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钯催化的芳基/烯丙基胺化反应:从 Morita-Baylis-Hillman 加合物到二氢喹啉的可互换的多米诺序列合成。

Palladium-catalyzed arylic/allylic aminations: permutable domino sequences for the synthesis of dihydroquinolines from Morita-Baylis-Hillman adducts.

机构信息

UPMC Univ. Paris 06, Sorbonne Universités , Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), case 183, 4 place Jussieu, 75005 Paris, France.

出版信息

Org Lett. 2013 Jun 21;15(12):3050-3. doi: 10.1021/ol401234v. Epub 2013 Jun 4.

DOI:10.1021/ol401234v
PMID:23734985
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.

摘要

通过苯胺与由邻溴苯甲醛衍生的 Morita-Baylis-Hillman 加合物之间的反应,开发了一种高效的钯催化 1,2-二氢喹啉合成方法。这种新的 Pd(0)催化准级联型 I 序列涉及 Buchwald-Hartwig 芳基胺化和烯丙基胺化。当从邻溴烯丙醇开始时,反应历程是芳基胺化/烯丙基芳基化。然而,当反应在相应的邻溴烯丙基醋酸盐上进行时,反应顺序会反转。

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