Influence of the catalytic conditions on the selectivity of the Pd-catalyzed Heck arylation of acrolein derivatives

被引：23

作者：

Noel, Sebastein ^{[1
]}

Djakovitch, Laurent ^{[1
]}

Pinel, Catherine ^{[1
]}

机构：

[1] Inst Rech Catalyse, CNRS, UPR 5401, F-69626 Villeurbanne, France

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 23期

关键词：

Heck arylation; acrolein; acrolein diethyl acetal; cinnamon derivatives; aromatic compounds; heteroaromatic compounds;

D O I：

10.1016/j.tetlet.2006.03.186

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Heck arylation of acrolein with a variety of condensed aryl and heteroaryl halides is described. Depending on the substrate, up to 87% isolated yield to the expected aldehydes was achieved. When the reaction was run on diethylacetal acrolein, the choice of catalytic system dramatically affected the selectivity of the reaction: the catalyst system based on Herrmann's palla-dacycle complex gave mainly saturated esters 2, whereas Cacchi's conditions led to the formation of alpha,beta-unsaturated aldehydes 1. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3839 / 3842

页数：4

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