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

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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)