Previously, the Kishi group reported a method for a mild preparation of vinyliodides from vinylsilanes using N-iodosuccinimide (NIS) and a 9:1 mixture of acetonitrile and chloroacetonitrile as the solvent.(14) A high stereoselectivity was observed with many substrates, but simple vinylsilanes gave a mixture of products with modest stereocontrol. For example, (E)-1-trimethylsilyl-1-octene and (Z)-1-trimethylsilyl-1-octene provided mixtures of the corresponding (E)- and (Z)- ...
