Nickel-Catalyzed Three-Component Coupling between Aryl Aldehydes, Norbornenes, and Silanes Leading to Indanols through Aromatic CH Bond Activation of Aryl Aldehydes

The first example of the title reaction involving the combination of an aryl aldehyde, norbornene, and silane has been developed (see scheme). The reaction involves aromatic CH bond activation of an aryl aldehyde at the ortho position, it proceeded with good diastereoselectively, and is applicable...

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Published inAngewandte Chemie International Edition Vol. 50; no. 26; pp. 5896 - 5899
Main Authors Ogata, Kenichi, Atsuumi, Yuka, Shimada, Daisuke, Fukuzawa, Shin-ichi
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 20.06.2011
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
cycloalkenes
CH activation
indanols
nickel
Physical Sciences
Science & Technology
synthetic methods
nickel
ALKENES
indanols
C-H activation
cycloalkenes
ALKYNES
synthetic methods
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Summary:The first example of the title reaction involving the combination of an aryl aldehyde, norbornene, and silane has been developed (see scheme). The reaction involves aromatic CH bond activation of an aryl aldehyde at the ortho position, it proceeded with good diastereoselectively, and is applicable for various aryl aldehydes and norbornenes or norbornadienes. cod=cycloocta‐l,5‐diene, THF=tetrahydrofuran, NHC=N‐heterocyclic carbene.
Bibliography:This work was financially supported by a Joint Research Grant from the Institute of Science and Engineering, Chuo University. We are grateful to Prof. Ken Tanaka (Tokyo University of Agriculture and Technology) for obtaining HRMS spectrometric data for some compounds.
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ArticleID:ANIE201101468
Institute of Science and Engineering, Chuo University
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201101468