• 제목/요약/키워드: Allylic substitution

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Allylic fluorination

  • Park, Oee-Sook;Son, Hoe-Joo;Lee, Woo-Young
    • Archives of Pharmacal Research
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    • 제10권4호
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    • pp.239-244
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    • 1987

  • An efficient and inexpensive method for the substitution of allylic hydroxyl group with fluoride, without allylic rearrangement, and elimination was developed. This method consists of treating an allylic alcohol with methylithium, followed by p-toluene sulfonyl fluoride, lithium fluoride and 12-Crown-4. This methodology was proved to be efficient by preparting geranyl fluoride, neryl fluoride, cinnamyl fluoride, E, E-farnesyl fluoride, retinyl fluoride and 4-fluoro-2-methyl-6-(ptolyl)-2-heptene.

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Pd-Catalyzed Substitution Reactions with Organoindium Reagents in situ Generated from Indium and Allyl or Propargyl Halides

  • Lee, Phil-Ho;Shim, Eun-Kyong;Lee, Koo-Yeon;SeoMoon, Dong;Kim, Sun-Dae
    • Bulletin of the Korean Chemical Society
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    • 제26권1호
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    • pp.157-160
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    • 2005

  • Allylindium and propargylindium reagents in situ generated from the reactions of indium with allyl halides and propargyl halides could participate as nucleophiles in Pd-catalyzed substitution reactions of allyl carbonates to produce 1,5-dienes and 1,5-enynes in good yields. $\beta$-Hydride elimination products were produced in case of carbonates having $\beta$-hydrogens. Because organoindium reagents obtained from allyl or propargyl halides and indium have previously not been used to Pd-catalyzed allylic and propargylic substitution reactions, these results should provide more opportunities for the development of new C-C bond forming reactions.

  • https://doi.org/10.5012/bkcs.2005.26.1.157 인용 PDF KSCI