Oxidative Umpolung α‑Alkylation of Ketones

We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 2; pp. 282 - 285
Main Authors Shneider, O. Svetlana, Pisarevsky, Evgeni, Fristrup, Peter, Szpilman, Alex M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.01.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYSIS
ALKENES
ARYLATION
TOSYLOXYLATION
CHEMISTRY
SALTS
TRIFLUOROMETHYLATION
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Summary:We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol503384c