Regio- and Stereoselective Hydroiodination of Internal Alkynes with <i>Ex Situ</i>-Generated HI

Abstract

Herein, we report an efficient and practical hydroiodination of internal alkynes using HI generated <i>ex situ</i> from the readily available triethylsilane and I₂. This system offers high regio- and stereoselectivity to afford (<i>E</i>)-vinyl iodides in good yields under mild conditions. Furthermore, the hydroiodination reaction shows high functional group tolerance toward alkyl, methoxy, halogen, trifluoromethyl, cyano, ester, halomethyl, acid-sensitive silyl ether, and acetal moieties.