Visible-light-promoted divergent functionalizations of methylenecyclopropanes

Simple and convenient visible-light-promoted radical monofunctionalization and difunctionalization of methylenecyclopropanes via ring-opening and cyclization processes have been developed for the syntheses of difluoromethyl compounds, alkyl compounds, halides, and sulfonyl compounds in moderate to e...

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Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 8; no. 22; pp. 6300 - 6308
Main Authors Zhu, Baoxiang, Wang, Zhao, Xi, Hui, Feng, Zengqiang, Wang, Binglei, Jiao, Wenyang, Li, Zhongxian, Wang, Zechao, Wu, Junliang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 09.11.2021
Royal Society of Chemistry
Subjects
Alkyl compounds
Chemistry
Chemistry, Organic
Electron transfer
Functional groups
Halides
Organic chemistry
Physical Sciences
Ring opening
Science & Technology
Single electrons
Substrates
ACID-MEDIATED CYCLOADDITION
METAL-CATALYZED REACTIONS
FACILE SYNTHESIS
RING EXPANSION
ALKYLIDENECYCLOPROPANES
LEWIS
HYDROAMINATION
BOND-CLEAVAGE
CYCLOPROPENE
PYRROLIDINE SKELETONS
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Summary:Simple and convenient visible-light-promoted radical monofunctionalization and difunctionalization of methylenecyclopropanes via ring-opening and cyclization processes have been developed for the syntheses of difluoromethyl compounds, alkyl compounds, halides, and sulfonyl compounds in moderate to excellent yields. The methodologies feature a wide substrate scope and tolerate various functional groups. A possible radical mechanism has been investigated and proven as a single electron transfer (SET) procedure.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d1qo01187a