Cross-coupling of aromatic bromides with allylic silanolate salts

SE Denmark, NS Werner

Index: Denmark, Scott E.; Werner, Nathan S. Journal of the American Chemical Society, 2008 , vol. 130, # 48 p. 16382 - 16393

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Citation Number: 62

Abstract

The sodium salts of allyldimethylsilanol and 2-butenyldimethylsilanol undergo palladium- catalyzed cross-coupling with a wide variety of aryl bromides to afford allylated and crotylated arenes. The coupling of both silanolates required extensive optimization to deliver the expected products in high yields. The reaction of the allyldimethylsilanolate takes place at 85° C in 1, 2-dimethoxyethane with allylpalladium chloride dimer (2.5 mol%) to afford ...