Lactonization with concomitant 1,2-aryl migration and alkoxylation mediated by dialkoxyphenyl iodides generated <i>in situ</i>
Jingran Zhang, Ayesha Jalil, Jiaxin He, Zhenyang Yu, Yifu Cheng, Guangchen Li, Yunfei Du, Kang Zhao
Abstract
A series of alkoxylated isobenzofuranones were conveniently synthesized from the reaction of 2-(1-arylvinyl)benzoic acids with PhI(OR)2, generated in situ from the reaction of iodosobenzene (PhIO) with alkyl alcohols. This hypervalent iodine mediated one-pot transformation is postulated to undergo a cascade reaction involving lactonization, 1,2-aryl migration and alkoxylation processes. The organocatalytic and chiral organoiodine-catalyzed asymmetric reactions of the current transformation were also probed.
Topics & Concepts
ArylIn situAlkylChemistryTransformation (genetics)ConcomitantMedicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryBiochemistryMedicineInternal medicineGeneOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions