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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Bibliographic Details
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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Summary: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.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202300118