A domino process for benzyne preparation: Dual activation of o-(trimethylsilyl)phenols by nonafluorobutanesulfonyl fluoride

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1730-1733

  Ikawa, Takashi ^a   Nishiyama, Tsuyoshi ^a   Nosaki, Toshifumi ^a   Takagi, Akira ^a   Akai, Shuji ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BENZYNE; BUTANE; FLUORIDE; PHENOL DERIVATIVE; SULFONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION;

BENZENE DERIVATIVES; BUTANES; FLUORIDES; METHYLATION; MOLECULAR STRUCTURE; PHENOLS; SULFONES;

EID: 79953214980     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200252c     Document Type: Article

References (29)

1. For recent reviews, see: Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701-730
2. Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502-528
3. Dyke, A.; Hester, A.; Lloyd-Jones, G. Synthesis 2006, 4093-4112
4. Sanz, R. Org. Prep. Proced. Int. 2008, 40, 215-291
5. Yoshida, H.; Ohshita, J.; Kunai, A. Bull. Chem. Soc. Jpn. 2010, 83, 199-219
6. Kitamura, T.; Yamabe, M.; Inoue, K.; Todaka, M.; Fukatsu, N.; Meng, Z.; Fujiwara, Y. J. Am. Chem. Soc. 1999, 121, 11674-11679
7. Kitamura, T. Aust. J. Chem. 2010, 63, 987-1001
8. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211-1214
9. For recent examples, see: Gilmore, C. D.; Allan, K. M.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 1558-1559
10. Tadross, P. M.; Virgil, S. C.; Stoltz, B. M. Org. Lett. 2010, 12, 1612-1614
11. Morishita, T.; Yoshida, H.; Ohshita, J. Chem. Commun. 2010, 46, 640-642
12. Yoshida, H.; Okada, K.; Kawashima, S.; Tanino, K.; Ohshita, J. Chem. Commun. 2010, 46, 1763-1765
13. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302
14. 2, see: JP Pat., 119355, 2007.
15. Choy, P. Y.; Chow, W. K.; So, C. M.; Lau, C. P.; Kwong, F. Y. Chem.-Eur. J. 2010, 16, 9982-9985
16. NfF is less expensive than any of the common triflating reagents because it can be easily generated. For the synthesis of NfF, see: Zimmer, R.; Webel, M.; Reissig, H.-U. J. Prakt. Chem. 1998, 340, 274-277
17. Trifluoromethanesulfonyl fluoride (TfF) is another candidate of the dual activation reagent; however, it requires special care due to its low boiling point (-22 °C).
18. For a recent review, see: Högermeier, J.; Reissig, H.-U. Adv. Synth. Catal. 2009, 351, 2747-2763
19. The use of nonaflates 4 as benzyne precursors has never been reported.
20. For an example of the activation of CsF with 18-c-6 and MeCN, see: Nishikawa, T.; Shibuya, S.; Isobe, M. Synlett 1994, 482-484 For the complexation of CsF with 18-c-6, see: Takeda, Y.; Kawarabayashi, A.; Endo, K.; Yahata, T.; Kudo, Y.; Katsuta, S. Anal. Sci. 1998, 14, 215-223
21. Tadross, P. M.; Gilmore, C. D.; Bugga, P.; Virgil, S. C.; Stoltz, B. M. Org. Lett. 2010, 12, 1224-1227
22. The use of n BuLi as a base would be a solution; however, careful control of the reaction temperature at -100 °C was essential, and such harsh reaction conditions hamper their application to functionalized compounds; see: Peña, D.; Cobas, A.; Pérez, D.; Guitián, E. Synthesis 2002, 1454-1458
23. Akai, S.; Ikawa, T.; Takayanagi, S.; Morikawa, Y.; Mohri, S.; Tsubakiyama, M.; Egi, M.; Wada, Y.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 7673-7676
24. 2O and n BuLi predominantly gave the deacetalized products (2g′ and 3g′).
25. Shi, F.; Waldo, J. P.; Chen, Y.; Larock, R. C. Org. Lett. 2008, 10, 2409-2412
26. Liu, Z.; Larock, R. C. J. Org. Chem. 2006, 71, 3198-3209
27. 18-c-6 was added after the consumption of 3a.
28. Xie, C.; Liu, L.; Zhang, Y.; Xu, P. Org. Lett. 2008, 10, 2393-2396
29. Bříza, T.; Král, V.; Martásek, P.; Kaplánek, R. J. Fluorine Chem. 2008, 129, 235-247