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Two unprecedented N functionalizations of indoles with ynamides are described. By varying the electron‐withdrawing group on the ynamide nitrogen atom, either Z‐indolo‐etheneamides or indolo‐amidines can be selectively obtained under the same metal‐free reaction conditions. The scope and synthetic potential of these reactions, as well as some mechanistic insights provided by DFT calculations, are reported.
Zweifach variabel: Eine effiziente intermolekulare Oxyamidierung von Indolen beruht auf dem Einsatz von Rhodium(II)‐katalysierten Nitren‐Transfers. Durch Wechsel des Nucleophils kann die Reaktion selektiv zu den cis‐ oder trans‐Produkten geführt werden. Auch die Regioselektivität der Addition kann gesteuert werden, indem man den Substituenten an der Indol‐Doppelbindung variiert (siehe Schema).
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