Studies on the Synthesis of Aryl Ethers Using Arene-Manganese Chemistry

Article abstract of DOI:10.1021/jo00025a026

Selective arylation of polyfunctional phenols, using chlorobenzene- and p-chlorotoluene-manganese tricarbonyl cations, is described.The intermediate arene-manganese complexes are found to undergo stereo- and regioselective reactions with Schoellkopf's chiral glycine enolate equivalent to give dienyl-Mn(CO)3 complexes.Treatment of these complexes with N-bromosuccinimide at room temperature, followed by hydrolysis of the dihydropyrazine, gives diaryl ethers in which one of the aromatic rings is an arylglycine methyl ester.