Ritter-type iodo( <scp>iii</scp> )amidation of unactivated alkynes for the stereoselective synthesis of multisubstituted enamides
Jinkui Chai, Wei Ding, Chen Wang, Shingo Ito, Junliang Wu, Naohiko Yoshikai
Abstract
-difunctionalization of alkynes with a trivalent iodine electrophile and nitrile, which affords β-iodanyl enamides in moderate to good yields. Mediated by benziodoxole triflate (BXT), the reaction proves applicable to a variety of internal alkynes as well as to various alkyl- and arylnitriles. The benziodoxole group in the product serves as a versatile handle for further transformations, thus allowing for the preparation of various tri- and tetrasubstituted enamides that are not readily accessible by other means.
Topics & Concepts
Ritter reactionChemistryStereoselectivityNitrileAlkeneElectrophileCarbocationOrganic chemistryCombinatorial chemistryAlcoholCatalysisAdvanced Synthetic Organic ChemistrySynthesis and Catalytic ReactionsChemical Synthesis and Analysis