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Disclosed herein is 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. 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 showed broad substrate scope with good to excellent yields. [ABSTRACT FROM AUTHOR]

An efficient synthesisof 2-aryl 4-substituted quinolines fromstable and readily available o-cinnamylanilines,prepared from anilines and cinnamylalcohols, has been developed. Thereaction occurred via a regioselective 6-endo-trigintramolecular oxidative cyclization using KOtBu as amediator and DMSO as an oxidant at rt. The reaction showed a broadsubstrate scope with good to excellent yields. [ABSTRACT FROM AUTHOR]

Anefficient strategy for the synthesis of 3-substituted 2-benzylindolesfrom stable and readily available o-allylanilines,prepared from anilines and allyl alcohols, has been developed. Thereaction occurred via a regioselective 5-exo-trigintramolecular oxidative cycloisomerization using Pd(OAc)2as catalyst and molecular oxygen as an oxidant. The reaction showeda broad substrate scope with good to excellent yields. [ABSTRACT FROM AUTHOR]

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]