Organic Letters p. 4777 - 4779 (2005)
Update date:2022-08-03
Topics: Nucleophilic substitution Chemical Synthesis Amidation Rapid Synthesis Indolines and Indoles Heterocyclic ring Domino amidation Anhydrolycorinone, hippadine, oxoassoanine, and pratosine Inductive effects
Ganton, Michael D.
Kerr, Michael A.
(Chemical Equation Presented) When subjected to palladium-catalyzed amidation conditions, 2-triflyloxy phenethyl carbonates undergo, in addition to the expected aryl cross-coupling, an additional amidation with net displacement of the carbonate. The result is a one-step synthesis of indolines which may be oxidized to indoles. The utility of the procedure is illustrated by the two- or three-step syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine.
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