Palladium‐Catalyzed Fluorosulfonylvinylation of Organic Iodides. Issue 17 (29th March 2017)

• Record Type: Journal Article
• Authors: Zha, Gao‐Feng; Zheng, Qinheng; Leng, Jing; Wu, Peng; Qin, Hua‐Li; Sharpless, K. Barry
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 17(2017)
• Page Start: 4849
• Page End: 4852
• Publication Date: 2017-03-29
• Subjects: alkenes -- click chemistry -- drug discovery -- fluorine -- palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201701162
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A palladium‐catalyzed fluorosulfonylvinylation reaction of organic iodides is described. Catalytic Pd(OAc)2 with a stoichiometric amount of silver(I) trifluoroacetate enables the coupling process between either an (hetero)aryl or alkenyl iodide with ethenesulfonyl fluoride (ESF). The method is demonstrated in the successful syntheses of eighty‐eight otherwise difficult to access compounds, in up to 99 % yields, including the unprecedented 2‐heteroarylethenesulfonyl fluorides and 1, 3‐dienylsulfonyl fluorides. Abstract : Adding a fluorosulfonylvinyl group : Catalytic Pd(OAc)2 with a stoichiometric amount of silver(I) trifluoroacetate enables the coupling process between either an (hetero)aryl or alkenyl iodide with ethenesulfonyl fluoride. The method is demonstrated in the successful syntheses of eighty‐eight otherwise difficult to access compounds, in up to 99 % yields. The method does not require base, phosphine ligand, anhydrous solvent, or an inert atmosphere.