A General Procedure for the Regioselective Synthesis of Aryl Thioethers and Aryl Selenides Through C–H Activation of Arenes12. Issue 18 (18th April 2013)

• Record Type: Journal Article
• Authors: Yi, Chih‐Lun; Liu, Tsung‐Jui; Cheng, Jun‐Hao; Lee, Chin‐Fa
• Is Part Of: European journal of organic chemistry. Issue 18(2013)
• Page Start: 3910
• Page End: 3918
• Publication Date: 2013-04-18
• Subjects: Sulfur -- Selenide -- C–H activation -- Arenes -- Iridium -- Copper; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300248
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A general procedure for the synthesis of aryl thioethers and aryl selenides in one‐pot through sequential iridium‐catalyzed C–H borylation and copper‐promoted C–S and C–Se bond formation is described. Functional groups including chloro, nitro, fluoro, trifluoromethyl, and nitrogen‐containing heterocycles were all tolerated under the reaction conditions. Importantly, not only aryl thiols and selenides but also their alkyl analogs were suitable coupling partners, and the products were obtained in good yields with high meta regioselectivity. Abstract : Aryl thioethers and selenides were prepared in good yields with high meta regioselectivity through sequential Ir‐catalyzed C–H borylation and Cu‐promoted C–S and C–Se bond formation in one pot. A wide range of functional groups were tolerated under the reaction conditions. In addition to aryl thiols and selenides, alkyl thiols and selenides were also suitable coupling partners in this reaction.