Journal of the American Chemical Society 2014-12-31

Endo-selective Pd-catalyzed silyl methyl Heck reaction.

Marvin Parasram, Viktor O Iaroshenko, Vladimir Gevorgyan

Index: J. Am. Chem. Soc. 136(52) , 17926-9, (2014)

Full Text: HTML

Abstract

A palladium (Pd)-catalyzed endo-selective Heck reaction of iodomethylsilyl ethers of phenols and aliphatic alkenols has been developed. Mechanistic studies reveal that this silyl methyl Heck reaction operates via a hybrid Pd-radical process and that the silicon atom is crucial for the observed endo selectivity. The obtained allylic silyloxycycles were further oxidized into (Z)-alkenyldiols.