Hidden Brønsted acid catalysis: Pathways of accidental or deliberate generation of triflic acid from metal triflates

Journal of Organic Chemistry

Volumn 76, Issue 22, 2011, Pages 9353-9361

  Dang, Tuan Thanh ^a   Boeck, Florian ^a   Hintermann, Lukas ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,2-DICHLOROETHANES; ACID CATALYSIS; ACID CATALYST; CATALYTIC SPECIES; CONTROL EXPERIMENTS; ELEVATED TEMPERATURE; HYDROALKOXYLATION; PRECATALYSTS; SYNTHETIC APPLICATION; TRIFLATES; TRIFLIC ACIDS;

RUTHENIUM COMPOUNDS; TOLUENE;

CHLORINE COMPOUNDS;

BRONSTED ACID; TOLUENE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; HYDROALKOXYLATION; SYNTHESIS; TEMPERATURE;

EID: 81055147777     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201631x     Document Type: Article

References (72)

1. Hintermann, L. Top. Organomet. Chem. 2010, 31, 123 and cited literature
2. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368
3. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079
4. Tani, K.; Kataoka, Y. In Catalytic Heterofunctionalization; Togni, A.; Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; p 171.
5. Hori, K.; Kitagawa, H.; Miyoshi, A.; Ohta, T.; Furukawa, I. Chem. Lett. 1998, 1083
6. Marotta, E.; Foresti, E.; Marcelli, T.; Peri, F.; Righi, P.; Scardovi, N.; Rosini, G. Org. Lett. 2002, 4, 4451
7. Loh, T.-P.; Hu, Q.-Y.; Ma, L.-T. J. Am. Chem. Soc. 2001, 123, 2450
8. Oe, Y.; Ohta, T.; Ito, Y. Chem. Commun. 2004, 1620
9. Oe, Y.; Ohta, T.; Ito, Y. Synlett 2005, 179
10. Ohta, T.; Kataoka, Y.; Miyoshi, A.; Oe, Y.; Furukawa, I.; Ito, Y. J. Organomet. Chem. 2007, 692, 671
11. Ito, Y.; Kato, R.; Hamashima, K.; Kataoka, Y.; Oe, Y.; Ohta, T.; Furukawa, I. J. Organomet. Chem. 2007, 692, 691
12. Oe, Y.; Ohta, T.; Ito, Y. Tetrahedron Lett. 2010, 51, 2806
13. Coulombel, L.; Favier, I.; Duñach, E. Chem. Commun. 2005, 2286
14. Lemechko, P.; Grau, F.; Antoniotti, S.; Duñach, E. Tetrahedron Lett. 2007, 48, 5731
15. Coulombel, L.; Rajzmann, M.; Pons, J. M.; Olivero, S.; Duñach, E. Chem.-Eur. J. 2006, 12, 6356
16. Kelly, B. D.; Allen, J. M.; Tundel, R. E.; Lambert, T. H. Org. Lett. 2009, 11, 1381
17. Taylor, J. G.; Whittall, N.; Hii, K. K. M. Chem. Commun. 2005, 5103
18. Chaminade, X.; Coulombel, L.; Olivero, S.; Duñach, E. Eur. J. Org. Chem. 2006, 3554
19. Yang, C. G.; He, C. J. Am. Chem. Soc. 2005, 127, 6966
20. Reich, N. W.; Yang, C.; Shi, Z.; He, C. Synlett 2006, 1278
21. Li, Z.; Zhang, J.; Brouwer, C.; Yang, C. G.; Reich, N. W.; He, C. Org. Lett. 2006, 8, 4175
22. Grant, V. H.; Liu, B. Tetrahedron Lett. 2005, 46, 1237
23. Yang, C. G.; Reich, N. W.; Shi, Z.; He, C. Org. Lett. 2005, 7, 4553
24. Qian, H.; Han, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 9536
25. Liu, C.; Bender, C. F.; Han, X.; Widenhoefer, R. A. Chem. Commun. 2007, 3607
26. Komeyama, K.; Morimoto, T.; Nakayama, Y.; Takaki, K. Tetrahedron Lett. 2007, 48, 3259
27. Choi, J. C.; Kohno, K.; Masuda, D.; Yasuda, H.; Sakakura, T. Chem. Commun. 2008, 777
28. Dzudza, A.; Marks, T. J. Org. Lett. 2009, 11, 1523
29. Dzudza, A.; Marks, T. J. Chem.-Eur. J. 2010, 16, 3403
30. Zhang, X.; Corma, A. Chem. Commun. 2007, 3080
31. Vece, V.; Ricci, J.; Poulain-Martini, S.; Nava, P.; Carissan, Y.; Humbel, S.; Duñach, E. Eur. J. Org. Chem. 2010, 6239
32. Adrio, L. A.; Quek, L. S.; Taylor, J. G.; Hii, K. K. M. Tetrahedron 2009, 65, 10334
33. Hirai, T.; Hamasaki, A.; Nakamura, A.; Tokunaga, M. Org. Lett. 2009, 11, 5510
34. Antoniotti, S.; Poulain-Martini, S.; Duñach, E. Synlett 2010, 2973
35. Wabnitz, T. C.; Yu, J. Q.; Spencer, J. B. Chem.-Eur. J. 2004, 10, 484
36. Coulombel, L.; Duñach, E. Green. Chem. 2004, 6, 499
37. Li, Z.; Zhang, J.; Brouwer, C.; Yang, C. G.; Reich, N. W.; He, C. Org. Lett. 2006, 8, 4175
38. Rosenfeld, D. C.; Shekhar, S.; Takemiya, A.; Utsunomiya, M.; Hartwig, J. F. Org. Lett. 2006, 8, 4179
39. Compare: Taylor, J. G.; Adrio, L. A.; Hii, K. M. Dalton Trans. 2010, 39, 1171
40. For additional studies addressing the question of metal versus acid catalysis, see: McKinney Brooner, R. E.; Widenhoefer, R. A. Chem.-Eur. J. 2011, 17, 6170
41. Tschan, M. J. L.; Thomas, C. M.; Strub, H.; Carpentier, J. F. Adv. Synth. Catal. 2009, 351, 2496
42. Bandini, M.; Eichholzer, A.; Kotrusz, P.; Tragni, M.; Troisi, S.; Umani-Ronchi, A. Adv. Synth. Catal. 2009, 351, 319
43. Youn, S. W.; Eom, J. I. J. Org. Chem. 2006, 71, 6705
44. Harrison, T. J.; Dake, G. R. Org. Lett. 2004, 6, 5023
45. Deng, C.-L.; Zou, T.; Wang, Z.-Q.; Song, R.-J.; Li, J.-H. J. Org. Chem. 2009, 74, 412
46. Arcadi, A.; Alfonsi, M.; Marinelli, F. J. Organomet. Chem. 2007, 692, 5322
47. Silver in Organic Chemistry; Harmata, M., Ed.; Wiley: New York, 2010.
48. Falzon, C. L.; Ackermann, U.; Spratt, N.; Tochon-Danguy, H. J.; White, J.; Howells, D.; Scott, A. M. J. Labelled Compds. Radiopharm. 2006, 49, 1089
49. 2-Chloroethyltriflate is described as sensitive to hydrolysis, fuming in air: Lown, J. W.; Joshua, A. V.; McLaughlin, L. W J. Med. Chem. 1980, 23, 798
50. Howells, R. D.; Mc Cown, J. D. Chem. Rev. 1977, 77, 69
51. Chapman, R. D.; Andreshak, J. L.; Herrlinger, S. P.; Shackelford, S. A.; Hildreth, R. A.; Smith, J. P. J. Org. Chem. 1986, 51, 3792
52. Chapman, R. D.; Andreshak, J. L.; Shackelford, S. A. J. Org. Chem. 1988, 53, 3771
53. Bonrath, W.; Haas, A.; Hoppmann, E.; Netscher, T.; Pauling, H.; Schager, F.; Wildermann, A. Adv. Synth. Catal. 2002, 344, 37
54. Youn, S. W. Synlett 2007, 3050
55. Adrio, L. A.; Hii, K. K. Chem. Commun. 2008, 2325
56. Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.; Rastelli, M.; Sartori, G. Synthesis 1998, 301
57. De Felice, V.; De Renzi, A.; Funicello, M.; Panunzi, A.; Saporito, A. Gazz. Chim. Ital. 1985, 115, 13
58. Jona, H.; Mandai, H.; Chavasiri, W.; Takeuchi, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2002, 75, 291
59. Kato, T.; Tanaka, M.; Hoshikawa, M.; Yagi, M. Tetrahedron Lett. 1998, 39, 7553
60. Claims regarding the use of in situ prepared t -BuOTf can be found in the literature, but this compound has only been characterized by NMR spectroscopy at -60 °C and decomposes above -30 °C with generation of polyisobutene: Hommeltoft, S. I.; Ekelund, O.; Zavilla, J. Ind. Eng. Chem. Res. 1997, 36, 3491
61. 2 is used to avoid confusion regarding stoichiometric ratios. Complex 7 is a dimer in the solid state: Kölle, U.; Kossakowski, J.; Klaff, N.; Wesemann, L.; Englert, U.; Heberich, G. E. Angew. Chem., Int. Ed. Engl. 1991, 30, 690
62. Masuda, K.; Ohkita, H.; Kurumatani, S.; Itoh, K. Organometallics 1993, 12, 2221
63. Fagan, P. J.; Ward, M. D.; Calabrese, J. C. J. Am. Chem. Soc. 1989, 111, 1698
64. Kaganovich, V. S.; Kudinov, A. R.; Rybinskaya, M. I. Russ. Chem. Bull. 1986, 35, 456
65. Kaganovich, V. S.; Kudinov, A. R.; Rybinskaya, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1986, 2, 492
66. Wheeler, D. E.; Hill, S. T.; Williams, J. D.; Wedyck, E. J. Inorg. Chim. Acta 1995, 231, 133
67. Suzuki, H.; Omori, H.; Lee, D. H.; Yoshida, Y.; Morooka, Y. Organometallics 1988, 7, 2243
68. Bardají, M.; Crespo, O.; Laguna, A.; Fischer, A. K. Inorg. Chim. Acta 2000, 304, 7
69. 6/BINAP system, see: Ohkouchi, M.; Masui, D.; Yamaguchi, M.; Yamagishi, T. J. Mol. Catal. A: Chem. 2001, 170, 1
70. Yamamoto, H.; Futatsugi, K. Angew. Chem., Int. Ed. 2005, 44, 1924
71. Speight, J. G. Lange's Handbook of Chemistry, 16 th ed.; McGraw-Hill: New York, 2005.
72. Lajunen, M.; Himottu, M. Acta Chem. Scand. 1989, 43, 957