Cobalt-catalyzed cross-coupling reaction of chloropyridines with grignard reagents

Chemistry Letters

Volumn 33, Issue 10, 2004, Pages 1240-1241

  Ohmiya, Hirohisa ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLMAGNESIUM CHLORIDE; COBALT; DIOXANE; MAGNESIUM DERIVATIVE; PYRIDINE DERIVATIVE; REAGENT; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; GRIGNARD REACTION;

EID: 11844277647     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.1240     Document Type: Article

References (22)

1. a) "Metal-catalyzed Cross-coupling Reactions," ed. by F. Diederich and P. J. Stang, Wiley-VCH, Weinheim (1998).
2. b) Special Issue: J. Organomet. Chem., ed. by K. Tamao, T. Hiyama, and E. Negishi, 653 (2002).
3. c) J. Tsuji, "Palladium Reagents and Catalysts. Innovations in Organic Synthesis," Wiley, Chichester (1996).
4. d) "Comprehensive Organic Synthesis," ed. by B. M. Trost, I. Fleming, and C. H. Heathcock, Pergamon Press, New York (1991), Vol. 3, Chap. 2.1-2.5.
5. e) "Cross-coupling Reactions. A Practical Guide," ed. by N. Miyaura, Springer, Berlin (2002).
6. a) K. Wakabayashi, H. Yorimitsu, and K. Oshima, J. Am. Chem. Soc., 123, 5374 (2001).
7. b) T. Tsuji, H. Yorimitsu, and K. Oshima, Angew. Chem., Int. Ed., 41, 4137 (2002).
8. c) K. Mizutani, H. Yorimitsu, and K. Oshima, Chem. Lett., 33, 832 (2004).
9. For other cobalt-catalyzed cross-coupling reactions: a) P. Gomes, C. Gosmini, and J. Périchon, J. Org. Chem., 68, 1142 (2003). b) G. Cahiez and H. Avedissian, Tetrahedron Lett., 39, 6159 (1998). c) H. Avedissian, L. Bérillon, G. Cahiez, and P. Knochel, Tetrahedron Lett., 39, 6163 (1998). d) Y. Nishii, K. Wakasugi, and Y. Tanabe, Synlett, 1998, 67. e) L. F. Wlsom, J. D. Hunt, and A. McKillop, Organomet. Chem. Rev., Sect. A, 8, 135 (1972). f) B. Sezen and D. Sames, Org. Lett., 5, 3607 (2003). g) M. S. Kharasch and E. K. Fields, J. Am. Chem. Soc., 63, 2316 (1941).
10. For other cobalt-catalyzed cross-coupling reactions: a) P. Gomes, C. Gosmini, and J. Périchon, J. Org. Chem., 68, 1142 (2003). b) G. Cahiez and H. Avedissian, Tetrahedron Lett., 39, 6159 (1998). c) H. Avedissian, L. Bérillon, G. Cahiez, and P. Knochel, Tetrahedron Lett., 39, 6163 (1998). d) Y. Nishii, K. Wakasugi, and Y. Tanabe, Synlett, 1998, 67. e) L. F. Wlsom, J. D. Hunt, and A. McKillop, Organomet. Chem. Rev., Sect. A, 8, 135 (1972). f) B. Sezen and D. Sames, Org. Lett., 5, 3607 (2003). g) M. S. Kharasch and E. K. Fields, J. Am. Chem. Soc., 63, 2316 (1941).
11. For other cobalt-catalyzed cross-coupling reactions: a) P. Gomes, C. Gosmini, and J. Périchon, J. Org. Chem., 68, 1142 (2003). b) G. Cahiez and H. Avedissian, Tetrahedron Lett., 39, 6159 (1998). c) H. Avedissian, L. Bérillon, G. Cahiez, and P. Knochel, Tetrahedron Lett., 39, 6163 (1998). d) Y. Nishii, K. Wakasugi, and Y. Tanabe, Synlett, 1998, 67. e) L. F. Wlsom, J. D. Hunt, and A. McKillop, Organomet. Chem. Rev., Sect. A, 8, 135 (1972). f) B. Sezen and D. Sames, Org. Lett., 5, 3607 (2003). g) M. S. Kharasch and E. K. Fields, J. Am. Chem. Soc., 63, 2316 (1941).
12. For other cobalt-catalyzed cross-coupling reactions: a) P. Gomes, C. Gosmini, and J. Périchon, J. Org. Chem., 68, 1142 (2003). b) G. Cahiez and H. Avedissian, Tetrahedron Lett., 39, 6159 (1998). c) H. Avedissian, L. Bérillon, G. Cahiez, and P. Knochel, Tetrahedron Lett., 39, 6163 (1998). d) Y. Nishii, K. Wakasugi, and Y. Tanabe, Synlett, 1998, 67. e) L. F. Wlsom, J. D. Hunt, and A. McKillop, Organomet. Chem. Rev., Sect. A, 8, 135 (1972). f) B. Sezen and D. Sames, Org. Lett., 5, 3607 (2003). g) M. S. Kharasch and E. K. Fields, J. Am. Chem. Soc., 63, 2316 (1941).
13. For other cobalt-catalyzed cross-coupling reactions: a) P. Gomes, C. Gosmini, and J. Périchon, J. Org. Chem., 68, 1142 (2003). b) G. Cahiez and H. Avedissian, Tetrahedron Lett., 39, 6159 (1998). c) H. Avedissian, L. Bérillon, G. Cahiez, and P. Knochel, Tetrahedron Lett., 39, 6163 (1998). d) Y. Nishii, K. Wakasugi, and Y. Tanabe, Synlett, 1998, 67. e) L. F. Wlsom, J. D. Hunt, and A. McKillop, Organomet. Chem. Rev., Sect. A, 8, 135 (1972). f) B. Sezen and D. Sames, Org. Lett., 5, 3607 (2003). g) M. S. Kharasch and E. K. Fields, J. Am. Chem. Soc., 63, 2316 (1941).
14. For other cobalt-catalyzed cross-coupling reactions: a) P. Gomes, C. Gosmini, and J. Périchon, J. Org. Chem., 68, 1142 (2003). b) G. Cahiez and H. Avedissian, Tetrahedron Lett., 39, 6159 (1998). c) H. Avedissian, L. Bérillon, G. Cahiez, and P. Knochel, Tetrahedron Lett., 39, 6163 (1998). d) Y. Nishii, K. Wakasugi, and Y. Tanabe, Synlett, 1998, 67. e) L. F. Wlsom, J. D. Hunt, and A. McKillop, Organomet. Chem. Rev., Sect. A, 8, 135 (1972). f) B. Sezen and D. Sames, Org. Lett., 5, 3607 (2003). g) M. S. Kharasch and E. K. Fields, J. Am. Chem. Soc., 63, 2316 (1941).
15. For other cobalt-catalyzed cross-coupling reactions: a) P. Gomes, C. Gosmini, and J. Périchon, J. Org. Chem., 68, 1142 (2003). b) G. Cahiez and H. Avedissian, Tetrahedron Lett., 39, 6159 (1998). c) H. Avedissian, L. Bérillon, G. Cahiez, and P. Knochel, Tetrahedron Lett., 39, 6163 (1998). d) Y. Nishii, K. Wakasugi, and Y. Tanabe, Synlett, 1998, 67. e) L. F. Wlsom, J. D. Hunt, and A. McKillop, Organomet. Chem. Rev., Sect. A, 8, 135 (1972). f) B. Sezen and D. Sames, Org. Lett., 5, 3607 (2003). g) M. S. Kharasch and E. K. Fields, J. Am. Chem. Soc., 63, 2316 (1941).
16. a) A. Fürstner and A. Leitner, Angew. Chem., Int. Ed., 41, 609 (2002).
17. b) A. Fürstner, A. Leitner, M. Méndez, and H. Krause, J. Am. Chem. Soc., 124, 13856 (2002).
18. Experimental Procedure: Anhydrous cobalt(II) acetylacetonate (25.7 mg, 0.10 mmol) was placed in a 20-mL two-necked flask. Anhydrous dioxane (3 mL) was then added under argon. After the solution became red, benzylmagnesium chloride (0.98 M ether solution, 3.1 mL, 3.0 mmol) was added at 0°C. The mixture was stirred for about 5 min at 25°C. 2-Chloropyridine (1, 114 mg, 1.0 mmol) was added dropwise to the reaction mixture. After being stirred for 30 min at 25°C, the reaction mixture was poured into water. The products were extracted with ethyl acetate (20 mL x 2). The combined organic layer was dried over sodium sulfate and concentrated. Purification of the crude product by silica gel column chromatography (20% ethyl acetate in hexane) provided the corresponding benzylated product 2 (137 mg, 0.81 mmol) in 81% yield.
19. The utility of benzylic pyridines is documented. For instance, a) M. E. Angiolelli, A. L. Casalnuovo, and T. P. Selby, Synlett, 2000, 905. b) W. Chai, A. Kwok, V. Wong, N. I. Carruthers, and J. Wu, Synlett, 2003, 2086. c) F. Speiser, P. Braunstein, and L. Saussine, Organometallics, 23, 2625 (2004).
20. The utility of benzylic pyridines is documented. For instance, a) M. E. Angiolelli, A. L. Casalnuovo, and T. P. Selby, Synlett, 2000, 905. b) W. Chai, A. Kwok, V. Wong, N. I. Carruthers, and J. Wu, Synlett, 2003, 2086. c) F. Speiser, P. Braunstein, and L. Saussine, Organometallics, 23, 2625 (2004).
21. The utility of benzylic pyridines is documented. For instance, a) M. E. Angiolelli, A. L. Casalnuovo, and T. P. Selby, Synlett, 2000, 905. b) W. Chai, A. Kwok, V. Wong, N. I. Carruthers, and J. Wu, Synlett, 2003, 2086. c) F. Speiser, P. Braunstein, and L. Saussine, Organometallics, 23, 2625 (2004).
22. T. Fujioka, T. Nakamura, H. Yorimitsu, and K. Oshima, Org. Lett., 4, 2257 (2002).