Nickel catalyzed cross-coupling of modified alkyl and alkenyl Grignard reagents with aryl- and heteroaryl nitriles: Activation of the C-CN bond

Tetrahedron Letters

Volumn 44, Issue 9, 2003, Pages 1907-1910

  Miller, Joseph A ^a   Dankwardt, John W ^a  

^a DSM Pharmaceutical Products   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; ALKENE DERIVATIVE; LITHIUM DERIVATIVE; NICKEL; NITRILE; REAGENT;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION;

EID: 0037463419     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00075-3     Document Type: Article

References (14)

1. For general references, see: (a) Negishi, E.-i.; Liu, F. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp. 1-48; (b) Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 3.4, pp. 161-240. (c) For a review on nickel catalyzed cross-coupling of Grignard reagents and aryl halides, see: Kumada, M. Pure Appl. Chem. 1980, 52, 669.
2. For general references, see: (a) Negishi, E.-i.; Liu, F. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp. 1-48; (b) Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 3.4, pp. 161-240. (c) For a review on nickel catalyzed cross-coupling of Grignard reagents and aryl halides, see: Kumada, M. Pure Appl. Chem. 1980, 52, 669.
3. For general references, see: (a) Negishi, E.-i.; Liu, F. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp. 1-48; (b) Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 3.4, pp. 161-240. (c) For a review on nickel catalyzed cross-coupling of Grignard reagents and aryl halides, see: Kumada, M. Pure Appl. Chem. 1980, 52, 669.
4. (a) For an example of C-F bond activation of aryl fluorides, see: Bohm, V. P. W.; Gstottmayer, C. W. K.; Weskamp, T.; Herrmann, W. A. Angew. Chem., Int. Ed. Engl. 2001, 40, 3387.
5. (b) For an example using a carbamate leaving group, see: Sengupta, S.; Leite, M.; Rasland, D. S.; Quesnelle, C.; Snieckus, V. J. Org. Chem. 1992, 57, 4066.
6. (c) For an example using a thioalkyl leaving group, see: Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Wenkert, E. Tetrahedron Lett. 1982, 23, 4629.
7. (a) Morvillo A., Turco A. J. Organomet. Chem. 208:1981;103.
8. (b) Abla M., Yamamoto T. J. Organomet. Chem. 532:1997;267.
9. (c) Garcia J.J., Brunkan N.M., Jones W.D. J. Am. Chem. Soc. 124:2002;9547.
10. Miller J.A. Tetrahedron Lett. 42:2001;6991.
11. 2 is now commercially available from Aldrich (catalog number 56,767-1).
12. 2 and 2-(dicyclohexylphosphino)-2′-methylbiphenyl (7.5 mol%) afforded small amounts of the desired styrene compound with the starting benzonitrile as the major component (1/9.8 3a/1a by GC).
13. Tamao K., Sumitani K., Kiso Y., Zembayashi M., Fujioka A., Kodama S.-i., Nakajima I., Minato A., Kumada M. Bull. Chem. Soc. Jpn. 49:1976;1958.
14. 2 (29 mg, 0.103 mmol) and tridecane (196 mg, 1.07 mmol) in THF (2 mL). The reaction was heated to 60°C for 15 h. An aliquot was withdrawn and quenched with 1 M solution of sodium citrate. GC analysis indicated the formation of 3c (1.21 mmol, 64%) and the cyclopropyl(4-methoxyphenyl)methanone (0.21 mmol).