811784-21-1Relevant articles and documents
A novel synthetic route to 2-arylalkanoic acids by a ruthenium-catalyzed chemoselective oxidation of furan rings
Noji, Masahiro,Sunahara, Haruka,Tsuchiya, Ken-Ichi,Mukai, Toru,Komasaka, Ayako,Ishii, Keitaro
experimental part, p. 3835 - 3845 (2009/07/04)
An efficient two-step synthesis of 2-arylalkanoic acids from 1-arylalkanols is described. Firstly, 1-arylalkylfuran derivatives were synthesized in high yields by the metal triflate catalyzed Friedel-Crafts alkylation of 2-methylfuran with 1-arylalkanols without employing anhydrous conditions. The chemoselective oxidation of the furan ring in 1-arylalkylfurans to carboxylic acid was then investigated. In a solvent system of hexane-EtOAc/H2O (1:3:4), the furan ring was selectively oxidized with 7 equivalents of NaIO 4 by using 0.5 mol% RuCl3 as catalyst to give 2-arylalkanoic acids in good yields. The selectivity of ruthenium oxidation was controlled by the solvent ratio of hexane-EtOAc. Georg Thieme Verlag Stuttgart.
Br?nsted-acid-catalyzed coupling of electron-rich arenes with substituted allylic and secondary benzylic alcohols
Le Bras, Jean,Muzart, Jacques
, p. 7942 - 7948 (2008/02/08)
p-Toluenesulfonic acid and triflic acid catalyze efficiently the coupling of electron-rich arenes with allylic and benzylic alcohols. Reactions are conducted under mild conditions, in air, and in the absence of solvent.
METHOD FOR ESTABLISHING CC BONDS BETWEEN ELECTROPHILIC SUBSTRATES AND ? - NUCLEOPHILES IN NEUTRAL TO ALKALINE AQUEOUS OR ALCOHOLIC SOLVENTS WITHOUT USING A LEWIS OR BRONSTED ACID
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Page/Page column 14, (2008/06/13)
The invention relates to a method for establishing carbon-carbon bonds by reacting electropohilic substrates that have a solvolysis rate kEtOH (25°C) > 10-6 s-1 and ? compounds. The method is characterized by generating the intermediary carbocations in neutral to alkaline aqueous or alcoholic solvents or solvent mixtures without using a Lewis or Br?nsted acid.
Electrophilic alkylations in neutral aqueous or alcoholic solutions
Hofmann, Matthias,Hampel, Nathalie,Kanzian, Tanja,Mayr, Herbert
, p. 5402 - 5405 (2007/10/03)
Acid-free Friedel-Crafts chemistry: A paradox? Nucleophilicity scales, based on reactions with benzhydrylium ions, show that many π systems are more nucleophilic than aqueous or alcoholic solutions that are generally employed as solvents for SN1 reactions. Solvolytically generated carbocations can, therefore, be trapped by donor-substituted arenes and alkenes to form products of Friedel-Crafts-type reactions in neutral aqueous solutions (see scheme).