Cycloaddition-based formal C-H alkynylation of isoindoles leading to the synthesis of air-stable fluorescent 1,3-dialkynylisoindoles

Organic Letters

Volumn 15, Issue 14, 2013, Pages 3510-3513

  Ohmura, Toshimichi ^a   Kijima, Akihito ^a   Komori, Yusuke ^a   Suginome, Michinori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84880543551     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401051d     Document Type: Article

References (54)

1. Anthony, J. E. Chem. Rev. 2006, 106, 5028
2. Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452
3. Tour, J. M. Acc. Chem. Res. 2000, 33, 791
4. James, D. K.; Tour, J. M. Top. Curr. Chem. 2005, 257, 33
5. Bunz, U. H. F. Chem. Rev. 2000, 100, 1605
6. Matsumi, N.; Chujo, Y. Polym. J. 2008, 40, 77
7. Jones, G. B.; Chapman, B. J. In Comprehensive Heterocyclic Chemistry II; Katrizky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol 2, p 1.
8. Donohoe, T. J. In Science of Synthesis; Thomas, E. J., Vol. Ed.; Georg Thieme Verlag: Stuttgart, 2000; Vol 10, p 653.
9. Heugebaert, T. S. A.; Roman, B. I.; Stevens, C. V. Chem. Soc. Rev. 2012, 41, 5626
10. Zweig, A.; Metzler, G.; Maurer, A.; Roberts, B. G. J. Am. Chem. Soc. 1967, 89, 4091
11. Ding, Y.; Hay, A. S. J. Polm. Sci. Part A: Polym. Chem. 1999, 37, 3293
12. Gauvin, S.; Santerre, F.; Dodelet, J. P.; Ding, Y.; Hlil, A. R.; Hay, A. S.; Anderson, J.; Armstrong, N. R.; Gorjanc, T. C.; D'Iorio, M. Thin Solid Films 1999, 353, 218
13. Mi, B.-X.; Wang, P.-F.; Liu, M.-W.; Kwong, H.-L.; Wong, N.-B.; Lee, C.-S.; Lee, S.-T. Chem. Mater. 2003, 15, 3148
14. Jiao, L.; Yu, C.; Lin, M.; Wu, Y.; Cong, K.; Meng, T.; Wang, Y.; Hao, E. J. Org. Chem. 2010, 75, 6035
15. Diana, P.; Martorana, A.; Barraja, P.; Montalbano, A.; Carbone, A.; Cirrincione, G. Tetrahedron 2011, 67, 2072
16. Winn, M.; Zaugg, H. E. J. Org. Chem. 1969, 34, 249
17. Simons, S. S., Jr.; Ammon, H. L.; Doherty, R.; Johnson, D. F. J. Org. Chem. 1981, 46, 4739
18. Bonnett, R.; North, S. A.; Newton, R. F.; Scopes, D. I. C. Tetrahedron 1983, 39, 1401
19. Ohmura, T.; Kijima, A.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 6070
20. Ohmura, T.; Kijima, A.; Suginome, M. Org. Lett. 2011, 13, 1238
21. Dudnik, A. S.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2096
22. Messaoudi, S.; Brion, J.-D.; Alami, M. Eur. J. Org. Chem. 2010, 6495
23. Seregin, I., V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742
24. Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 4156
25. Gu, Y.; Wang, X. Tetrahedron Lett. 2009, 50, 763
26. Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem., Int. Ed. 2009, 48, 9346
27. Besselievre, F.; Piguel, S. Angew. Chem., Int. Ed. 2009, 48, 9553
28. de Haro, T.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 1512
29. Kim, S. H.; Chang, S. Org. Lett. 2010, 12, 1868
30. Yang, L.; Zhao, L.; Li, C.-J. Chem. Commun. 2010, 46, 4184
31. Brand, J. P.; Waser, J. Angew. Chem., Int. Ed. 2010, 49, 7304
32. Matsuyama, N.; Kitahara, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2358
33. Berciano, B. P.; Lebrequier, S.; Besselievre, F.; Piguel, S. Org. Lett. 2010, 12, 4038
34. Kim, S. H.; Yoon, J.; Chang, S. Org. Lett. 2011, 13, 1474
35. Brand, J. P.; Waser, J. Synthesis 2012, 44, 1155
36. Ackermann, L.; Kornhaass, C.; Zhu, Y. Org. Lett. 2012, 14, 1824
37. Shibahara, F.; Dohke, Y.; Murai, T. J. Org. Chem. 2012, 77, 5381
38. Brand, J. P.; Chevalley, C.; Scopelliti, R.; Waser, J. Chem.-Eur. J. 2012, 18, 5655
39. Tolnai, G. L.; Ganss, S.; Brand, J. P.; Waser, J. Org. Lett. 2013, 15, 112
40. Trofimov, B. A.; Stepanova, Z. V.; Sobenina, L. N.; Mikhaleva, A. I.; Ushakov, I. A. Tetrahedron Lett. 2004, 45, 6513
41. Trofimov, B. A.; Sobenina, L. N.; Stepanova, Z. V.; Vakul'skaya, T. I.; Kazheva, O. N.; Aleksandrov, G. G.; Dyachenko, O. A.; Mikhaleva, A. I. Tetrahedron 2008, 64, 5541 and references therein
42. LeHoullier, C. S.; Gribble, G. W. J. Org. Chem. 1983, 48, 2364
43. Chen, Z.; Müller, P.; Swager, T. M. Org. Lett. 2006, 8, 273
44. Chen, Y.-L.; Lee, M.-H.; Wong, W.-Y.; Lee, A. W. M. Synlett 2006, 2510
45. Duan, S.; Sinha-Mahapatra, D. K.; Herndon, J. W. Org. Lett. 2008, 10, 1541
46. Solé, D.; Serrano, O. Org. Biomol. Chem. 2009, 7, 3382
47. Tong, B. M. K.; Hui, B.W.-Q.; Chua, S. H.; Chiba, S. Synthesis 2011, 3552
48. For autooxidation of 1,3-diphenylisoindole, see: Ahmed, M.; Kricka, L. J.; Vernon, J. M. J. Chem. Soc., Perkin 1 1975, 71
49. Nakamura, S.; Kusuda, S.; Kawamura, K.; Toru, T. J. Org. Chem. 2002, 67, 640
50. Jacobi, P. A.; Tassa, C. Org. Lett. 2003, 5, 4879
51. Bornstein, J.; Remy, D. E. J. Chem. Soc. Chem. Commun. 1972, 1149
52. Kadzimirsz, D.; Hildebrandt, D.; Merz, K.; Dyker, G. Chem. Commun. 2006, 661
53. For desilylative Sonogashira coupling, see: Nishihara, Y.; Inoue, E.; Noyori, S.; Ogawa, D.; Okada, Y.; Iwasaki, M.; Takagi, K. Tetrahedron 2012, 68, 4869 and references therein
54. For the effect of trimethylsilylethynyl group on the fluorescence quantum yield of pyrene, see: Maeda, H.; Maeda, T.; Mizuno, K.; Fujimoto, K.; Shimizu, H.; Inoue, M. Chem.-Eur. J. 2006, 12, 824