Intramolecular Palladium(II)-catalyzed 6-endo C-H alkenylation directed by the remote N-protecting group: Mechanistic Insight and Application to the Synthesis of Dihydroquinolines

Asier Carral-Menoyo, L Sotorríos, Verónica Ortiz-de-Elguea, Aitor Diaz-Andrés, Nuria Sotomayor, Enrique Gómez-Bengoa, Esther Lete

Research output: Contribution to journalArticlepeer-review

Abstract

A protocol for the Pd(II)-catalyzed C–H alkenylation reaction of substituted N-allylanilines via an unusual 6-endo process has been developed. A density functional theory (DFT) study of the mechanistic pathway has shown that the coordination of the remote protecting group to the palladium center is determinant for the control of the regioselectivity in favor of the 6-endo process. The reaction would proceed via prior activation of the alkene. This procedure constitutes a mild and efficient method for the synthesis of 1,4-dihydroquinoline derivatives from simple and readily accessible substrates.
Original languageEnglish
Pages (from-to)2486–2503
Number of pages18
JournalThe Journal of organic chemistry
Volume85
Issue number4
Early online date30 Dec 2019
DOIs
Publication statusPublished - 21 Feb 2020

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