Hypervalent Iodine Reagents Enable C–H Alkynylation with Iminophenylacetic Acids via Alkoxyl Radicals
Zhengyi Liu, Yue Pan, Peng Zou, Hanchu Huang, Yali Chen, Yali Chen, Yiyun Chen, Yiyun Chen
Abstract
Here we report δ-C-H alkynylation to synthesize various δ-alkynols from iminophenylacetic acids. The hypervalent iodine-coordinated benziodoxole-alkoxyl-iminophenylacetic acid complex was the key intermediate and was characterized by X-ray crystallography for the first time. δ-C-H alkynylation is compatible with sensitive functional groups, including azides, aldehydes, and free alcohols, for the synthesis of δ-alkynols with diversified substituents in excellent regioselectivity. This reaction extends to δ-hydroxylalkene and δ-hydroxylnitrile synthesis, and the δ-alkynol products are easily derivatized to other valuable bifunctional building blocks.
Topics & Concepts
Hypervalent moleculeChemistryIodineReagentAlkynylationRadicalAlkoxy groupCombinatorial chemistryOrganic chemistryCatalysisAlkylOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions