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

Represented is a CuX2- or I-2-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 = CI, 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.

Automated summary

The method described involves a ring-opening dual halogenation of cyclopropenones with saturated oxygen heterocycles, catalyzed by CuX2 or I-2, providing an efficient synthesis route for 3-haloacrylates. This protocol is highly atom economical, exhibits excellent substrate scope, and can be scaled up for gram-scale reactions.