Fe(OTf)3-catalyzed addition of sp C-H bonds to olefins

Journal of the American Chemical Society

Volumn 131, Issue 8, 2009, Pages 2784-2785

  Kohno, Kazufumi ^a   Nakagawa, Kou ^b   Yahagi, Takeshi ^b   Choi, Jun Chul ^a   Yasuda, Hiroyuki ^a   Sakakura, Toshiyasu ^a,b  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CATALYST; C-C DOUBLE BONDS; C-H BOND; CATALYTIC ACTIVITY; ESTER FORMATION; HIGHER YIELD; METAL SALT; METAL-BASED CATALYSTS; NORBORNENES; OXIDATION-REDUCTION CYCLE; TRIFLATES; TRIFLIC ACIDS;

ACETYLENE; CARBOXYLIC ACIDS; ESTERS; LIGHTING; METALS; OLEFINS; ORGANIC ACIDS; PRECIOUS METALS; SCANDIUM; SILVER;

CATALYSTS;

ACETYLENE DERIVATIVE; ALKENE DERIVATIVE; CARBON; CARBOXYLIC ACID DERIVATIVE; CATION; COPPER DERIVATIVE; COPPER TRIFLUOROMETHANESULFONIC ACID; ESTER; FERRIC ION; FERRIC TRIFLUOROMETHANESULFONIC ACID; HYDROGEN; IRON DERIVATIVE; METAL; METAL SALT; NORBORNENE DERIVATIVE; SILVER DERIVATIVE; SILVER TRIFLUOROMETHANESULFONIC ACID; SODIUM CHLORIDE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ACID CATALYZED ADDITION; ACIDIFICATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; CROSS COUPLING REACTION; CYCLOADDITION; OXIDATION REDUCTION REACTION; PHASE TRANSITION;

EID: 77950860429     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja8090593     Document Type: Article

References (30)

1. For reviews, see: (a) Meijere, A. D.; Diederich, F. Metal- CatalyzedCrossCoupling Reactions; Wiley-VCH: New York, 2004.
2. (b) Yamamoto, H.; Ishihara, K. Acid Catalysis in Modern OrganicSynthesis; Wiley-VCH: New York, 2008.
3. For reviews, see: (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem.Rev. 2002, 102, 1731.
4. (b) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002,35, 826.
5. (a) Chen, L.; Li, C.-J. Chem. Commun. 2004 2362.
6. (b) Trost, B. M.; Kottirsch, G. J. Am. Chem. Soc. 1990,112, 2816.
7. (c) Rubin, M.; Markov, J.; Chuprakov, S.; Wink, D. J.; Gevorgyan, V.J. Org. Chem. 2003, 68, 6251.
8. (d) Bruyene, D.; Grigg, R.; Hinsley, J.; Hussain, R. K.; Korn, S.; De LaCierva, C. O.; Sridharan, V.; Wang, J. Tetrahedron Lett. 2003,44, 8669.
9. (e) Yin, J.; Chishom, J. D. Chem. Commun. 2006, 632.
10. (f) Tenaglia, A.; Giordano, L.; Buono, G. Org. Lett. 2006,8, 4315.
11. (a) For a review, see: Fujimori, S.; Knöpfel, T. F.; Zarotti, P.;Ichikawa, T.; Boyall, D.; Carreira, E. M. Bull. Chem. Soc. Jpn.2007, 80, 1635.
12. (b) Knöpfel, T. F.; Carreira, E. M. J. Am. Chem. Soc.2003, 125, 6054.
13. (c) Knöpfel, T. F.; Zarotti, P.; Ichikawa, T.; Carreira, E. M. J.Am. Chem. Soc. 2005, 127, 9682.
14. (d) Fujimori, S.; Carreira, E. M. Angew. Chem., Int. 2007,46, 4964.
15. (a) Nikishin, G. I.; Kovalev, I. P. Tetrahedron Lett. 1990,31, 7063.
16. (b) Lerum, R. V.; Chisholm, J. D. Tetrahedron Lett. 2004,45, 6591.
17. (c) Nishimura, T.; Guo, X.-X.; Uchiyama, N.; Katoh, T.; Hayashi, T. J.Am. Chem. Soc. 2008, 130, 1576.
18. (d) Yamaguchi, M.; Omata, K.; Hirama, M. Tetrahedron Lett.1994, 35, 5689.
19. (a) Picquet, M.; Bruneau, C; Dixneuf, P. H. Tetrahedron1999, 55, 3937.
20. (b) Chang, S.; Na, Y.; Choi, E.; Kim, S. Org. Lett. 2001,3, 2089.
21. (c) Nishimura, T.; Washitake, Y.; Uemura, S. Adv. Synth. Catal.2007, 349, 2563.
22. (d) Mitsudo, T.; Nakagawa, Y.; Watanabe, K.; Hori, Y.; Misawa, H.;Watanabe, H.; Watanabe, Y. J. Org. Chem. 1985, 50, 565.
23. (e) Mitsudo, T.; Hori, Y.; Watanabe, Y. Bull. Chem. Soc. Jpn.1986, 59, 3201.
24. Choi, J.-C.; Kohno, K.; Masuda, D.; Yasuda, H.; Sakakura, T. Chem.Commun. 2008, 777.
25. Knöpfel, T. F.; Boyall, D.; Carreira, E. M. Qrg. Lett.2004, 6, 2281.
26. Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118,4486.
27. Smith, B. M.; March, J. March's Advanced Organic Chemistry, 6thed.; Wiley-VCH: Hoboken, NJ, 2007; pp 646-648.
28. 3) anda hydrocarbon (norbornane) at 83°C. See: Gong, J.; Fuchs, P. L. J. Am.Chem. Soc. 1996, 118, 4486.
29. (b) The related acetylenes were also accessible through the Pd-catalyzeddecarboxylation of the corresponding propiolates. See: Rayabarapu, D. K.; Tunge,J. A. J. Am. Chem. Soc. 2005, 127, 13510.
30. Shirakura, M.; Suginome, M. J. Am. Chem. Soc. 2008, 130, 5410.