Reductive iodonio-Claisen rearrangement of iodothiophene diacetates with allylsilanes: formal synthesis of Plavix®

Iodothiophene diacetates react with allyltrimethylsilanes in the presence of boron trifluoride diethyl etherate to afford corresponding ortho-allyliodothiophenes via reductive iodonio-Claisen rearrangement. This method has been successfully applied to the synthesis of Plavix®, a blood clot inhibitor used to reduce the risk of heart attack and stroke.