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Cascade Ring-Opening Dual Halogenation of Cyclopropenones with Saturated Oxygen Heterocycles

Weihang Miao, Wenxia Gao, Xiaobo Huang, Miaochang Liu, Yunbing Zhou, Huayue Wu

2021Organic Letters19 citationsDOI

Abstract

-promoted ring-opening dual halogenation of cyclopropenones with saturated oxygen heterocycles, providing an efficient method for the synthesis of 3-haloacrylates. The ring-opening reaction enables the construction of two C-X (X = Cl, Br, or I) bonds and a C-O bond as well as the cleavage of two C-O bonds and a C-C bond in a single step. This protocol is highly atom economical, has an excellent substrate scope, and exhibits the ability for gram-scale reaction.

Topics & Concepts

HalogenationChemistryRing (chemistry)Bond cleavageCascadeSubstrate (aquarium)Oxygen atomOxygenCleavage (geology)Combinatorial chemistryMedicinal chemistryMoleculeOrganic chemistryCatalysisEngineeringOceanographyGeotechnical engineeringGeologyChromatographyFracture (geology)Cyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions
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