Reactions of terminal polyynes with benzyl azide

Journal of Organic Chemistry

Volumn 75, Issue 24, 2010, Pages 8498-8507

  Luu, Thanh ^a   Medos, Boris J ^a   Graham, Erin R ^a   Vallee, Danielle M ^a   McDonald, Robert ^a   Ferguson, Michael J ^a   Tykwinski, Rik R ^b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ASCORBIC ACIDS; ETHYNYL; FUNCTIONALIZATIONS; GOOD YIELD; POLYYNES; STRUCTURAL CHARACTERISTICS; TERMINAL ALKYNE; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

ACETYLENE; KETONES; ORGANIC ACIDS;

FUNCTIONAL GROUPS;

1,2,3 TRIAZOLE DERIVATIVE; ALKYNE DERIVATIVE; ASCORBIC ACID; AZIDE; BENZYL DERIVATIVE; COPPER SULFATE; NATURAL PRODUCT;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 78650359621     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101870y     Document Type: Article

References (76)

1. Chalifoux, W. A.; Tykwinski, R. R. C. R. Chim. 2009, 12, 341-358
2. Witulski, B.; Schweikert, T.; Schollmeyer, D.; Nemkovich, N. A. Chem. Commun. 2010, 46, 2953-2955
3. Kivala, M.; Diederich, F. Acc. Chem. Res. 2009, 42, 235-248
4. Samoc, M.; Dalton, G. T.; Gladysz, J. A.; Zheng, Q.; Velkov, Y.; Agren, H.; Norman, P.; Humphrey, M. G. Inorg. Chem. 2008, 47, 9946-9957
5. Spitler, E. L.; Haley, M. M. Org. Biomol. Chem. 2008, 6, 1569-1576
6. Zheng, Q.; Bohling, J. C.; Peters, T. B.; Frisch, A. C.; Hampel, F.; Gladysz, J. A. Chem.-Eur. J. 2006, 12, 6486-6505
7. Eisler, S.; Slepkov, A. D.; Elliott, E.; Luu, T.; McDonald, R.; Hegmann, F. A.; Tykwinski, R. R. J. Am. Chem. Soc. 2005, 127, 2666-2676
8. Slepkov, A. D.; Hegmann, F. A.; Eisler, S.; Elliott, E.; Tykwinski, R. R. J. Chem. Phys. 2004, 120, 6807-6810
9. Ballmann, S.; Hieringer, W.; Secker, D.; Zheng, Q.; Gladysz, J. A.; Görling, A.; Weber, H. B. ChemPhysChem 2010, 11, 2256-2260
10. Wang, C.; Batsanov, A. S.; Bryce, M. R.; Martin, S.; Nichols, R. J.; Higgins, S. J.; Garcia-Suárez, V. M.; Lambert, C. J. J. Am. Chem. Soc. 2009, 131, 15647-15654
11. Long, N. J.; Williams, C. K. Angew. Chem., Int. Ed. 2003, 42, 2586-2617
12. Hisaki, I.; Shigemitsu, H.; Sakamoto, Y.; Hasegawa, Y.; Okajima, Y.; Nakano, K.; Tohnai, N.; Miyata, M. Angew. Chem., Int. Ed. 2009, 48, 5465-5469
13. Tahara, K.; Lei, S.; Mamdouh, W.; Yamaguchi, Y.; Ichikawa, T.; Uji-i, H.; Sonoda, M.; Hirose, K.; De Schryver, F. C.; De Feyter, S.; Tobe, Y. J. Am. Chem. Soc. 2008, 130, 6666-6667
14. Campbell, K.; Kuehl, C. J.; Ferguson, M. J.; Stang, P. J.; Tykwinski, R. R. J. Am. Chem. Soc. 2002, 124, 7266-7267
15. Nishinaga, T.; Nodera, N.; Miyata, Y.; Komatsu, K. J. Org. Chem. 2002, 67, 6091-6096
16. Carbon-Rich Compounds: Molecules to Materials; Haley, M. M.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2006.
17. Acetylene Chemistry: Chemistry, Biology, and Material Science; Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
18. Szafert, S.; Gladysz, J. A. Chem. Rev. 2006, 106, PR1-PR33
19. Szafert, S.; Gladysz, J. A. Chem. Rev. 2003, 103, 4175-4205
20. Pan, Y.; Lowary, T. L.; Tykwinski, R. R. Can. J. Chem. 2009, 87, 1565-1582
21. Shi Shun, A. L. K.; Tykwinski, R. R. Angew. Chem., Int. Ed. 2006, 45, 1034-1057
22. Bohlmann, F.; Burkhardt, H.; Zdero, C. Naturally Occurring Acetylenes; Academic Press: New York, 1973.
23. Li, Z.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2009, 131, 634-643
24. Xi, O.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2003, 125, 12400-12401
25. Wang, C.; Batsanov, A. S.; West, K.; Bryce, M. R. Org. Lett. 2008, 10, 3069-3072
26. West, K.; Wang, C.; Batsanov, A. S.; Bryce, M. R. Org. Biomol. Chem. 2008, 6, 1934-1937
27. West, K.; Hayward, L. N.; Batsanov, A. S.; Bryce, M. R. Eur. J. Org. Chem. 2008, 5093-5098
28. West, K.; Wang, C.; Batsanov, A. S.; Bryce, M. R. J. Org. Chem. 2006, 71, 8541-8544
29. Jones, E. R. H.; Stephenson, J. S. J. Chem. Soc. 1959, 2197-2203
30. For isolation, see: Kusumi, T.; Ohtani, I.; Nishiyama, K.; Kakisawa, H. Tetrahedron Lett. 1987, 28, 3981-3984 For the synthesis of 2a, see: Yamaguchi, M.; Park, H. J.; Hirama, M.; Torisu, K.; Nakamura, S.; Minami, T.; Nishihara, H.; Hiraoka, T. Bull. Chem. Soc. Jpn. 1994, 67, 1717-1725
31. Luu, T.; Tykwinski, R. R. J. Org. Chem. 2006, 71, 8982-8985
32. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; pp 1 - 176.
33. Tornøe, C. W.; Meldal, M. Peptides 2001, Proceedings of the American Peptide Symposium; Lebl, M.; Houghten, R. A., Eds.; American Peptide Society and Kluwer Academic Publishers: San Diego, CA, 2001; pp 263 - 264.
34. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
35. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
36. For selected reviews, see: Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302-1315
37. Amblard, F.; Cho, J. H.; Schinazi, R. F. Chem. Rev. 2009, 109, 4207-4220
38. Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952-3015
39. Meldal, M. Macromol. Rapid Commun. 2008, 29, 1016-1051
40. Johnson, J. A.; Finn, M. G.; Koberstein, J. T.; Turro, N. J. Macromol. Rapid Commun. 2008, 29, 1052-1072
41. Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Med. Res. Rev. 2008, 28, 278-308
42. Lutz, J.-F. Angew. Chem., Int. Ed. 2007, 46, 1018-1025
43. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249-1262
44. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51-68
45. Parts of this work have been communicated, see: Luu, T.; McDonald, R.; Tykwinski, R. R. Org. Lett. 2006, 8, 6035-6038
46. At the start of our work in this area (see ref 16), the reaction of terminal tri-, tetra-, or pentaynes with organic azides under Cu(I)/Cu(I) catalysis had not been explored, whereas one example existed for the reaction with a terminal diyne, see: Reck, F.; Zhou, F.; Girardot, M.; Kern, G.; Eyermann, C. J.; Hales, N. J.; Ramsay, R. R.; Gravestock, M. B. J. Med. Chem. 2005, 48, 499-506 Since this time, several reports have appeared, see: Aizpurua, J. M.; Azcune, I.; Fratila, R. M.; Balentova, E.; Sagartzazu-Aizpurua, M.; Miranda, J. I. Org. Lett. 2010, 12, 1584-1587
47. Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A.; Quarta, M. R.; Fittipaldi, M. Synthesis (Stuttgart) 2009, 3853-3859
48. Gauthier, S.; Weisbach, N.; Bhuvanesh, N.; Gladysz, J. A. Organometallics 2009, 28, 5597-5599
49. Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A.; Capuzzolo, F. Tetrahedron 2009, 65, 10573-10580
50. Reference 8c.
51. Monkowius, U.; Ritter, S.; König, B.; Zabel, M.; Yersin, H. Eur. J. Inorg. Chem. 2007, 4597-4606
52. The thermal reaction of azides with di- and triynes has been reported, see: Domnin, I. N.; Remizova, L. A.; Starova, G. L.; Rominger, F. Russ. J. Org. Chem. 2009, 45, 1678-1682
53. Bettison, R. M.; Hitchcock, P. B.; Walton, D. R. M. J. Organomet. Chem. 1988, 341, 247-254
54. Tikhonova, L. G.; Serebryakova, E. S.; Proidakov, A. G.; Sokolov, I. E.; Vereshchagin, L. I. J. Org. Chem. USSR 1981, 17, 645-648
55. Sokolyanskaya, L. V.; Volkov, A. N.; Trofimov, B. A. Khim. Geterotsikl. Soedin. 1979, 849 - 849; Chem. Heterocycl. Compd. 1979, 15, 689 - 689.
56. Dornow, A.; Rombush, R. Chem. Ber. 1958, 91, 1841-1851
57. It is important to note that during the concentration process, heat should not be applied and the solution should not be reduced to dryness since this could result in decomposition of the terminal alkyne.
58. The amount of benzyl azide was roughly based on the apparent success of the desilylation reaction, and varied from 0.66 to 1.0 equiv. Isolated yields are reported based on the amount of benzyl azide used; see the Experimental Section for details.
59. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313-3315
60. Bohlmann, F.; Arndt, C.; Bornowski, H.; Kleine, K.-M.; Herbst, P. Chem. Ber. 1964, 97, 1179-1192
61. Bohlmann, F.; Herbst., P.; Dohrmann, I. Chem. Ber. 1963, 96, 226-236
62. Hearn, M. T. W.; Jones, E. R. H.; Pellatt, M. G.; Thaller, V.; Turner, J. L. J. Chem. Soc., Perkin Trans. 1 1973, 2785-2788
63. Compound 7 has been previously prepared by another method, see ref 17f.
64. The successful thermal reaction of azides with propriolic acid has been reported: Alonso, G.; Garcia-Lopez, M. T.; Garcia-Munoz, G.; Madronero, R.; Rico, M. J. Heterocycl. Chem. 1970, 7, 1269-1272
65. Shi Shun, A. L. K.; Chernick, E. T.; Eisler, S.; Tykwinski, R. R. J. Org. Chem. 2003, 68, 1339-1347
66. Caution: It should be noted that Armitage has reported that the terminal triyne derived from 11d "exploded at 0 °C in the absence of air", see: Armitage, J. B.; Entwistle, N.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1954, 147-154 One should, therefore, not attempt to isolate this terminal triyne neat. Although we have not experienced any problems, the terminal polyynes reported herein should all be treated as potentially explosive and handled with care.
67. Bendz, G. Ark. Kemi 1959, 14, 305-321
68. Cambie, R. C.; Hirschberg, A.; Jones, E. R. H.; Lowe, G. J. Chem. Soc. 1963, 4120-4130
69. Bew, R. E.; Chapman, J. R.; Jones, E. R. H.; Lowe, B. E.; Lowe, G. J. Chem. Soc. C 1966, 129-135
70. Chalifoux, W. A.; Tykwinski, R. R. Nat. Chem. 2010, 2, 967-971.
71. See the Supporting Information for spectra of new compounds.
72. For the crystallographic characterization of other ethynyl-1,2,3-triazole derivatives, see refs 17c 18a 18b, and the following: Adamson, G. A.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1996, 1535-1543
73. The structures of 3c, 3g, and 10d have been communicated, see ref 16.
74. Liesbet Jongen, L.; Goderis, B.; Dolbnya, I.; Binnemans, K. Chem. Mater. 2003, 15, 212-217
75. Kendall, J.; McDonald, R.; Ferguson, M. J.; Tykwinski, R. R. Org. Lett. 2008, 10, 2163-2166
76. Eisler, S.; Chahal, N.; McDonald, R.; Tykwinski, R. R. Chem.-Eur. J. 2003, 9, 2542-2550