Nickel-Catalyzed Michael Additions of β-Dicarbonyls

Journal of Organic Chemistry

Volumn 45, Issue 7, 1980, Pages 1246-1249

  Nelson, John H ^a   Howells, Peter N ^a   DeLullo, George C ^a   Landen, George L ^a   Henry, Ronald A ^b  

^a UNIVERSITY OF NEVADA   (United States)

^b NAVAL SURFACE WARFARE CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847086686     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo01295a017     Document Type: Article

References (10)

1. For a comprehensive review of the Michael reaction see: Bergman, E. D.; Ginsberg, D.; Rappo, R. Org. React. 1959, 10, 179.
2. Krychtal, G. V.; Kulganek, V. V.; Kucherov, V. F.; Yanovskaya, L. A. Synthesis 1979, 107.
3. See, e.g.: Ugo, R., Ed. “Aspects of Homogeneous Catalysis”; D. Reidel Publishing Co.: Holland, 1974; Vol. 2. Synthesis., 1977, Vol. 3. He-gedus, L. S. J. Organomet. Chem. 1977, 126, 151. Synthesis. 1975, 103, 421. Seyferth, D., Ed. “New Applications of Organometallic Reagents in Organic Synthesis”; Elsevier: New York, 1976.
4. Eckberg, R. P.; Henry, R. A.; Cary, L. W.; Nelson, J. H. Inorg. Chem. 1977, 16, 2977. Kenney, J. W.; Nelson, J. H.; Henry, R. A. J. Chem. Soc., Chem. Commun. 1973, 690. Howells, P. N.; Kenney, J. W.; Nelson, J. H.; Henry, R. A. Inorg. Chem., 1976,15, 124. Eckberg, R. P.; Nelson, J. H.; Kenney, J. W.; Howells, P. N.; Henry, R. A. “Aspects of Homogeneous Catalysis”;. 1977,16, 3128. Nelson, J. H.; Landen, G. L.; Stevens, B. N. Synth. React. Inorg. Met.-Org. Chem. 1979, 5, 435. Nelson, J. H.; Howells, P. N.; Landen, G. L.; DeLullo, G. C.; Henry, R. A. First International Symposium on Homogeneous Catalysis, Corpus Christi, TX, Nov 29-Dec 1, 1978. “Fundamental Research in Homogeneous Catalysis”; Tsutsui, M., Ed.; Plenum: New York, 1979; pp 921-39.
5. Lacey, R. N. J. Chem. Soc. 1960, 1625 and references therein.
6. House, H. O. “Modern Synthetic Reactions”, 2nd ed; W. A. Benjamin: Menlo Park, CA, 1972; pp 596-600.
7. The actual catalyst is most likely bis(-diketonato)nickel(II) formed from Ni(acac>2 in situ by ligand exchange. This has been substantiated in the cases of the ethyl acetoacetate and iV,N-diethylaceto-acetamide reactions by electronic spectroscopy studies.*
8. Midorikawa, H. (Bull. Chem. Soc. Jpn. 1954, 27, 213) reports a 64% yield of 3-acetyl-4-(2-furyl)-3-buten-2-one with piperidine as the catalyst.
9. Saegusa, T.; Ito, Y.; Tomita, S.; Kinoshita, H. Bull. Chem. Soc. Jpn. 1972, 45, 496. Typical yields are 72-86%.
10. Trost, B. M.; Strege, P. E.; Weber, L.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978,100, 3407 and succeeding papers. Typical yields are 90-100%.