Catalytic and computational studies of N-heterocyclic carbene or phosphine-containing copper(I) complexes for the synthesis of 5-iodo-1,2,3-triazoles

ACS Catalysis

Volumn 4, Issue 7, 2014, Pages 2274-2287

  Lal, Steven ^a   Rzepa, Henry S ^a   Díez González, Silvia ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

azide; click chemistry; copper; cycloaddition; iodotriazole

Indexed keywords

COPPER; CYCLOADDITION; ORGANIC COMPOUNDS; PHOSPHORUS COMPOUNDS;

1 ,3-DIPOLARCYCLOADDITION; AZIDE; CLICK CHEMISTRY; COMPUTATIONAL STUDIES; COPPER (I) COMPLEXES; IODOTRIAZOLE; MECHANISTIC PATHWAYS; N-HETEROCYCLIC CARBENES;

COPPER COMPOUNDS;

EID: 84903759030     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs500326e     Document Type: Article

References (94)

1. Huisgen, R. Pure Appl. Chem. 1989, 61, 613-628
2. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
3. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
4. Special issue on Click chemistry, Chem. Soc. Rev. 2010, 39, 1221-1408.
5. For a comprehensive review, see: Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952-3015
6. Click Chemistry for Biotechnology and Materials Science; Lahann, J., Ed.; Wiley: Chichester, U.K., 2009.
7. Berg, R.; Straub, B. F. Beilstein J. Org. Chem. 2013, 9, 2715-2750
8. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51-68
9. Díez-González, S.; Correa, A.; Cavallo, L.; Nolan, S. P. Chem.-Eur. J. 2006, 12, 7558-7564
10. Candelon, N.; Lastécouères, D.; Diallo, A. K.; Aranzaes, J. R.; Astruc, D.; Vincent, J. M. Chem. Commun. 2008, 741-743
11. Kuijpers, B. H. M.; Dijkmans, G. C. T.; Groothuys, S.; Quaedflieg, P. J. L. M.; Blaauw, R. H.; van Delft, F. L.; Rutjes, F. P. J. T. Synlett 2005, 3059-3062
12. Hein, J. E.; Tripp, J. C.; Krasnova, L. B.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2009, 48, 8018-8021
13. For one earlier copper-free (and non regioselective) example using ionic liquids as reaction medium. See: Zhong, P.; Guo, S.-R. Chin. J. Chem. 2004, 22, 1183-1186
14. García-álvarez, J.; Díez, J.; Gimeno, J. Green Chem. 2010, 12, 2127-2130
15. García-álvarez, J.; Díez, J.; Gimeno, J.; Suárez, F. J.; Vincent, C. Eur. J. Inorg. Chem. 2012, 5854-5863
16. Buckley, B. R.; Dann, S. E.; Heaney, H. Chem.-Eur. J. 2010, 16, 6278-6284
17. For a recent report on the iridium-mediated synthesis of 4-bromotriazoles, see: Rasolofonjatovo, E.; Theeramunkong, S.; Bouriaud, A.; Kolodych, S.; Chaumontet, M.; Taran, F. Org. Lett. 2013, 15, 4698-4701
18. For reactions carried out with a copper tubing/TTTA combination, see: Bogdan, A. R.; James, K. Org. Lett. 2011, 13, 4060-4063
19. Schwartz, E.; Breitenkamp, K.; Fokin, V. V. Macromolecules 2011, 44, 4735-4741
20. Juríček, M.; Stout, K.; Kouwer, P. H. J.; Rowan, A. E. J. Porphyrins Phthalocyanines 2011, 15, 905-907
21. Smith, P. A. S. Open-Chain Nitrogen Compounds, Vol. 2, Benjamin, New York, 1966, 211-246;.
22. Boyer, J. H.; Moriarty, R.; de Darwent, B.; Smith, P. A. S. Chem. Eng. News 1964, 42, 6
23. Rodionov, V. O.; Presolski, S. I.; Gardinier, S.; Lim, Y.-H.; Finn, M. G. J. Am. Chem. Soc. 2007, 129, 12696-12704
24. Rodionov, V. O.; Presolski, S. I.; Díaz Díaz, D.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc. 2007, 129, 12705-12712
25. For the elegant preparation of 5-iodotriazoles via the in situ electrophilic iodonisation of 5-H-triazoles, see: Brotherton, W. S.; Clark, R. J.; Zhu, L. J. Org. Chem. 2012, 77, 6443-6455
26. Díez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2008, 47, 8881-8884
27. 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
28. Lal, S.; Díez-González, S. J. Org. Chem. 2011, 76, 2367-2373
29. Lal, S.; McNally, J.; White, A. J. P.; Díez-González, S. Organometallics 2011, 30, 6225-6232
30. N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools (Ed: S. Díez-González), RSC, Cambridge, 2011.
31. Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612-3676
32. N-Heterocyclic Carbenes in Synthesis (Ed: Nolan, S. P.), Wiley-VCH, Weinheim, 2006.
33. Marion, N. NHC-Copper, Silver and Gold Complexes in Catalysis in N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools (Ed: S. Díez-González), RSC, Cambridge, 2011.
34. Díez-González, S.; Nolan, S. P. Aldrichimica Acta 2008, 41, 43-51
35. Gu, S.; Huang, J.; Liu, X.; Liu, H.; Zhou, Y.; Xu, W. Inorg. Chem. Commun. 2012, 21, 168-172
36. Lazreg, F.; Slawin, A. M. Z.; Cazin, C. S. J. Organometallics 2012, 31, 7969-7975
37. Hohloch, S.; Su, C.-Y.; Sarkar, B. Eur. J. Inorg. Chem. 2011, 3067-3075
38. Wang, W.; Wu, J.; Xia, C.; Li, F. Green Chem. 2011, 13, 3440-3445
39. Nakamura, T.; Terashima, T.; Ogata, K.; Fukuzawa, S.-i. Org. Lett. 2011, 13, 620-623
40. Clavier, H.; Nolan, S. P. Chem. Commun. 2010, 46, 841-861
41. Díez-González, S.; Scott, N. M.; Nolan, S. P. Organometallics 2006, 25, 2355-2358 See also reference 18a.
42. Teyssot, M.-L.; Chevry, A.; Traïkia, M.; El-Ghozzi, M.; Avignant, D.; Gautier, A. Chem.-Eur. J. 2009, 15, 6322-6326
43. Teyssot, M.-L.; Nauton, L.; Canet, J.-L.; Cisnetti, F.; Chevry, A.; Gautier, A. Eur. J. Org. Chem. 2010, 3507-3515
44. 1H NMR showed a mixture of starting material and a new compound which could be [CuCl(IPr)(phen)]. All attempts to separate both compounds failed. The lower conversion into a phen-adduct from [CuCl(IPr)] when compared to [CuCl(SIMes)] is probably due to the higher steric hindrance of the IPr ligand. For the synthesis of a related Cu-IPr complex, see: Krylova, V. A.; Djurovich, P. I.; Whited, M. T.; Thompson, M. Chem. Commun. 2010, 46, 6696-6698
45. [CuCl(IPr)] is available from Sigma-Aldrich, Strem and TCI. For its synthesis, see: Jurkauskas, V.; Sadighi, J. P.; Buchwald, S. L. Org. Lett. 2003, 5, 2417-2420
46. Campbell-Verduyn, L. S.; Mirfeizi, L.; Dierckx, R. A.; Elsinga, P. H.; Feringa, B. L. Chem. Commun. 2009, 2139-2141 See also reference 18d.
47. Pérez-Balderas, F.; Ortega-Muñoz, M.; Morales-Sanfrutos, J.; Hernández-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asin, J. A.; Isac-Garcia, J.; Santoyo-González, F. Org. Lett. 2003, 5, 1951-1954
48. Gonda, Z.; Novak, Z. Dalton. Trans 2010, 39, 726-729
49. Wang, D.; Li, N.; Zhao, M.; Shi, W.; Ma, C.; Chen, B. Green Chem. 2010, 12, 2120-2123
50. Wang, D.; Zhao, M.; Liu, X.; Chen, Y.; Li, N.; Chen, B. Org. Biomol. Chem. 2012, 10, 229-231
51. Li, L.; Lopes, P. S.; Rosa, V.; Figueira, C. A.; Lemos, M. A. N. D. A.; Duarte, M. T.; Avilés, T.; Gomes, P. T. Dalton Trans. 2012, 41, 5144-5154
52. Apputkkuttan, P.; Dehaen, W.; Fokin, V. V.; Van der Eycken, E. Org. Lett. 2004, 6, 4223-4225
53. For a single example with a phosphite ligand, see: Nishizawa, Y. Bull. Chem. Soc. Jpn. 1961, 34, 1170-1178
54. Scuster, I. I.; Roberts, J. D. J. Org. Chem. 1979, 44, 2658-2662
55. Fife, D. J.; Moore, W. M.; Morse, K. W. Inorg. Chem. 1984, 23, 1684-1691
56. Buckley, B. R.; Dann, S. E.; Heaney, H.; Stubbs, E. C. Eur. J. Org. Chem. 2011, 770-776
57. Cai, C.; Vasella, A. Helv. Chim. Acta 1995, 78, 2053-2064
58. Alami, M.; Ferri, F. Tetrahedron Lett. 1996, 37, 2763-2766
59. Chai, J.-D.; Head-Gordon, M. Phys. Chem. Chem. Phys. 2008, 10, 6615-6620
60. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297-3305
61. Downing, J.; Murray-Rust, P.; Tonge, A. P.; Morgan, P.; Rzepa, H. S.; Cotterill, F.; Day, N.; Harvey, M. J. J. Chem. Inf. Mod. 2008, 48, 1571-1581
62. Scalmani, G.; Frisch, M. J. J. Chem. Phys. 2010, 132, 114110
63. York, D. M.; Karplus, M. J. Phys. Chem. A 1999, 103, 11060-11079
64. Carlqvist, P.; Eklund, R.; Brinck, T. J. Org. Chem. 2001, 66, 1193-1199
65. Alvarez-Idaboy, J. R.; Reyes, L.; Cruz, J. Org. Lett. 2006, 8, 1763-1765
66. Lebel, H.; Janes, M. K.; Charette, A. B.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5046-5047
67. Rasappan, R.; Hager, M.; Gissibi, A.; Reiser, O. Org. Lett. 2006, 8, 6099-6102
68. Wang, D.; Cai, R.; Sharma, S.; Jirak, J.; Thummanapelli, S. K.; Akhmedov, N. G.; Zhang, H.; Liu, X.; Petersen, J. L.; Shi, X. J. Am. Chem. Soc. 2012, 134, 9012-9019 See also reference 18b.
69. Díez-González, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874-883
70. Muetterties, E. L.; Alegranti, C. W. J. Am. Chem. Soc. 1970, 92, 4114-4115
71. Lippard, S. J.; Mayerle, J. J. Inorg. Chem. 1972, 11, 753-759
72. Fife, D. J.; Moore, W. M.; Morse, K. W. Inorg. Chem. 1984, 23, 1684-1691
73. Reddy and co-workers reported the only ligandless catalytic system for this reaction: Reddy, K. R.; Venkateshwar, M.; Maheswari, C. U.; Kumar, P. S. Tetrahedron Lett. 2010, 51, 2170-2173 However, when we applied their reaction conditions (5 mol % CuI in DMSO at 80°C for 18 h) to our model reaction, only 8% conversion into triazole 1a was obtained.
74. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635-646
75. Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406
76. Cristau, H. J.; Chiche, L.; Kadoura, J.; Torreilles, E. Tetrahedron Lett. 1988, 29, 3931-3934
77. de la Fuente, G. F.; Huheey, J. E. Phosphorus, Sulfur, and Silicon 1993, 78, 23-36
78. Molina, P.; López-Leonardo, C.; Llamas-Botía, J.; Foces-Foces, C.; Fernández-Castaño, C. Tetrahedron 1996, 52, 9629-9642
79. Elson, K. E.; Jenkins, I. D.; Loughlin, W. A. Aust. J. Chem. 2004, 57, 371-376
80. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210-216
81. Straub, B. F. Chem. Commun. 2007, 3868-3870
82. Ahlquist, M.; Fokin, V. V. Organometallics 2007, 26, 4389-4391
83. Zhou, Y.; Lecourt, T.; Micouin, L. Angew. Chem., Int. Ed. 2010, 49, 2607-2610
84. Nolte, C.; Mayer, P.; Straub, B. F. Angew. Chem., Int. Ed. 2007, 46, 2101-2103
85. For a recent report on a notable exception, see: Winn, J.; Pinczewska, A.; Goldup, S. M. J. Am. Chem. Soc. 2013, 135, 13318-13321
86. Cantillo, D.; ávalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Org. Biomol. Chem. 2011, 9, 2952-2958
87. Cremer, D.; Krafka, E. Acc. Chem. Res. 2010, 43, 591-601
88. Cadiot, P.; Chodkiewicz, W. in Chemistry of Acetylenes, Viehe, H. G., ed, Marcel Dekker, New York, 1969; p 597.
89. Chodkiewicz, W. Ann. Chim. Paris 1957, 2, 819-869
90. Alami, M.; Ferri, F. Tetrahedron Lett. 1996, 37, 2763-2766
91. Hosho, M.; Okimoto, M.; Nakamura, S.; Takahashi, S. Synthesis 2011, 3839-3847
92. Worrell, B. T.; Malik, J. A.; Fokin, V. V. Science 2013, 340, 457-460
93. Johnson, E. R.; Keinan, S.; Mori-Sánchez, P.; Contreras- García, J.; Cohen, A. J.; Yang, W. J. Am. Chem. Soc. 2010, 132, 6498-6506
94. Armstrong, A.; Boto, R. A.; Dingwall, P.; Contreras-García, J.; Harvey, M. J.; Mason, N.; Rzepa, H. S. Chem. Sci. 2014, 5, 2057-2071