Palladium-catalyzed arylic/allylic amination: permutable domino sequences for the synthesis or dihydroquinolines from Morita-Baylis-Hillman adducts

Danila Gasperini, Melanie M. Lorion, Julie Oble, Giovanni Poli

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

An efficient palladium-catalyzed synthesis of 1,2-dihydroquinolines has been developed via the reaction between anilines and Morita–Baylis–Hillman adducts derived from o-bromobenzaldehyde. This new Pd(0)-catalyzed pseudo-domino type I sequence involves a Buchwald–Hartwig arylic amination and an allylic amination. When starting from an o-bromo allylic alcohol, the chronology is arylic amination/allylic arylation. However, the sequence reverses when the reaction is performed on the corresponding o-bromo allylic acetate.
Original languageEnglish
Pages (from-to)3050-3053
Number of pages4
JournalOrganic Letters
Volume15
Issue number12
DOIs
Publication statusPublished - 4 Jun 2013

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