Chemical Society of JapanActa Medica Okayama036670224832019 Copper-catalyzed Regioselective Chloroamination of Alkenes with Chlorotrimethylsilane and N-Fluorobenzenesulfonimide under Microwave-assisted Conditions281283ENMasayukiIwasakiResearch Institute for Interdisciplinary Science, Okayama UniversityJieXuGraduate School of Natural Science and Technology, Okayama UniversityYukariTaniGraduate School of Natural Science and Technology, Okayama UniversityLiyanFuGraduate School of Natural Science and Technology, Okayama UniversityYuichiIkemotoGraduate School of Natural Science and Technology, Okayama UniversityYasuyukiUraDepartment of Chemistry, Biology, and Environmental Science, Faculty of Science, Nara Women’s UniversityYasushiNishiharaResearch Institute for Interdisciplinary Science, Okayama University A copper-catalyzed chloroamination of alkenes with chlorotrimethylsilane and N-fluorobenzenesulfonimide has been developed. The reactions were complete within 1 h at 120 degrees C by means of microwave heating. The present chloroamination proceeds with a perfect regioselectivity and is compatible with various functional groups. The preliminary mechanistic investigation revealed that the reaction involves a radical process. The utility of the present method was demonstrated by scalable, operationally simple and safe system.No potential conflict of interest relevant to this article was reported.Chemical Society of JapanActa Medica Okayama036670224782018Cu/Fe/O=PPh3-Catalyzed Etherification for the Synthesis of Aryl 3-Benzo[b]thienyl Ethers10441047ENKoichiMitsudoDivision of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama UniversityTakuyaAsadaDivision of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama UniversityTomohiroInadaDivision of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama UniversityYujiKurimotoDivision of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama UniversityHirokiMandaiDivision of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama UniversitySeijiSugaDivision of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University Cu/Fe-cocatalyzed cross-coupling reactions between 3-bromobenzo[b]thiophene and hydroxyaryls are described herein. The combination of Cu and Fe catalysts is important for the progress of the reactions, and the use of triphenylphosphine oxide as a ligand suppresses the dehalogenation of 3-bromobenzo[b]thiophene, and promptly facilitates the reaction. The obtained aryl benzo[b]thienyl ethers can be converted to pextended thienobenzofuran derivatives via Pd-catalyzed dehydrogenative cyclizations.No potential conflict of interest relevant to this article was reported.