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Volumn 53, Issue 9, 1997, Pages 3027-3034

Cross-coupling and carbonylative cross-coupling of organofluorosilanes with hypervalent iodonium tetrafluoroborates

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BIPHENYL; KETONE;

EID: 0031550877     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00043-4     Document Type: Article
Times cited : (29)

References (48)
  • 9
    • 0011299922 scopus 로고    scopus 로고
    • note
    • (b) The 2-(phenyl)thiopheneiodonium tetrafluoroborate (11) was prepared by adaptation of the procedure reported by M. Ochiai.
  • 10
    • 0026522397 scopus 로고
    • Preparation of 1-phenyl-2-(dimethylfluorosilyl)acetylene (5): To a stirred solution of phenylacetylene (15 mL, 137 mmol) in THF (100 mL) was slowly added butyllithium (2.5 M in hexanes, 60.3 mL, 150 mmol) at -78 °C. The reaction mixture was stirred at room temperature for 10 min. And dichloromethylsilane (28.2 mL, 205 mmol) was added followed by adding copper (II) fluoride trihydrate (9 g, 54.8 mmol). The solvent and other volatiles were evaporated in vacuo. The crude product was separated by distillation (b.p. 83-84 °C/9 mmHg) to give 5 (14.1 g, 58%)
    • 4. The compounds 3a, 3b, and 5 were prepared by a modified procedure reported in the literature, see, Hatanaka, Y.; Fukushima, S.; Hiyama, T. Tetrahedron 1992, 48, 2113-2126. Preparation of 1-phenyl-2-(dimethylfluorosilyl)acetylene (5): To a stirred solution of phenylacetylene (15 mL, 137 mmol) in THF (100 mL) was slowly added butyllithium (2.5 M in hexanes, 60.3 mL, 150 mmol) at -78 °C. The reaction mixture was stirred at room temperature for 10 min. And dichloromethylsilane (28.2 mL, 205 mmol) was added followed by adding copper (II) fluoride trihydrate (9 g, 54.8 mmol). The solvent and other volatiles were evaporated in vacuo. The crude product was separated by distillation (b.p. 83-84 °C/9 mmHg) to give 5 (14.1 g, 58%).
    • (1992) Tetrahedron , vol.48 , pp. 2113-2126
    • Hatanaka, Y.1    Fukushima, S.2    Hiyama, T.3
  • 14
    • 33845555198 scopus 로고
    • (b) Tamao, K.; Yoshida, J.; Yamamoto, H.; Kakui, T.; Matsumoto, H.; Kumada, M. Organometallics 1982, 1, 355-368. Fluorination: Tamao, K.; Kakui, T.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983-990. Preparation of (E)-β-dimethylfluorosilylstyrene (4a): To a stirred solution of chlorodimethylsilane (12.0 g, 117 mmol) and 3 or 4 drops of hexachloroplatinic acid in THF (10 mL) was slowly added phenylacetylene (8.0 g, 78 mmol) at a rate such that a steady reflux was maintained. The reaction mixture was stirred for 4 hours and copper (II) fluoride trihydrate (7.28 g, 46.8 mmol) was added in situ. The solvent and other volatiles were evaporated in vacuo. The crude product was separated by distillation (b.p. 60-64 °C/0.7 mmHg) to give 4a (8.43 g, 60%).
    • (1982) Organometallics , vol.1 , pp. 355-368
    • Tamao, K.1    Yoshida, J.2    Yamamoto, H.3    Kakui, T.4    Matsumoto, H.5    Kumada, M.6
  • 15
    • 0000497149 scopus 로고
    • Preparation of (E)-β-dimethylfluorosilylstyrene (4a): To a stirred solution of chlorodimethylsilane (12.0 g, 117 mmol) and 3 or 4 drops of hexachloroplatinic acid in THF (10 mL) was slowly added phenylacetylene (8.0 g, 78 mmol) at a rate such that a steady reflux was maintained. The reaction mixture was stirred for 4 hours and copper (II) fluoride trihydrate (7.28 g, 46.8 mmol) was added in situ. The solvent and other volatiles were evaporated in vacuo. The crude product was separated by distillation (b.p. 60-64 °C/0.7 mmHg) to give 4a (8.43 g, 60%)
    • (b) Tamao, K.; Yoshida, J.; Yamamoto, H.; Kakui, T.; Matsumoto, H.; Kumada, M. Organometallics 1982, 1, 355-368. Fluorination: Tamao, K.; Kakui, T.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983-990. Preparation of (E)-β-dimethylfluorosilylstyrene (4a): To a stirred solution of chlorodimethylsilane (12.0 g, 117 mmol) and 3 or 4 drops of hexachloroplatinic acid in THF (10 mL) was slowly added phenylacetylene (8.0 g, 78 mmol) at a rate such that a steady reflux was maintained. The reaction mixture was stirred for 4 hours and copper (II) fluoride trihydrate (7.28 g, 46.8 mmol) was added in situ. The solvent and other volatiles were evaporated in vacuo. The crude product was separated by distillation (b.p. 60-64 °C/0.7 mmHg) to give 4a (8.43 g, 60%).
    • (1983) Tetrahedron , vol.39 , pp. 983-990
    • Tamao, K.1    Kakui, T.2    Yoshida, J.3    Kumada, M.4
  • 43
    • 0026103949 scopus 로고
    • 17. Goto, Y.; Hayashi, A.; Kimura, Y.; Nakayama, M.; J. Cryst. Growth. 1991, 108, 688-698. [Chem. Abstr. 114, 1991, 217435c]
    • (1991) Chem. Abstr. , vol.114
  • 46
    • 4243559642 scopus 로고
    • 19. Elokhina, V. N.; Nakhmanovich, A. S.; Bannikova, O. B.; Izv. Akad. Nauk. SSSR. Ser. Khim. 1990, 2637-2640. [Chem. Abstr. 114, 1991, 122282m]
    • (1991) Chem. Abstr. , vol.114
  • 47
    • 0003601534 scopus 로고
    • Merck & Co. Inc., Rahway, N.J., and references cited therein
    • 20. "The Merck Index 11th Edition, M. Windholz, Ed., Merck & Co. Inc., Rahway, N.J., 1989, p 3314, and references cited therein.
    • (1989) The Merck Index 11th Edition , pp. 3314
    • Windholz, M.1
  • 48
    • 0003601534 scopus 로고
    • Merck & Co. Inc., Rahway, N.J., and references cited therein
    • 21. "The Merck Index 11th Edition, M. Windholz, Ed., Merck & Co. Inc., Rahway, N.J., 1989, p 3320, and references cited therein.
    • (1989) The Merck Index 11th Edition , pp. 3320
    • Windholz, M.1


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