Iron-Catalyzed Allylic Arylation of Olefins via C(sp3)–H Activation under Mild Conditions

An aryl Grignard reagent in the presence of mesityl iodide converts an allylic C–H bond of a cycloalkene or an allylbenzene derivative into a C–C bond in the presence of a catalytic amount of Fe(acac)3 and a diphosphine ligand at 0 °C. The stereo- and regioselectivity of the reaction, together with...

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 3; pp. 714 - 717
Main Authors Sekine, Masaki, Ilies, Laurean, Nakamura, Eiichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.02.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CROSS-COUPLING REACTIONS
ALKYLATION
IMINES
COMPLEXES
BIARYL
H BOND FUNCTIONALIZATION
GRIGNARD-REAGENTS
C-H
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Summary:An aryl Grignard reagent in the presence of mesityl iodide converts an allylic C–H bond of a cycloalkene or an allylbenzene derivative into a C–C bond in the presence of a catalytic amount of Fe(acac)3 and a diphosphine ligand at 0 °C. The stereo- and regioselectivity of the reaction, together with deuterium labeling experiments, suggest that C–H bond activation is the slow step in the catalytic cycle preceding the formation of an allyliron intermediate.
Bibliography:KAKEN
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SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol400056z