Oxidative Biaryl Coupling Reaction of Phenol Ether Derivatives Using a Hypervalent Iodine(III) Reagent

Abstract

The hypervalent iodine(III)-induced intramolecular biaryl coupling reaction of phenol ether derivatives (nonphenolic derivatives) was investigated with the aim of preparing various dibenzo heterocyclic compounds. 1,3-Diarylpropanes (1a−e), N-benzyl-N-phenethylamines (2a−c) and N,N-dibenzylamines (3a−e) react with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), containing BF3·Et2O in CH2Cl2 to give the biaryl coupling products (4−6) in good yield. As an application of the reaction, we examined the synthesis of oxygen- and sulfur-containing dibenzoheterocyclic compounds (12−15), whose side chain moiety could be easily cleaved by the known method to give 2,2‘-substituted biphenyl compounds (16−18).