Regio- and Stereoselective Hydroiodination of Internal Alkynes with <i>Ex Situ</i>-Generated HI
Kanako Nozawa‐Kumada, K. Noguchi, Tomoya Akada, Masanori Shigeno, Yoshinori Kondo
Abstract
Herein, we report an efficient and practical hydroiodination of internal alkynes using HI generated ex situ from the readily available triethylsilane and I2. This system offers high regio- and stereoselectivity to afford (E)-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.
Topics & Concepts
ChemistryStereoselectivityTriethylsilaneSilyl etherTrifluoromethylEtherIn situHalogenSilylationAlkylAcetalStereochemistryMedicinal chemistryOrganic chemistryCatalysisCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesVanadium and Halogenation Chemistry