Metal catalyzed cross coupling reaction in organic synthesis

An efficient, simple, and economically attractive copper catalyzed synthesis of a wide range of 2-arylbenzo[b]furans through domino intermolecular C(aryl)-C(alkynyl) bond formation followed by intramolecular C(alkynyl)-O bond formation from coupling of o-iodophenols with aryl acetylenes is put forward. o-Iodophenols containing electron-withdrawing groups provided better yields for benzofurans than o-iodophenols containing electron-releasing groups. The aryl terminal alkynes containing electron-releasing groups yielded better yields for benzo[b]furans than alkynes containing electron-withdrawing group. BINAM-CuCl ₂ could be used as an efficient catalyst for the synthesis of 2-substituted benzothiazoles by intramolecular cyclization through C(aryl)-S bond formation at 82°C from very less reactive N-(2-chlorophenyl)benzothioamide or N-(2-bromophenyl)benzothioamide. This is an abstract of a paper submitted at the 21st Annual Saudi-Japan Symposium on Catalysts in Petroleum Refining and Petrochemicals (Dhahran, Saudi Arabia 11/27-28/2011).