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)]
1991
47
32
6287
92
CAN 115:231634
23-1
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
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)
REVIEWED
EPFL