Photoredox Synthesis of Thio‐Functionalized Cyclic Ethers Using N‐Sulfenyl Phthalimides as a Thiyl‐Radical Precursor

Comprehensive Summary A visible‐light mediated exclusively regioselective synthesis of 2,2‐disubstituted thio‐functionalized tetrahydrofurans, tetrahydro‐ pyrans and oxepanes has been described through an operationally simple and mild photoredox protocol. Thiyl radical generated from N‐phenylsulfeny...

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Published in:Chinese journal of chemistry 2023-08, Vol.41 (15), p.1823-1828
Main Authors: Lu, Maojian, Liang, Rong‐Bin, Zhu, Can‐Ming, Tong, Qing‐Xiao, Zhong, Jian‐Ji
Format: Article
Language:English
Subjects:
Catalysis
Cyclic ethers
Cycloaddition
Ethers
N‐Sulfenyl phthalimides
Photoredox catalysis
Phthalimide
Phthalimides
Reaction mechanisms
Sulfenylating reagent
Synthesis
Synthetic methods
Thio‐functionalization
Thiyl radical
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cited_by cdi_FETCH-LOGICAL-c3178-a407c671dc9f44308123f623d161c434cae07ed1da9dd07d4cc7fc9b7b04bac53
cites cdi_FETCH-LOGICAL-c3178-a407c671dc9f44308123f623d161c434cae07ed1da9dd07d4cc7fc9b7b04bac53
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container_issue 15
container_start_page 1823
container_title Chinese journal of chemistry
container_volume 41
creator Lu, Maojian
Liang, Rong‐Bin
Zhu, Can‐Ming
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Zhong, Jian‐Ji
description Comprehensive Summary A visible‐light mediated exclusively regioselective synthesis of 2,2‐disubstituted thio‐functionalized tetrahydrofurans, tetrahydro‐ pyrans and oxepanes has been described through an operationally simple and mild photoredox protocol. Thiyl radical generated from N‐phenylsulfenyl phthalimide by photoredox catalysis was proven to be the key reactive intermediate in this reaction. A simple and mild photocatalytic approach was reported to realize a metal‐free synthesis of 2,2‐disubstituted thio‐functionalized tetrahydrofurans, tetrahydropyrans and oxepanes with high regioselectivity using N‐phenylsulfenyl phthalimide, a commonly used electrophile sulfenylating reagent, as a radical precursor.
doi_str_mv 10.1002/cjoc.202300118
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ispartof Chinese journal of chemistry, 2023-08, Vol.41 (15), p.1823-1828
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subjects Catalysis
Cyclic ethers
Cycloaddition
Ethers
N‐Sulfenyl phthalimides
Photoredox catalysis
Phthalimide
Phthalimides
Reaction mechanisms
Sulfenylating reagent
Synthesis
Synthetic methods
Thio‐functionalization
Thiyl radical
title Photoredox Synthesis of Thio‐Functionalized Cyclic Ethers Using N‐Sulfenyl Phthalimides as a Thiyl‐Radical Precursor
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