4.8 Article

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

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ORGANIC LETTERS
卷 23, 期 24, 页码 9425-9430

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03566

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  1. National Natural Science Foundation of China [21901187, 21472140]
  2. Natural Science Foundation of Zhejiang Province [LY21B020001]

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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.
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.

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