Intramolecular arylcyanation of alkenes catalyzed by nickel/AlMe 2Cl

Journal of the American Chemical Society

Volumn 130, Issue 39, 2008, Pages 12874-12875

  Nakao, Yoshiaki ^a   Ebata, Shiro ^a   Yada, Akira ^a   Hiyama, Tamejiro ^a   Ikawa, Masashi ^b   Ogoshi, Sensuke ^b  

^a KYOTO UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC; CATALYST SYSTEM; CHEMICAL EQUATIONS; GOOD YIELD; NOVEL ACCESS; QUATERNARY CARBON; QUATERNARY STEREOCENTERS;

CHEMICAL REACTIONS; CYANIDES;

OLEFINS;

EID: 67650329691     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805088r     Document Type: Article

References (24)

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3. Nakao, Y.; Yada, A.; Ebata, S.; Hiyama, T. J. Am. Chem. Soc. 2007, 129, 2428.
4. For examples of catalytic and stoichiometric activation of C-CN bonds by nickel-Lewis acid, see: (a) Tolman, C. A.; Seidel, W. C.; Druliner, J. D.; Domaille, P. J. Organometallics 1984, 3, 33.
5. (b) Brunkan, N. M.; Brestensky, D. M.; Jones, W. D. J. Am. Chem. Soc. 2004, 126, 3627.
6. For the carbocyanation reaction of norbornene, see: (a) Nishihara, Y.; Inoue, Y.; Izawa, S.; Miyasaka, M.; Tanemura, K.; Nakajima, K.; Takagi, K. Tetrahedron 2006, 62, 9872.
7. (b) Nakao, Y.; Yada, A.; Satoh, J.; Ebata, S.; Oda, S.; Hiyama, T. Chem. Lett. 2006, 35, 790.
8. See Supporting Information for details.
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10. (b) Yasui, Y.; Kamisaki, H.; Takemoto, Y. Org. Lett. 2008, 10, 3303.
11. The relative stereochemistry of 2k was determined by X-ray crystallography.
12. PP = 24.0 Hz).
13. 2-acetonitrile nickel complex has been reported by Jones, see: Atesin, T. A.; Li, T.; Lachaize, S.; Brennessel, W. W.; Garcia, J. J.; Jones, W. D. J. Am. Chem. Soc. 2007, 129, 7562.
14. 3 as a ligand also gave 2a in a good yield.
15. 6): δ 13.5 (s).
16. PP = 27.3 Hz).
17. 2-ketone-nickel(0) complexes, see: Delbecq, F.; Sautet, P. J. Am. Chem. Soc. 1992, 114, 2446.
18. A full scope of the enantioselective arylcyanation will be reported in a forthcoming full paper.
19. Miyake, Y.; Nishibayashi, Y.; Uemura, S. Synlett 2008, 1747.
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