The triazolyl analogue of the trityl cation

Tetrahedron Letters

Volumn 54, Issue 33, 2013, Pages 4362-4364

  Oukessou, Mohamed ^a,b   Génisson, Yves ^a   El Arfaoui, Dounia ^a,b   Ben Tama, Abdeslem ^b   El Hadrami, El Mestafa ^b   Chauvin, Remi ^a,c,d  

^a Université Paul Sabatier Toulouse III   (France)

^b SIDI MOHAMED BEN ABDELLAH UNIVERSITY   (Morocco)

^c LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

^d Université Paul Sabatier   (France)

Author keywords

Carbenium; Tris(1,2,3 triazolyl)methanol; Tris(triazolyl) methylium; Trityl cation

Indexed keywords

AZIDE; BENZYL AZIDE; CATION; COPPER; METHANOL; NUCLEOPHILE; TRIAZOLYLMETHANE; TRIETHYNYLMETHANOL; TRIFUOROACETIC ANHYDRIDE; TRIS(3 BENZYL TRIAZOL 5 YL)CARBENIUM; TRIS(3 BENZYL TRIAZOL 5 YL)METHANOL; TRITYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS;

EID: 84880039958     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.05.138     Document Type: Article

References (63)

1. M. Gomberg J. Am. Chem. Soc. 22 1900 757 771
2. W.B. Renfrow Jr., and C.R. Hauser Org. Synth. 2 1943 607
3. The first indirect mention with perchlorometallate anions (ZnCl 3 -, HgCl 3 -, FeCl 4 -) is due to Gomberg: M. Gomberg J. Am. Chem. Soc. 23 1901 496 502
4. I.I. Schuster, A.K. Colter, and R.J. Kurland J. Am. Chem. Soc. 90 1968 4679 4687
5. G.A. Olah, J.J. Svoboda, and J.A. Olah Synthesis 1972 544
6. C.J. Urch Triphenylmethyl Hexafluorophosphate Encyclopedia of Reagents for Organic Synthesis 2001 Wiley
7. H.J. Dauben Jr., L.R. Honnen, and K.M. Harmon J. Org. Chem. 25 1960 1442 1445
8. H. Liang Synlett 2010 333 334 and references therein
9. F.L. Dickert, K.D. Fritsch, G.R. Bauer, and G. Mages Zeitschrift für Physikalische Chemie 159 1988 1 10
10. S. Minegishi, and H. Mayr J. Am. Chem. Soc. 125 2003 286 295
11. M. Horn, and H. Mayr Eur. J. Org. Chem. 2011 6470 6475
12. (c) Mayr's Database of Reactivity Parameters: http://www.cup.lmu.de/oc/ mayr/reaktionsdatenbank/fe/showclass/65.
13. P. Huszthy, K. Lempert, and G. Simig J. Chem. Soc., Perkin. Trans. 2 1985 1351 1354
14. T. Mukaiyatna, H. Akamatsu, and J.S. Han Chem. Lett. 1990 889 892
15. S.E. Denmark, and C.-T. Chen Tetrahedron Lett. 35 1994 4327 4330
16. M. Wada, T. Watanabe, S. Natsume, H. Mishima, K. Kirishima, and T. Erabi Bull. Chem. Soc. Jpn. 68 1995 3233 3240
17. M.H. Acar, Y. Yagci, and W. Schnabel Polym. Int. 46 1998 331 335
18. See for examples: C.T. Chen, S.-D. Chao, K.C. Yen, C.-H. Chen, I.-C. Chou, and S.W. Hon J. Am. Chem. Soc. 119 1997 11341 11342C
19. T. Chen, and S.-D. Chao J. Org. Chem. 64 1999 1090 1091
20. For a recent review, see: M. Horn, and H. Mayr J. Phys. Org. Chem. 25 2012 979 988
21. K. Komatsu, T. Takai, S. Aonuma, and K. Takeuchi Tetrahedron Lett. 29 1988 5157 5160
22. M.C. Lopez, I. Demirtas, H. Maskill, and M. Mishima J. Phys. Org. Chem. 21 2008 614 621
23. T. Gessner, and U. Mayer Triarylmethane and Diarylmethane Dyes Ullmann's Encyclopedia of Industrial Chemistry 2000 Wiley
24. G.A. Olah, Q. Liao, J. Casanova, R. Bau, G. Rasul, and G.K.S. Prakash J. Chem. Soc., Perkin Trans. 2 1998 2239 2242
25. N. Morita, and T. Asao Tetrahedron Lett. 32 1991 773 776
26. S.-I. Naya, and M. Nitta Tetrahedron 59 2003 4157 4165
27. F. Taddei, P. Spagnolo, and M. Tiecco Org. Magn. Reson. 2 1970 159 164
28. A. Ishii, J. Nakayama, Y. Endo, and M. Hoshino Tetrahedron Lett. 31 1990 2623 2626
29. B. Abarca, G. Asensio, R. Ballesteros, and T. Varea J. Org. Chem. 56 1991 3224 3229
30. J. Fabian, H. Hartmann, and A. Noack J. Phys. Org. Chem. 16 2003 53 62
31. C. De Diego, C. Avendano, and J. Elguero Chem. Scr. 28 1988 403 409
32. V. Nair, S. Thomas, S.C. Mathew, and K.G. Abhilash Tetrahedron 62 2006 6731 6747
33. K. Matsumoto, M. Kannami, and M. Oda Tetrahedron Lett. 44 2003 2861 2864
34. R. Huisgen Proc. Chem. Soc. 1961 357 396
35. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004 2021
36. M. Meldal, and C.W. Tornoe Chem. Rev. 108 2008 2952 3015
37. J. McNulty, and K. Keskar Eur. J. Org. Chem. 2012 5462 5470
38. A. Mrozek, J. Karolak-Wojciechowska, P. Amiel, and J. Barbe J. Mol. Struct. 524 2000 151 157
39. A.T. Balaban, D.C. Oniciu, and A.R. Katritzky Chem. Rev. 104 2004 2777 2812
40. J. Aihara Bull. Chem. Soc. Jpn. 81 2008 241 247
41. R. Chauvin, C. Lepetit, P.W. Fowler, and J.-P. Malrieu Phys. Chem. Chem. Phys. 2010 5295 5306
42. H. Hauptmann Tetrahedron Lett. 40 1974 3587 3588
43. H. Hauptmann Tetrahedron 32 1976 1293 1997
44. A.H. Alberts, and H. Wynberg J. Chem. Soc., Chem. Commun. 1988 748 749
45. N.P. Bowling, and R.J. McMahon J. Org. Chem. 71 2006 5841 5847
46. S. Özcubukcu, E. Ozkal, C. Jimeno, and M.A. Pericas Org. Lett. 11 2009 4680 4683
47. E. Ozkal, S. Özçubukçu, C. Jimeno, and M.A. Pericas Catal. Sci. Technol. 2 2012 195 200
48. S.K. Chaudhary, and O. Hernandez Tetrahedron Lett. 20 1979 95 98
49. Y. Kobayashi, Y. Kitano, and F. Sato J. Chem. Soc., Chem. Commun. 1984 1329 1330
50. M. Maltese, M.C. Vergari, and M. Pia Donzello Tetrahedron Lett. 52 2011 483 487
51. W.E. Bachmann Org. Synth. 3 1955 841 842 Coll. Vol.
52. J. Busch-Petersen, and E.J. Corey Tetrahedron Lett. 41 2000 2515 2518
53. P. Huszthy, G. Lzso, K. Lempert, M. Gyor, and A. Rockenbauer J. Chem. Soc. Perkin. Trans. 2 1990 2009 2015
54. S.Z. Zard Xanthates and Related Derivatives as Radical Precursors Encyclopedia of Radicals in Chemistry, Biology and Materials 2012 Wiley
55. Y. Sato, T. Aoyama, T. Takido, and M. Kodomari Tetrahedron 68 2012 7077 7081
56. R. Suzuki, H. Tsukuda, N. Watanabe, Y. Kuwatani, and I. Ueda Tetrahedron 54 1998 2477
57. L. Maurette, C. Tedeschi, E. Sermot, M. Soleilhavoup, F. Hussain, B. Donnadieu, and R. Chauvin Tetrahedron 60 2004 10077 10098
58. R.E. Oyler, B.E. Ketz, and T.E. Glass Tetrahedron Lett. 41 2000 8247 8250
59. O.B. Ryan, K.-T. Smith, and M. Tilset J. Organomet. Chem. 421 1991 315 322
60. C.A. MacKenzie, and G. Chuchani J. Org. Chem. 20 1955 336 345
61. J. Zeidler, and B. Golankiewicz Tetrahedron 54 1998 2941 2952
62. G.W. Kabalka, M.-L. Yao, S. Borella, and L.K. Goins Organometallics 26 2007 4112 4114
63. See for example: F. Wang, J.A.D. Good, O. Rath, H.Y. Kristal Kaan, O.B. Sutcliffe, S.P. Mackay, and F. Kozielski J. Med. Chem. 55 2012 1511 1525