Electrophilic alkynylation of ketones using hypervalent iodine

A new method for the electrophilic α-alkynylation of ketones was developed using hypervalent iodine under mild and metal-free conditions. Carbonyl compounds containing an α-acetylene group were obtained in good to excellent yields for several ketones using 1-[(trimethylsilyl)ethynyl]-1,2-benziodoxol...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2014-01, Vol.50 (29), p.3810-3813
Main Authors: Utaka, Aline, Cavalcanti, Livia N, Silva, Jr, Luiz F
Format: Article
Language:English
Subjects:
Aldehydes
Carbonyl compounds
Iodine
Ketones
Solvents
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Summary:A new method for the electrophilic α-alkynylation of ketones was developed using hypervalent iodine under mild and metal-free conditions. Carbonyl compounds containing an α-acetylene group were obtained in good to excellent yields for several ketones using 1-[(trimethylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TMS-EBX) as an alkynylation agent in the presence of t-BuOK and TBAF in THF as solvent. Under the same conditions, an aldehyde was alkynylated.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc00608a