Palladium‐Catalyzed Oxidative Synthesis of α‐Acetoxylated Enones from Alkynes. Issue 19 (6th April 2016)

• Record Type: Journal Article
• Authors: Jiang, Tuo; Quan, Xu; Zhu, Can; Andersson, Pher G.; Bäckvall, Jan‐E.
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 19(2016)
• Page Start: 5824
• Page End: 5828
• Publication Date: 2016-04-06
• Subjects: alkynes -- enones -- oxidation -- palladium -- sulfoxides; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201600696
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We report a palladium‐catalyzed oxidative functionalization of alkynes to generate α‐acetoxylated enones in one step. A range of functional groups are well‐tolerated in this reaction. Mechanistic studies, including the use of 18 O‐labeled DMSO, revealed that the ketone oxygen atom in the product originates from DMSO. Abstract : Combating oxygen deficiency : A one‐step protocol has been developed for the palladium‐catalyzed conversion of simple alkynes into α‐acetoxylated enones under oxidative conditions (see scheme; BQ=1, 4‐benzoquinone). A wide range of functional groups are tolerated in the reaction. Mechanistic studies with [ 18 O]DMSO revealed that the ketone oxygen atom in the product originates from DMSO.