Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes
A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.
Bering, Luis,Jeyakumar, Kirujan,Antonchick, Andrey P.
supporting information
p. 3911 - 3914
(2018/07/22)
Friedel-Crafts Arylmethylation of Aromatics with Bis(chloromethyl)benzenes Catalysed by Zinc Chloride Supported on Silica Gel
In the Friedel Crafts arylmethylation of aromatics with bis(chloromethyl)benzenes using strong Lewis acids (e.g. AlCl3, FeCl3), many side reactions such as transalkylation, dealkylation and polymerization are generally difficult to avoid; however, a similar reaction using silica gel-supported zinc chloride selectively gives a monoarylmethylated compound in high yield.
Kodomari, Mitsuo,Taguchi, Shinkichi
p. 240 - 241
(2007/10/03)
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