Nickel-catalyzed hydroheteroarylation of vinylarenes

Angewandte Chemie - International Edition

Volumn 49, Issue 26, 2010, Pages 4451-4454

  Nakao, Yoshiaki ^a   Kashihara, Natsuko ^a   Stephen Kanyiva, Kyalo ^a   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

C H activation; Carbene ligands; Heterocycles; Nickel; Vinylarenes

Indexed keywords

C-H ACTIVATION; CARBENE LIGANDS; CATALYST EFFECTS; ELECTRON WITHDRAWING GROUP; HETEROCYCLES; VINYLARENES;

ACTIVATION ANALYSIS; BIOACTIVITY; NICKEL; NICKEL ALLOYS; ORGANIC COMPOUNDS;

LIGANDS;

CARBENE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; METHANE; NICKEL; STYRENE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY;

CATALYSIS; HETEROCYCLIC COMPOUNDS; METHANE; NICKEL; STYRENE; VINYL COMPOUNDS;

EID: 77953682528     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201001470     Document Type: Article

References (26)

1. a) D. Lednicer, L. A. Mitscher, The Organic Chemistry of Drug Synthesis, Vol.1, Wiley, New York, 1977, Chapter 4;
2. b) D. Lednicer, L. A. Mitscher, The Organic Chemistry of Drug Synthesis Vol. 1, Wiley, New York, 1980, Chapter 2.
3. Y. Uchimaru, Chem. Commun. 1999, 1133.
4. a) S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature 1993, 366, 529;
5. b) F. Kakiuchi, S. Sekine, Y Tanaka, A. Kamatani, M. Sonoda, N. Chatani, S. Murai, Bull. Chem. Soc. Jpn. 1995, 68, 62;
6. c)T. Matsumoto, R. A. Periana, D. J. Taube, H. Yoshida, J. Mol. Catal. A 2002, 180, 1;
7. d) C.-H. Jun, C. W. Moon, X-B. Hong, S.-G. Lim, K.-Y. Chung, Y.-H. Kim, Chem. Eur. J. 2002, 8, 485;
8. e) R. Martinez, XP. Genet, S. Darses, Chem. Commun. 2008, 3855.
9. a) X Kischel, I. Jovel, K. Mertins, A. Zapf, M. Beller, Org. Lett. 2006, 8, 19;
10. b) H.-B. Sun, B. Li, R. M. Hua, Y. W. Yin, Eur. J. Org. Chem. 2006, 4231;
11. c) M. Rueping, B. X Nachtsheim, T. Scheidt, Org. Lett. 2006, 8, 3717;
12. d) Z. B. Zhang, X. Wang, R. A. Widenhoefer, Chem. Commun. 2006, 3717;
13. e) M.-Z. Wang, M.K. Wong, C.-M. Che, Chem. Eur. J. 2008, 14, 8353.
14. Y. Nakao, N. Kashihara, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc. 2008, 130, 16170.
15. K. S. Kanyiva, N. Kashihara, Y. Nakao, T. Hiyama, M. Ohashi, S. Ogoshi, unpublished results.
16. a) Y. Nakao, K. S. Kanyiva, S. Oda, T. Hiyama, J. Am. Chem. Soc. 2006, 128, 8146;
17. b) K.S. Kanyiva, Y. Nakao, T. Hiyama, Heterocycles 2007, 72, 677.
18. During the course of this study, Miura and co-workers reported addition of 1,3,4-oxadiazoles across vinylarenes by a nickel catalyst, see: T. Mukai, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 6410.
19. Y. Nakao, H. Idei, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc. 2009, 131, 15996.
20. V. P. W. Böhm, C. W K. Gstottmayr, T. Weskamp, W. A. Herrmann, Angew. Chem. 2001, 113, 3500;
21. Angew. Chem. Int. Ed. 2001, 40, 3387.
22. A. L. Casalnuovo, T. V. Rajanbabu, T. A. Ayers, T. H. Warren, J. Am. Chem. Soc. 1994, 116, 9869.
23. M. Shirakura, M. Suginome, Org. Lett. 2009, 11, 523.
24. a) Y. Nakao, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc. 2008, 130, 2448;
25. b) K. S. Kanyiva, F. Löbermann, Y Nakao, T. Hiyama, Tetrahedron Lett. 2009, 50, 3463.
26. Y Nakao, H. Idei, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc. 2009, 131, 5070.