4792-79-4Relevant articles and documents
ARENE COMPLEXES OF TRANSITION METALS IN REACTIONS WITH NUCLEOPHILIC REAGENTS. XVII. NUCLEOPHILIC SUBSTITUTION OF THE FLUORINE ATOM BY ALKOXY GROUPS, CATALYZED BY THE (η-BENZENE)(η-ETHYLTETRAMETHYLCYCLOPENTADIENYL)RHODIUM(III) DICATION, IN THE REACTION OF FLUOROARENES WITH ALCOHOLS
Goryunov, L. I.,Litvak, V. V.,Shteingarts, V. D.
, p. 354 - 358 (2007/10/02)
Effective catalysis by the (2+)2 complex, discovered earlier in the case of methoxydefluorination, occurs during the nucleophilic substitution of a fluorine atom by a alkoxy groups in the reactions of fluoroarenes with a wide range of alcohols in the absence of alkalis.By means of fluorobenzene it was established that the accumulation rate of the ethers depends substantially on the structure of the nucleophile and increases in the following order: PhCH2OH -CH2OH ClCH2CH2OH = sec-C3H7OH, sec-C4H9OH, cyclo-C6H11OH HO)CH2)nOH (n = 3-5) iso-C4H9OH = AlkOH (Alk = Me, Et, Pr, Bu, Am).For the case of the production of the compounds C10H21OC6H5 and C16H33O-2,4,6-Me3C6H2 it was shown that higher alkyl aryl ethers can be synthesized with yields of 65-70percent, calculated on the fluoroarene, and up to 900percent calculated on the catalyst.By the synthesis of benzodioxane in the reaction of o-fluorophenol with 2-chloroethanol it was demonstrated that heterocyclic compounds can be obtained if bifunctional substrates and reagents are used.
