Radical Ring-Opening Fluorosulfonylation of Methylenecyclobutanols via Electron Donor–Acceptor Photoactivation

Radical Ring-Opening Fluorosulfonylation of Methylenecyclobutanols via Electron Donor–Acceptor Photoactivation

A visible-light-mediated catalyst- and additive-free method for radical ring-opening fluorosulfonylation of methylenecyclobutanols is reported. Sulfuryl chlorofluoride acts as a FSO2 radical precursor as well as an electron acceptor to form electron donor–acceptor complexes with various methylenecyc...

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Veröffentlicht in:Organic letters 2024-07, Vol.26 (26), p.5577-5581
Hauptverfasser: He, Tianyu, Liang, Chaoqiang, Jiang, Ping, Liang, Hui, Liao, Saihu, Huang, Shenlin
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electrons
methodology
regioselectivity
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container_end_page 5581
container_issue 26
container_start_page 5577
container_title Organic letters
container_volume 26
creator He, Tianyu
Liang, Chaoqiang
Jiang, Ping
Liang, Hui
Liao, Saihu
Huang, Shenlin
description A visible-light-mediated catalyst- and additive-free method for radical ring-opening fluorosulfonylation of methylenecyclobutanols is reported. Sulfuryl chlorofluoride acts as a FSO2 radical precursor as well as an electron acceptor to form electron donor–acceptor complexes with various methylenecyclobutanol substrates. This method shows fully regioselective and (E)-stereoselective ring-opening processes, providing a variety of FSO2-functionalized γ,δ-unsaturated carbonyls in 38–77% yields. A selection of product diversifications has been studied to demonstrate the versatility of these sulfonyl fluoride products.
doi_str_mv 10.1021/acs.orglett.4c01989
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subjects electrons
methodology
regioselectivity
title Radical Ring-Opening Fluorosulfonylation of Methylenecyclobutanols via Electron Donor–Acceptor Photoactivation
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