title: Rhodium-Catalyzed C-S and C-N Functionalization of Arenes: Combination of C-H Activation and Hypervalent Iodine Chemistry.
abstract: Rhodium-catalyzed sulfonylation, thioetherification, thiocyanation, and other heterofunctionalizations of arenes bearing a heterocyclic directing group have been realized. The reaction proceeds by initial Rh(III) -catalyzed C-H hyperiodination of arene at room temperature followed by uncatalyzed nucleophilic functionalization. A diaryliodonium salt is isolated as an intermediate, which represents umpolung of the arene substrate, in contrast to previous studies that suggested umpolung of the coupling partner.
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (China).
authors.forename: Fen
authors.initials: F
authors.lastname: Wang
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (China).
authors.forename: Xinzhang
authors.initials: X
authors.lastname: Yu
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (China).
authors.forename: Zisong
authors.initials: Z
authors.lastname: Qi
authors.affiliation: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (China). xwli@dicp.ac.cn.
authors.forename: Xingwei
authors.initials: X
authors.lastname: Li
keywords: CH activation; homogeneous catalysis; hypervalent iodine; rhodium; umpolung