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

doi:10.1021/ol401234v

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

22 Citations (SciVal)

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 language	English
Pages (from-to)	3050-3053
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	12
DOIs	https://doi.org/10.1021/ol401234v
Publication status	Published - 4 Jun 2013

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

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.",

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T1 - Palladium-catalyzed arylic/allylic amination: permutable domino sequences for the synthesis or dihydroquinolines from Morita-Baylis-Hillman adducts

AU - Gasperini, Danila

AU - Lorion, Melanie M.

AU - Oble, Julie

AU - Poli, Giovanni

PY - 2013/6/4

Y1 - 2013/6/4

N2 - 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.

AB - 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.

U2 - 10.1021/ol401234v

DO - 10.1021/ol401234v

M3 - Article

VL - 15

SP - 3050

EP - 3053

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 12

ER -

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

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