Generation of a small library of highly electron-rich 2-(Hetero)aryl-substituted phenethylamines by the Suzuki-Miyaura reaction: A short synthesis of an apogalanthamine analogue

被引：41
作者：
Appukkuttan, P
Orts, AB
Chandran, RP
Goeman, JL
Van der Eycken, J
Dehaen, W
Van der Eycken, E
机构：
[1] Univ Louvain, Organ Synth Lab, B-3001 Louvain, Belgium
[2] Univ Ghent, Lab Organ & Bioorgan Synth, B-9000 Ghent, Belgium
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 15期
关键词：
apogalanthamine; biaryls; cross coupling; microwave irradiation; palladium;
D O I：
10.1002/ejoc.200400213
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Suzuki-Miyaura reaction is presented as a versatile procedure for the synthesis of a small library of highly electron-rich 2-[4,5-dimethoxy-2-(hetero)arylphenyl]ethylamines. Microwave-irradiation accelerates the reaction tremendously and furnishes superior yields. The difficult oxidative addition of the catalyst to a highly electron-rich and ortho-substituted system could be performed easily, and the proto-deboronation during cross-coupling reactions involving the highly electron-withdrawing (2-formylphenyl)boronic acid could be minimized. Enhanced yields and complete compatibility with aqueous conditions were found. This strategy was developed en route towards the synthesis of an apogalanthamine analogue. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
引用
收藏
页码：3277 / 3285
页数：9
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