Nickel-catalyzed cycloadditions of thiophthalic anhydrideswith alkynes

Organic Letters

Volumn 13, Issue 8, 2011, Pages 1912-1915

  Inami, Tasuku ^a   Baba, Yoko ^a   Kurahashi, Takuya ^a   Matsubara, Seijiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79955397439     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200336c     Document Type: Article

References (19)

1. Kajita, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2008, 130, 17226.
2. Sulfur-containing heterocyclic compounds arewidely distributed in nature, and their biological and physiological effects are of interest. Pharmaceutical drugs, such as Raloxifene, Zileuton, Sertaconazole, Arzoxifene, Metizoline, and Sb-271046, contain benzothiophene structures.
3. Tseng, N.- W.; Lautens, M. J. Org. Chem. 2009, 74, 1809.
4. Benati, L.; Calestani, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Strazzari, S.; Zanardi, G. J. Org. Chem. 2003, 68, 3454.
5. Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905.
6. Nakamura, I.; Sato, T.; Yamamoto, Y. Ange W. Chem., Int. Ed. 2006, 45, 4473.
7. Leardini, R.; Franco Pedulli, G.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1985, 1390.
8. Trost, B. M.; Chen, F. Tetrahedron Lett. 1971, 12, 2603.
9. Sano, K.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1984, 57, 2741.
10. Yamamoto, T.; Sano, K.; Yamamoto, A. J. Am. Chem. Soc. 1987, 109, 1092.
11. Fischer, R.;Wlther, D.; Kempe, R.; Sieler, J.; Schönecker, B. J. Organomet. Chem. 1993, 447, 131.
12. Yoshino, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2009, 131, 7494.
13. Ooguri, A.; Nakai, K.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2009, 131, 13194.
14. For addition of the S-CO2R bond to alkynes, see: (a) Hua, R.; Takeda, H.; Onozawa, S.; Abe, Y.; Tanaka, M. J. Am. Chem. Soc. 2001, 123, 2899. For addition of the S-C(O)R bond to alkynes, see:
15. 2 bond to alkynes, see:
16. Toyofuku, M.; FujiWra, S.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2005, 127, 9706.
17. FujiWra, K.; Kurahashi, T.; Matsubara, S. Org. Lett. 2010, 12, 4548.
18. Terminal alkynes, such as 1-octyne and phenylacetylene, failed to participate in the reactions, presumably due to rapid oligomerization of alkynes.
19. For an example, see: Connor, D. T.; Cetenko, W. A.; Mullican, M. D.; Sorenson, R. J.; Unangst, P. C., Wikert, R. J.; Adolphson,R. L.; Kennedy, J. A.; Thueson, D. O. J. Med. Chem. 1992, 35, 958.