Direct Carbon-Carbon Bond Formation from Alcohols and Active Methylenes, Alkoxyketones, or Indoles Catalyzed by Indium Trichloride

The unsalted variety: The direct coupling reaction of alcohols with active methylenes, alkoxyketones, or indoles catalyzed by InCl3 proceeds without the formation of metal salts (see scheme). As H2O is the only by‐product of this system, the alkylated products are easily isolated in pure form, and t...

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Published inAngewandte Chemie International Edition Vol. 45; no. 5; pp. 793 - 796
Main Authors Yasuda, Makoto, Somyo, Toshio, Baba, Akio
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 23.01.2006
WILEY‐VCH Verlag
Wiley
Subjects
alcohols
Alcohols - chemistry
Carbon - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
CC coupling
indium
Indium - chemistry
Indoles - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
synthetic methods
C-C coupling
SYSTEM
PALLADIUM
SUBSTITUTION
ALKYLATION
COMPLEXES
indium
alcohols
REGIOSELECTIVITY
TRIETHYLBORANE
NUCLEOPHILES
ALLYL ALCOHOLS
synthetic methods
WATER
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Summary:The unsalted variety: The direct coupling reaction of alcohols with active methylenes, alkoxyketones, or indoles catalyzed by InCl3 proceeds without the formation of metal salts (see scheme). As H2O is the only by‐product of this system, the alkylated products are easily isolated in pure form, and the reaction is suitable for large‐scale synthesis.
Bibliography:ArticleID:ANIE200503263
This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan, and the Sumitomo Foundation. Thanks are due to Mr. H. Moriguchi, Faculty of Engineering, Osaka University, for assistance in obtaining mass spectra.
istex:277CEF21749AC6189EA8E082A35058B8DBB09078
ark:/67375/WNG-BQBVJS15-7
This work was supported by a Grant‐in‐Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan, and the Sumitomo Foundation. Thanks are due to Mr. H. Moriguchi, Faculty of Engineering, Osaka University, for assistance in obtaining mass spectra.
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200503263