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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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
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Language:English
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Ethers
Levulinic Acids
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cited_by cdi_FETCH-LOGICAL-a430t-cb8cef33b4ef485029acd28309b32e1f6c7473bcd46f4482c6c9c36ff1501a263
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container_end_page 15138
container_issue 22
container_start_page 15129
container_title Journal of organic chemistry
container_volume 87
creator Chen, Yu
Hee, Samual
Liu, Xiaochen
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Li, Jiaming
Liu, Jianbo
description 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.
doi_str_mv 10.1021/acs.joc.2c01638
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Ethers
Levulinic Acids
title ICl-Mediated Functional Group Interconversion from Methyl Homopropargyl Ether to α‑Iodo-γ-chloroketone
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