ICl-Mediated Functional Group Interconversion from Methyl Homopropargyl Ether to α‑Iodo-γ-chloroketone

An ICl-mediated highly chemo- and regioselective functional group interconversion from methyl homopropargyl ether to α-iodo-γ-chloro-ketone is reported. Density functional theory (DFT)-calculated reaction coordinate and potential energy surface support the high chemo-selectivity observed for the for...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-11, Vol.87 (22), p.15129-15138
Main Authors: Chen, Yu, Hee, Samual, Liu, Xiaochen, Das, Sajal, Hong, Dongsub, Leung, Pak-Hing, Li, Yongxin, Li, Jiaming, Liu, Jianbo
Format: Article
Language:English
Subjects:
Ethers
Levulinic Acids
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Summary:An ICl-mediated highly chemo- and regioselective functional group interconversion from methyl homopropargyl ether to α-iodo-γ-chloro-ketone is reported. Density functional theory (DFT)-calculated reaction coordinate and potential energy surface support the high chemo-selectivity observed for the formation of α-iodo-γ-chloroketone over furan. The five-membered oxonium ring formation–ring opening mechanism is a potential template for the preparation of polyfunctionalized carbonyl compounds.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01638