Advanced Synthesis & Catalysis

Palladium??Catalyzed Fluoride??Free Cross??Coupling of Intramolecularly Activated Alkenylsilanes and Alkenylgermanes: Synthesis of Tamoxifen as a Synthetic …

K Matsumoto, M Shindo

Index: Matsumoto, Kenji; Shindo, Mitsuru Advanced Synthesis and Catalysis, 2012 , vol. 354, # 4 p. 642 - 650

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Citation Number: 12

Abstract

Abstract We have demonstrated that intramolecular hypercoordination of a carboxylic acid is a powerful activation strategy for the palladium-catalyzed cross-coupling reaction of trialkyl (vinyl) silanes and trialkyl (vinyl) germanes under fluoride-free conditions. Z-β-Trialkylsilyl- and Z-β-trialkylgermylacrylic acids, synthesized stereoselectively by olefination with ynolates, are highly stable and useful reagents for cross-coupling with a variety of aryl ...

~94%

~99%

~82%

~34%

~70%

~88%

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