
65. Mankad, N. P.; Gray, T. G.; Laitar, D. S.; Sadighi, J. P. Organometallics 2004, 23, 1191-1193.
66. Laitar, D. S.; Tsui, E. Y.; Sadighi, J. P. J. Am. Chem. Soc. 2006, 128, 11036-11037.
67. Boogaerts, I. I. F.; Fortman, G. C.; Furst, M. R. L.; Cazin, C. S. J.; Nolan, S. P. Angew. Chem., Int. Ed. 2010, 49, 8674-8677.
68. Díez-González, S.; Escudero-Adán, E. C.; Benet-Buchholz, J.; Stevens, E. D.; Slawin, A. M. Z.; Nolan, S. P. Dalton Trans. 2010, 39, 7595-7606.
69. Fortman, G. C.; Slawin, A. M. Z.; Nolan, S. P. Organometallics 2010, 29, 3966-3972.
70. Munro-Leighton, C.; Blue, E. D.; Gunnoe, T. B. J. Am. Chem. Soc. 2006, 128, 1446-1447.
71. Delp, S. A.; Munro-Leighton, C.; Goj, L. A.; Ramirez, M. A.; Gunnoe, T. B.; Petersen, J. L.; Boyle, P. D. Inorg. Chem. 2007, 46, 2365-2367.
72. Munro-Leighton, C.; Delp, S. A.; Blue, E. D.; Gunnoe, T. B. Organometallics 2007, 26, 1483-1493.
73. Munro-Leighton, C.; Delp, S. A.; Alsop, N. M.; Blue, E. D.; Gunnoe, T. B. Chem. Commun. 2008, 111-113.
74. Messerle, B. A.; Vuong, K. Q. Organometallics 2007, 26, 3031- 3040.
75. Antoniotti, S.; Genin, E.; Michelet, V.; Genêt, J.-P. J. Am. Chem. Soc. 2005, 127, 9976-9977.
76. Fjermestad, T.; Ho, J. H. H.; Macgregor, S. A.; Messerle, B. A.; Tuna, D. Organometallics 2011, 30, 618-626 and references therein.
77. Goj, L. A.; Blue, E. D.; Delp, S. A.; Gunnoe, T. B.; Cundari, T. R.; Petersen, J. L. Organometallics 2006, 25, 4097-4104.
78. Bauschlicher, C. W.; Roos, B. O. J. Chem. Phys. 1989, 91, 4785- 4792.
79. Shoulders, B.; Welch, S. C. J. Chem. Educ. 1987, 64, 915-918.
80. Yu, T. B.; Bai, J. Z.; Guan, Z. B. Angew. Chem., Int. Ed. 2009, 48, 1097-1101.
81. Rozkiewicz, D. I.; Janczewski, D.; Verboom, W.; Ravoo, B. J.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2006, 45, 5292-5296.
82. Goj, L. A.; Blue, E. D.; Munro-Leighton, C.; Gunnoe, T. B.; Petersen, J. L. Inorg. Chem. 2005, 44, 8647-8649.
83. Hashmi, A. S. K.; Braun, I.; Rudolph, M.; Rominger, F. Organometallics 2012, 31, 644-661.
84. Hashmi, A. S. K.; Wieteck, M.; Braun, I.; Nösel, P.; Jongbloed, L.; Rudolph, M.; Rominger, F. Adv. Synth. Catal. 2012, 354, 555-562.
85. Hashmi, A. S. K.; Braun, I.; Nösel, P.; Schädlich, J.; Wieteck, M.; Rudolph, M.; Rominger, F. Angew. Chem., Int. Ed. 2012, 51, 4456- 4460.
86. Shannon, R. Acta Crystallogr., Sect. A 1976, 32, 751-767.
87. Langer, P.; Freifeld, I. Chem.-Eur. J. 2001, 7, 565-572.
88. Berg, T. C.; Gundersen, L. L.; Eriksen, A. B.; Malterud, K. E. Eur. J. Org. Chem. 2005, 4988-4994.