Metal-Free Formal Oxidative C?C Coupling by In?Situ Generation of an Enolonium Species |
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Authors: | Daniel Kaiser Dr Aurélien de?la?Torre Saad Shaaban Prof?Dr Nuno Maulide |
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Institution: | 1. Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Wien, Austria;2. Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Wien, Austria
These authors contributed equally to this work. |
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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. |
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Keywords: | amide activation chemoselectivity keteniminium ions oxidative C?C coupling umpolung |
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