Regio- and Stereoselective Generation of Alkenylindium Compounds from Indium Tribromide, Alkynes, and Ketene Silyl Acetals

InBr₃ promotes the addition of ketene silyl acetals to monosubstituted alkynes to afford 2,2-disubstituted alkenylindium compounds in high regio- and stereoselectivity (see scheme). In addition, the alkenylindium derivatives have been subsequently coupled with iodobenzene in the presence of a pallad...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 48; no. 25; pp. 4577 - 4580
Main Authors Nishimoto, Yoshihiro, Moritoh, Ryosuke, Yasuda, Makoto, Baba, Akio
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2009
WILEY‐VCH Verlag
Wiley
Subjects
alkynes
carboindation
Chemistry
Chemistry, Multidisciplinary
indium
ketene silyl acetals
Physical Sciences
Science & Technology
synthetic methods
carboindation
ENOL ETHERS
alkynes
ALLYLATION
indium
TERMINAL ALKYNES
INTRAMOLECULAR TRANS-VINYLSILYLATION
FRIEDEL-CRAFTS ALKENYLATION
UNACTIVATED ALKYNES
ketene silyl acetals
FUNCTIONALIZED ALKYNES
CARBON TRIPLE BONDS
synthetic methods
CYCLIZATION
Online AccessGet full text

Cover

More Information
Summary:InBr₃ promotes the addition of ketene silyl acetals to monosubstituted alkynes to afford 2,2-disubstituted alkenylindium compounds in high regio- and stereoselectivity (see scheme). In addition, the alkenylindium derivatives have been subsequently coupled with iodobenzene in the presence of a palladium catalyst.
Bibliography:http://dx.doi.org/10.1002/anie.200901417
This work was supported by a Grant‐in‐Aid for Scientific Research on Priority Areas (grant no. 18065015, “Chemistry of Concerto Catalysis” and grant no. 20036036, “Synergistic Effects for Creation of Functional Molecules”) and for Scientific Research (grant no. 19550038) from the Ministry of Education, Culture, Sports, Science and Technology (Japan). We thank Dr. Nobuko Kanehisa for the valuable advice regarding X‐ray crystallography. Y. N. thanks The Global COE Program “Global Education and Research Center for Bio‐Environment Chemistry” of Osaka University.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200901417