Metal‐Free Formal Oxidative C−C Coupling by In Situ Generation of an Enolonium Species. Issue 21 (21st April 2017)

• Record Type: Journal Article
• Authors: Kaiser, Daniel; de la Torre, Aurélien; Shaaban, Saad; Maulide, Nuno
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 21(2017)
• Page Start: 5921
• Page End: 5925
• Publication Date: 2017-04-21
• Subjects: amide activation -- chemoselectivity -- keteniminium ions -- oxidative C−C coupling -- umpolung; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201701538
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Much contemporary organic synthesis relies on transformations that are driven by the intrinsic, so‐called "natural", polarity of chemical bonds and reactive centers. The design of unconventionally polarized synthons is a highly desirable strategy, as it generally enables unprecedented retrosynthetic disconnections for the synthesis of complex substances. Whereas the umpolung of carbonyl centers is a well‐known strategy, polarity reversal at the α‐position of a carbonyl group is much rarer. Herein, we report the design of a novel electrophilic enolonium species and its application in efficient and chemoselective, metal‐free oxidative C−C coupling. Abstract : Umpole me : The design of unconventionally polarized synthons is a highly desirable strategy in synthesis. While the umpolung of carbonyl centers is a well‐known strategy, polarity reversal at the α‐position to a carbonyl group is much rarer. The design of a novel electrophilic enolonium species for chemoselective, metal‐free oxidative C−C coupling is now reported.