Synthesis of various silacycles via the Lewis acid-catalyzed intramolecular trans-hydrosilylation of unactivated alkynes

T. Sudo; N. Asao; Y. Yamamoto

doi:10.1021/jo000670n

Synthesis of various silacycles via the Lewis acid-catalyzed intramolecular trans-hydrosilylation of unactivated alkynes

T. Sudo, N. Asao, Y. Yamamoto

Research output: Contribution to journal › Article › peer-review

69 Citations (Scopus)

Abstract

Various silacycles with vinylsilane framework are synthesized via the Lewis acid-catalyzed intramolecular hydrosilylation of alkynes. The cyclization proceeds in an endo-trans or/and in an exo-trans manner, depending on the substrate structure. This methodology is applicable to the synthesis of five-, six-, seven-, and eight-membered medium-sized silacycles. Furthermore, it is possible to obtain a silole derivative via the intramolecular hydrosilylation of the ortho-alkynyl-substituted phenylsilane 10.

Original language	English
Pages (from-to)	8919-8923
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	65
Issue number	26
DOIs	https://doi.org/10.1021/jo000670n
Publication status	Published - 2000 Dec 29

ASJC Scopus subject areas

Organic Chemistry

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title = "Synthesis of various silacycles via the Lewis acid-catalyzed intramolecular trans-hydrosilylation of unactivated alkynes",

abstract = "Various silacycles with vinylsilane framework are synthesized via the Lewis acid-catalyzed intramolecular hydrosilylation of alkynes. The cyclization proceeds in an endo-trans or/and in an exo-trans manner, depending on the substrate structure. This methodology is applicable to the synthesis of five-, six-, seven-, and eight-membered medium-sized silacycles. Furthermore, it is possible to obtain a silole derivative via the intramolecular hydrosilylation of the ortho-alkynyl-substituted phenylsilane 10.",

author = "T. Sudo and N. Asao and Y. Yamamoto",

year = "2000",

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T1 - Synthesis of various silacycles via the Lewis acid-catalyzed intramolecular trans-hydrosilylation of unactivated alkynes

AU - Sudo, T.

AU - Asao, N.

AU - Yamamoto, Y.

PY - 2000/12/29

Y1 - 2000/12/29

N2 - Various silacycles with vinylsilane framework are synthesized via the Lewis acid-catalyzed intramolecular hydrosilylation of alkynes. The cyclization proceeds in an endo-trans or/and in an exo-trans manner, depending on the substrate structure. This methodology is applicable to the synthesis of five-, six-, seven-, and eight-membered medium-sized silacycles. Furthermore, it is possible to obtain a silole derivative via the intramolecular hydrosilylation of the ortho-alkynyl-substituted phenylsilane 10.

AB - Various silacycles with vinylsilane framework are synthesized via the Lewis acid-catalyzed intramolecular hydrosilylation of alkynes. The cyclization proceeds in an endo-trans or/and in an exo-trans manner, depending on the substrate structure. This methodology is applicable to the synthesis of five-, six-, seven-, and eight-membered medium-sized silacycles. Furthermore, it is possible to obtain a silole derivative via the intramolecular hydrosilylation of the ortho-alkynyl-substituted phenylsilane 10.

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