Regio- and Stereoselective Iodoacyloxylations of Alkynes

A new
method for the regioselective and stereoselective iodoacyloxylation
of alkynes has been developed. This protocol utilizes a combination
of an iodobenzene dicarboxylate and iodine to functionalize a series
of activated and unactivated alkynes in an entirely selective and
predictable fashion. The resultant iodo-enol esters were subsequently
coupled with boronic acids to afford tetrasubstituted alkene derivatives,
which could be further converted to the corresponding 1,1-disubstituted
acetophenone.