3 years ago

Metal-Free Formal Oxidative C−C Coupling by In Situ Generation of an Enolonium Species

Metal-Free Formal Oxidative C−C Coupling by In Situ Generation of an Enolonium Species
Daniel Kaiser, Saad Shaaban, Nuno Maulide, Aurélien de la Torre
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. 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.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201701538

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