Regio- and Stereoselective Synthesis of Enol Carboxylate, Phosphate, and Sulfonate Esters via Iodo(III)functionalization of Alkynes
Chang‐Sheng Wang, P. S. Tan, Wei Ding, Shingo Ito, Naohiko Yoshikai
Abstract
β-Iodo(III)enol carboxylates, phosphates, and tosylates can be efficiently synthesized through regio- and stereoselective iodo(III)functionalization of alkynes. The combination of chlorobenziodoxole and silver salt has proven to generate a versatile cationic iodine(III) electrophile to activate alkynes and engage various carboxylic acids, triethyl phosphate, and p-toluenesulfonic acid as nucleophiles. The β-iodo(III)enol esters serve as starting materials for the synthesis of multisubstituted alkenes through sequential cross-coupling of the C–I(III) and C–O bonds.
Topics & Concepts
ChemistryStereoselectivitySurface modificationEnolSulfonateCarboxylatePhosphateOrganic chemistryCombinatorial chemistryCatalysisSodiumPhysical chemistryCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesOxidative Organic Chemistry Reactions