Ruthenium-catalyzed arylation of 2-alkenylpyridines with aryl bromides: Alternative E,Z-selectivity to Mizoroki-Heck reaction

Organic Letters

Volumn 7, Issue 18, 2005, Pages 4009-4011

  Oi, Shuichi ^a   Sakai, Kaori ^a   Inoue, Yoshio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 24944442184     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051654l     Document Type: Article

References (18)

1. (a) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
2. (b) Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320.
3. For reviews, see: (a) Heck, R. F. Org. React. 1982, 27, 345.
4. (b) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 4.
5. (c) Tsuji, J. Palladium Reagents and Catalysts; InnoVations in Organic Synthesis; Wiley: Chichester, 1996.
6. (a) Oi, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y. Org. Lett. 2001, 3, 2579.
7. (b) Oi, S.; Ogino, Y.; Fukita, S.; Inoue, Y. Org. Lett. 2002, 4, 1783.
8. (c) Oi, S.; Aizawa, E.; Ogino, Y.; Inoue, Y. J. Org. Chem. 2005, 70, 3113.
9. Ruthenium catalyzed Mizoroki-Heck-type olefination and related reactions: (a) Na, Y.; Park, S.; Han, S.; Han, H.; Ko, S.; Chang, S. J. Am. Chem. Soc. 2004, 126, 250.
10. (b) Chatterjee, A. K.; Toste, F. D.; Choi, T.; Grubbs, R. H. Adv. Synth. Catal. 2002, 344, 634.
11. Although the selectivity is not high, Z-selective Mizoroki-Heck reaction catalyzed by palladium has been reported. (a) Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2001, 123, 8217.
12. (b) Svennebring, A.; Nilsson, P.; Larhed, M. J. Org. Chem. 2004, 69, 3345.
13. 4. After the solvent was removed in vacuo, the residue was purified by silica gel flash chromatography (hexanes-EtOAc, 5:1) to give (Z)-3aa (77.1 mg, 0.395 mmol). All other reactions were performed using the same procedure.
14. Heteroatom directed cyclometalation, see: Omae, I. Coord. Chem. Rev. 2004, 248, 995.
15. Review: Kakiuchi, F.; Murai, S. In Topics in Organometallic Chemistry; Murai, S., Ed.; Springer: Berlin, 1999; Vol. 3, pp 47-79.
16. (a) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129.
17. (b) Trost, B. M.; Imi, K.; Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
18. (c) Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1998, 699.