Two Types of Cross-Coupling Reactions between Electron-Rich and Electron-Deficient Alkenes Assisted by Nucleophilic Addition Using an Organic Photoredox Catalyst

Two types of photoreactions between electronically differentiated donor and acceptor alkenes assisted by nucleophilic addition using an organic photoredox catalyst efficiently afforded 1:1 or 2:1 cross-coupling adducts. A variety of alkenes and alcohols were employed in the photoreaction. Control of...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 83; no. 22; pp. 13625 - 13635
Main Authors Tanaka, Yosuke, Kubosaki, Suzuka, Osaka, Kazuyuki, Yamawaki, Mugen, Morita, Toshio, Yoshimi, Yasuharu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.11.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHOTOCHEMICAL NUCLEOPHILE
CYCLOADDITION
RING EXPANSION
RADICAL-CATION
OLEFIN COMBINATION
ALIPHATIC CARBOXYLIC-ACIDS
PHOTOSUBSTITUTION
AROMATIC-SUBSTITUTION REACTION
VINYL ETHERS
PHOTOCYCLODIMERIZATION
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Summary:Two types of photoreactions between electronically differentiated donor and acceptor alkenes assisted by nucleophilic addition using an organic photoredox catalyst efficiently afforded 1:1 or 2:1 cross-coupling adducts. A variety of alkenes and alcohols were employed in the photoreaction. Control of the reaction pathway (i.e., the formation of the 1:1 or 2:1 adduct) was achieved by varying the concentration of the alcohol used. Detailed mechanistic studies suggested that the organic photoredox catalyst acts as an effective electron mediator to promote the formation of the cross-coupling adducts.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02025