Direct synthesis of cyclopentadienones by cobalt carbonyl-mediated carbonylative alkyne-alkyne coupling reaction

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5785-5788

  Shibata, Takanori ^a   Ohta, Toshihiro ^a   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Alkynes; Carbonylation; Coupling reactions; Transition metals

Indexed keywords

COBALT DERIVATIVE; CYCLOPENTADIENE DERIVATIVE;

ARTICLE; ATMOSPHERIC PRESSURE; MOLECULAR INTERACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032490910     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01175-7     Document Type: Article

References (13)

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4. 4. Pearson, A. J.; Dubbert, R. J. J. Chem. Soc. Chem. Commun. 1991, 202-203; Pearson, A. J.; Shively, Jr., R. J.; Dubbert, R. A. Organometallics 1992, 11, 4096-4104; Pearson, A. J.; Shively, Jr., R. J. ibid. 1994, 13, 578-584; Pearson, A. J.; Perosa, A. ibid. 1995, 14, 5178-5183; Pearson, A. J.; Yao, X. Synlett 1997, 1281-1282.
5. 4. Pearson, A. J.; Dubbert, R. J. J. Chem. Soc. Chem. Commun. 1991, 202-203; Pearson, A. J.; Shively, Jr., R. J.; Dubbert, R. A. Organometallics 1992, 11, 4096-4104; Pearson, A. J.; Shively, Jr., R. J. ibid. 1994, 13, 578-584; Pearson, A. J.; Perosa, A. ibid. 1995, 14, 5178-5183; Pearson, A. J.; Yao, X. Synlett 1997, 1281-1282.
6. 4. Pearson, A. J.; Dubbert, R. J. J. Chem. Soc. Chem. Commun. 1991, 202-203; Pearson, A. J.; Shively, Jr., R. J.; Dubbert, R. A. Organometallics 1992, 11, 4096-4104; Pearson, A. J.; Shively, Jr., R. J. ibid. 1994, 13, 578-584; Pearson, A. J.; Perosa, A. ibid. 1995, 14, 5178-5183; Pearson, A. J.; Yao, X. Synlett 1997, 1281-1282.
7. 4. Pearson, A. J.; Dubbert, R. J. J. Chem. Soc. Chem. Commun. 1991, 202-203; Pearson, A. J.; Shively, Jr., R. J.; Dubbert, R. A. Organometallics 1992, 11, 4096-4104; Pearson, A. J.; Shively, Jr., R. J. ibid. 1994, 13, 578-584; Pearson, A. J.; Perosa, A. ibid. 1995, 14, 5178-5183; Pearson, A. J.; Yao, X. Synlett 1997, 1281-1282.
8. 5. Hübel, W.; Hoogzand, C. Chem. Ber. 1960, 93, 103-115; Krüerke, U.; Hübel, W. ibid. 1961, 94, 2829-2856.
9. 5. Hübel, W.; Hoogzand, C. Chem. Ber. 1960, 93, 103-115; Krüerke, U.; Hübel, W. ibid. 1961, 94, 2829-2856.
10. 6. Typical experimental procedure (Table 1, Entry 4) is as follows: A toluene solution (2 ml) of 1-(allyldiphenysilyl)-1-hexyne-dicobalt hexacarbonyl complex (68.2 mg, 0.12 mmol) and 1-(allyldiphenylsilyl)-1-hexyne (107.0 mg, 0.35 mmol) in a 30-ml round-bottomed flask with reflux condenser was immersed in a hot oil bath (120 °C). The reaction mixture was stirred for 2 h, then the resulting precipitates were removed by filtration through a small pad of silica gel using a mixed eluent of hexane and ethyl acetate (5/1,v/v). Purification of the crude products by thin-layer chromatography afforded pure cyclopentadienone in 99% yield (regioisomer A: 63.4 mg, 0.10 mmol, 86%, regioisomer B: 9.4 mg, 0.015 mmol, 13%).
11. L), which might control regioselectivity . (formula presented)
12. 8. Schore, N. E. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon press: Oxford, 1991; vol 5, pp. 1037-1064; Schore N. E. Comprehensive Organometalic Chemistry II; Hegedus, L. S., Ed.; Pergamon press: Oxford, 1995; vol 12. pp. 703-739.
13. 8. Schore, N. E. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon press: Oxford, 1991; vol 5, pp. 1037-1064; Schore N. E. Comprehensive Organometalic Chemistry II; Hegedus, L. S., Ed.; Pergamon press: Oxford, 1995; vol 12. pp. 703-739.