Infoscience

Journal article

The two-fold reaction benchmark applied to the copper catalyzed assembling of 1,w-difunctional hydrocarbon chains

Long-chain hydrocarbons carrying vinyl groups, chlorine atoms or oxygen functions at the terminal positions can be prepd. with excellent yields by copper mediated coupling of alkyl tosylates and Grignard reagents. E.g., Li2CuCl4 catalyzed the coupling of CH2:CH(CH2)3MgBr with TsO(CH2)nOTs (Ts = p-MeC6H4SO2; n = 5-9) to give CH2:CH(CH2)n+6CH:CH2. Li2CuCl3 catalyzed the coupling of Cl(CH2)6OTs with BrMg(CH2)nMgBr (n = 5, 6, 8) to give good yields of Cl(CH2)n+12Cl. No breeding stage is necessary if the cuprous complex dilithium trichlorocuprate rather than a cupric salt is employed as the catalyst. [on SciFinder (R)]

    Keywords: Coupling reaction (copper-mediated ; of Grignard reagents with tosylates ; difunctionalized hydrocarbon chains from) ; copper mediated coupling reaction; difunctionalized hydrocarbon chem; Grignard reagent coupling tosylate

    Note:

    CAN 115:231634

    23-1

    Aliphatic Compounds

    Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.

    Journal

    0040-4020

    written in English.

    15489-27-7; 79950-15-5 Role: CAT (Catalyst use), USES (Uses) (catalysts, for carbon-carbon coupling reactions); 34164-50-6 Role: RCT (Reactant), RACT (Reactant or reagent) (copper-mediated coupling reaction of, with alkanediol ditosylates); 71042-21-2 Role: RCT (Reactant), RACT (Reactant or reagent) (copper-mediated coupling reaction of, with bis Grignard reagents); 17036-36-1; 23708-48-7; 45037-87-4 Role: RCT (Reactant), RACT (Reactant or reagent) (copper-mediated coupling reaction of, with chlorohexanol tosylate); 73992-42-4 Role: RCT (Reactant), RACT (Reactant or reagent) (copper-mediated coupling reaction of, with pentenylmagensium bromide or with methoxymethoxy-substituted Grignard reagents); 4672-50-8; 36247-33-3 Role: RCT (Reactant), RACT (Reactant or reagent) (copper-mediated coupling reaction of, with pentenylmagnesium bromide or with methoxymethoxy-substituted Grignard reagents); 24293-28-5 (1,5-Pentanediol ditosylate); 36247-32-2; 40235-95-8 Role: RCT (Reactant), RACT (Reactant or reagent) (copper-mediated coupling reactions of, with pentenylmagnesium bromide); 34508-53-7P; 104164-59-2P; 137117-21-6P; 137117-22-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and conversion of, to Grignard reagent); 113982-53-9P; 137117-18-1P; 137117-19-2P; 137117-20-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and copper-mediated coupling reaction of, with alkanediol ditosylates); 7735-40-2P; 13560-93-5P (1,17-Octadecadiene); 20295-08-3P; 21964-50-1P (1,14-Pentadecadiene); 21964-51-2P (1,15-Hexadecadiene); 21964-52-3P (1,16-Heptadecadiene); 136561-92-7P (1,18-Nonadecadiene); 137117-11-4P (2,4,19,21-Tetraoxadocosane); 137117-12-5P (2,4,22,24-Tetraoxapentacosane); 137117-13-6P (2,4,23,25-Tetraoxahexacosane); 137117-14-7P (2,4,27,29-Tetraoxatriacontane); 137117-15-8P; 137117-16-9P; 137117-17-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 107-30-2 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with chloroalkanols); 928-51-8 (4-Chloro-1-butanol); 2009-83-8 (6-Chloro-1-hexanol); 23144-52-7 (8-Chloro-1-octanol) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with chloromethyl Me ether)

    Reference

    Record created on 2006-03-03, modified on 2016-08-08

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