A New Coupling Reaction of Alkyl Iodides with Electron Deficient Alkenes Nickel Boride (cat.) - Borohydride Exchange Resin in Methanol

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2357-2361

  Sim, Tae Bo ^a   Choi, Jaesung ^a   Joung, Meyoung Ju ^a   Yoon, Nung Min ^a  

^a Sogang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000918536     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961751f     Document Type: Article

References (15)

1. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
2. (b) Giese, B. Angew. Chem., Int. Ed. Engl. 1985, 24, 553.
3. (c) Neumann, W. P. Synthesis 1987, 665.
4. Curran, D. P. Radical Addition Reaction; Radical Cyclization and Sequential Radical Reaction. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 4, pp 715-831.
5. (a) Weinshenker, N. M.; Crosby, G. A.; Wong, J. Y. J. Org. Chem. 1975, 40, 1966.
6. (b) Leibner, J. E.; Jacobus, J. J. Org. Chem. 1979, 44, 449.
7. (c) Schumann, H.; Pachaly, B. Angew. Chem., Int. Ed. Engl. 1981, 20, 1043.
8. Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
9. Yoon, N. M.; Lee, H. J.; Ahn, J. H.; Choi, J. J. Org. Chem. 1994, 59, 4687.
10. A part of ester couplings has been communicated: Sim, T. B.; Choi, J.; Yoon, N. M. Tetrahedron Lett. 1996, 37, 3137.
11. Ethyl acrylate and acrylonitrile can be selectively hydrogenated in the presence of methyl crotonate and crotononitrile by nickel boride - BER in methanol at 0°C: Choi, J.; Yoon, N. M. Synthesis 1996, 597.
12. 1-Octene (20 mmol) was hydrogenated over nickel boride (1 mmol) on BER in 1 h; however, it was not hydrogenated in the presence of benzonitrile (5 mmol).
13. Cyclohexyl iodide was not reduced with BER in the absence of nickel boride.
14. Cekovic, J.; Saicic, R. S. Tetrahedron Lett. 1986, 27, 5893.
15. This BER could be directly used without drying. The same yields were obtained with dried BER.