RT Journal Article
T1 Palladium-catalyzed aminocyclization-coupling cascades: preparation of dehydrotryptophan derivatives and computational study
A1 Vaz Araujo, Belén
A1 Martínez Fernández, Claudio
A1 Cruz, Francisco
A1 Denis Vasconcellos, Juan Gabriel
A1 Rodríguez de Lera, Ángel
A1 Aurrecoechea, José M.
A1 Álvarez Rodríguez, Maria Rosana
K1 2306.15 Mecanismos de Reacción
K1 2306.11 Compuestos Organometálicos
AB Dehydrotryptophan derivatives have been preparedby palladium-catalyzed aminocyclization-Heck-type coupling cas-cades starting from o-alkynylaniline derivatives and methyl α-aminoacrylate. Aryl, alkyl (primary, secondary, and tertiary), andalkenyl substituents have been introduced at the indole C-2position. Further variations at the indole benzene ring, as well asthe C-2-unsubstituted case, have all been demonstrated. In the caseof C-2 aryl substitution, the preparation of the o-alkynylanilinesubstrate by Sonogashira coupling and the subsequent cyclization−coupling cascade have been performed in a one-pot protocol with asingle catalyst. DFT calculations have revealed significant differ-ences in the reaction profiles of these reactions relative to thoseinvolving methyl acrylate or methacrylate, and between the reactions of the free anilines and their corresponding carbamates. Thosecalculations suggest that the nature of the alkene and of the acid HX released in the HX/alkene exchange step that precedes C−Cbond formation could be responsible for the experimentally observed differences in reaction efficiencies.
PB The Journal of Organic Chemistry
SN 00223263
YR 2021
FD 2021-07-02
LK http://hdl.handle.net/11093/3303
UL http://hdl.handle.net/11093/3303
LA eng
NO The Journal of Organic Chemistry, 86(13): 8766-8785 (2021)
NO Financiado para publicación en acceso aberto: Universidade de Vigo/CISUG
NO Euskal Herriko Unibertsitatea | Ref. PES18/89
DS Investigo
RD 13-ene-2025