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Intermolecular Tandem Addition/Esterification Reaction of Alkenes with Malonates Leading to γ‐Lactones Mediated by Molecular Iodine under Visible Light Irradiation
Author(s) -
Maejima Saki,
Yamaguchi Eiji,
Itoh Akichika
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700809
Subject(s) - chemistry , intermolecular force , photochemistry , iodine , irradiation , tandem , halogenation , substrate (aquarium) , combinatorial chemistry , organic chemistry , molecule , nuclear physics , composite material , geology , physics , materials science , oceanography
The iodine‐mediated intermolecular C−C bond‐forming/esterification reaction of various alkenes including α‐olefins with malonates under irradiation using a compact fluorescent lamp has been developed to synthesize γ‐lactones in moderate to excellent yields. The method developed in this research shows broad substrate scope and moderate diastereoselectivity and constructs valuable polyfunctionalized γ‐lactones. Furthermore, the developed methodology was comprehensively studied by performing several control experiments, radical trapping, and radical clock experiments. These experiments showed that sequential iodination by an iodine radical is triggered for the following C−C bond‐forming reaction.γ