Generation of (E)-beta-sulfonyl enamines from sulfur dioxide via a radical process

An iron(ii)-catalyzed three-component reaction of O-acyl oximes, sulfur dioxide, and N-vinylacetamides is accomplished. Diverse (E)-beta-sulfonyl enamines are obtained in moderate to good yields by using this protocol with excellent stereoselectivity and regioselectivity under mild conditions. Vario...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 8; no. 8; pp. 1789 - 1794
Main Authors Tu, Xiaodong, Huang, Jiapian, Xie, Wenlin, Zhu, Tonghao, Wu, Jie
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.04.2021
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Covalent bonds
Functional groups
Information processing
Iron
NMR
Nuclear magnetic resonance
Organic chemistry
Oximes
Physical Sciences
Regioselectivity
Ring opening
Science & Technology
Stereoselectivity
Sulfur
Sulfur dioxide
SODIUM METABISULFITE
CINNAMIC-ACIDS
INSERTION
HYDROGENATION
VINYL SULFONES
HETEROCYCLES
BOND FORMATION
CYANOALKYL
INHIBITORS
PHOTOREDOX-CATALYZED SULFONYLATION
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Summary:An iron(ii)-catalyzed three-component reaction of O-acyl oximes, sulfur dioxide, and N-vinylacetamides is accomplished. Diverse (E)-beta-sulfonyl enamines are obtained in moderate to good yields by using this protocol with excellent stereoselectivity and regioselectivity under mild conditions. Various sensitive functional groups are compatible, and a broad reaction scope is presented. A plausible mechanism is proposed, which undergoes a radical pathway through a alpha-carbon radical intermediate generated from iron-catalyzed ring-opening C-C bond cleavage of O-acyl oxime.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d0qo01551b