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An efficient synthetic route for the synthesis of functionalized 2-benzyl benzo[b]furans via a regioselective 5-exo-trig intramolecular oxidative cyclization of ortho-cinnamyl phenols using [PdCl2(CH3CN)2] as catalyst and benzoquinone as an oxidant, is disclosed. Further, a sequential ortho-cinnamylation of phenols using cinnamyl alcohols catalyzed by Re2O7, followed by an oxidative cyclization using the above Pd catalyst, is performed. The reaction shows broad substrate scope with good to excellent yields.

The article describes a unique dehydrative C- C bond formation between unprotected anilines with benzyl alcohols. [Re.sub.2][O.sub.7] is used as a catalyst which provides C-benzylanilines with high to excellent yields and good chemoselectivities.

An unprecedented dehydrative C-C bond formation between unprotected anilines with benzyl alcohols is disclosed. Re2O7 catalyst (5 mol %) at elevated reaction temperature (80 °C) provided C-benzylanilines with high to excellent yields and with good chemoselectivities (over N-alkylation). A probable mechanism has been proposed based on mechanistic studies. [ABSTRACT FROM AUTHOR]