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Synlett 2010(18): 2743-2746  
DOI: 10.1055/s-0030-1258816
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Hydrosilylation-Metathesis Sequence Leading to 1-Silaindenes

Takanori Matsuda*,, Yoshiyuki Yamaguchi, Naoki Ishida, Masahiro Murakami*
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan
Fax: +81(75)3832752; e-Mail: murakami@sbchem.kyoto-u.ac.jp;
Further Information

Publication History

Received 25 August 2010
Publication Date:
08 October 2010 (online)

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Abstract

1-Silaindenes are prepared starting from (2-vinylphenyl)hydrosilanes and alkynes through a ruthenium-catalyzed hydrosilylation-ring-closing-metathesis sequence. The method is successfully applied to the synthesis of molecules containing multiple silaindene units.

Key words

hydrosilylation - metathesis - ruthenium - homogeneous catalysis - ring closure

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1

Present address: Department of Applied Chemistry, Tokyo University of Science, Shinjuku, Tokyo 162-8601, Japan.

9

The regioselectivity of the trans-hydrosilylation was so high that other isomers were scarcely found in the crude reaction mixtures.

10

Replacement of the dimethylsilylene (-SiMe2-) moiety of 1a with diethylsilylene (-SiEt2-) moiety significantly retarded the hydrosilylation (6%) due to severe steric congestion around the silicon.