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Organic Letters
Volumn 10, Issue 12, 2008, Pages 2389-2392
Efficient preparation of terminal conjugated dienes by coupling of dienol phosphates with grignard reagents under iron catalysis
Author keywords

[No Author keywords available]
Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IRON; PHEROMONE; POLYENE;
EID: 48849106777     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800816f     Document Type: Article
Times cited : (80)
References (81)
  • 3
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    • Only very few examples of cross-coupling reactions with halo-1,3-butadienes have been reported. (a) The coupling of 1-octyne with the (Z)-and (E)-1-chloro-1,3-butadienes under the Sonogashira conditions: Huynh, C.; Alami, M.; Linstrumelle, G. Synth. Commun. 1994, 24, 2273.
    • Only very few examples of cross-coupling reactions with halo-1,3-butadienes have been reported. (a) The coupling of 1-octyne with the (Z)-and (E)-1-chloro-1,3-butadienes under the Sonogashira conditions: Huynh, C.; Alami, M.; Linstrumelle, G. Synth. Commun. 1994, 24, 2273.
  • 5
    • 0026725539 scopus 로고    scopus 로고
    • The Ni-catalyzed coupling reaction of (Z)-1- heptenylcyanocuprate with 1-bromo-1,3-butadiene, which leads to 65% yield of (E,Z)-1,3,5-undecatriene: Alexakis, A.; Barthel, A. M.; Normant, J. F.; Fugier, C.; Leroux, M. Synth. Commun. 1992, 22, 1839.
    • (b) The Ni-catalyzed coupling reaction of (Z)-1- heptenylcyanocuprate with 1-bromo-1,3-butadiene, which leads to 65% yield of (E,Z)-1,3,5-undecatriene: Alexakis, A.; Barthel, A. M.; Normant, J. F.; Fugier, C.; Leroux, M. Synth. Commun. 1992, 22, 1839.
  • 6
    • 59949086803 scopus 로고    scopus 로고
    • The Ni-catalyzed coupling of chloroprene with PhMgBr (yield 65%): Tamao, K.; Sumitani, K.; Zembayashi, M.; Fujioka, A.; Kodama, S.-i.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958.
    • (c) The Ni-catalyzed coupling of chloroprene with PhMgBr (yield 65%): Tamao, K.; Sumitani, K.; Zembayashi, M.; Fujioka, A.; Kodama, S.-i.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958.
  • 7
    • 0011708612 scopus 로고    scopus 로고
    • 2MgCl: Sakurai, H.; Hosomi, A.; Saito, M.; Sasaki, K.; Iguchi, H.; Sasaki, J.-i.; Araki, Y. Tetrahedron 1983, 39, 883.
    • 2MgCl: Sakurai, H.; Hosomi, A.; Saito, M.; Sasaki, K.; Iguchi, H.; Sasaki, J.-i.; Araki, Y. Tetrahedron 1983, 39, 883.
  • 9
    • 0344923845 scopus 로고    scopus 로고
    • To the best of our knowledge, no example of cross-coupling reaction from terminal dienyl phosphates has been reported. For a nickel-catalyzed coupling of nonterminal dienyl phosphate with Grignard reagents, see
    • To the best of our knowledge, no example of cross-coupling reaction from terminal dienyl phosphates has been reported. For a nickel-catalyzed coupling of nonterminal dienyl phosphate with Grignard reagents, see: Sofia, A.; Karlström, E.; Itami, K.; Bäckvall, J.-E. J. Org. Chem. 1999, 64, 1745.
    • (1999) J. Org. Chem , vol.64 , pp. 1745
    • Sofia, A.1    Karlström, E.2    Itami, K.3    Bäckvall, J.-E.4
  • 52
    • 59949090855 scopus 로고    scopus 로고
    • 3 (1 mol%, 0.25 mmol) in THF (50 mL). The dienol phosphate (25 mmol) was added at once under stirring, and then the Grignard reagent (30 mmol) was added dropwise for 20 min. After 15 min, the reaction mixture was quenched with a 1 M aqueous HCl solution (50 mL). The aqueous phase was extracted with cyclohexane (3 x 30 mL), dried with MgSO4, and concentrated under reduced pressure. The product was purified by distillation or by column chromatography (see Supporting Information).
    • 3 (1 mol%, 0.25 mmol) in THF (50 mL). The dienol phosphate (25 mmol) was added at once under stirring, and then the Grignard reagent (30 mmol) was added dropwise for 20 min. After 15 min, the reaction mixture was quenched with a 1 M aqueous HCl solution (50 mL). The aqueous phase was extracted with cyclohexane (3 x 30 mL), dried with MgSO4, and concentrated under reduced pressure. The product was purified by distillation or by column chromatography (see Supporting Information).
  • 56

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