Organosilatrane building blocks

Bradley J. Brennan; Devens Gust; Gary W. Brudvig

doi:10.1016/j.tetlet.2013.12.082

Organosilatrane building blocks

Bradley J. Brennan, Devens Gust, Gary W. Brudvig

Research output: Contribution to journal › Article

21 Citations (Scopus)

Abstract

Phenylsilatrane analogues containing reactive amino, bromo, boronic ester, and alkynyl functional groups for coupling reactions have been prepared. Pinacol boronic ester and ethynyl analogues were synthesized from 4- bromophenylsilatrane by palladium catalyzed reactions. The silatrane functional group was shown to be stable during the palladium catalysis procedures and silica-gel purification, making the molecules amenable to further synthetic manipulation. The described phenylsilatranes are useful building blocks for forming more complex organosilatrane species.

Original language	English
Pages (from-to)	1062-1064
Number of pages	3
Journal	Tetrahedron Letters
Volume	55
Issue number	5
DOIs	https://doi.org/10.1016/j.tetlet.2013.12.082
Publication status	Published - Jan 29 2014

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Keywords

Alkyne
Amino
Boronic ester
Cross-coupling
Silatrane

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Brennan, B. J., Gust, D., & Brudvig, G. W. (2014). Organosilatrane building blocks. Tetrahedron Letters, 55(5), 1062-1064. https://doi.org/10.1016/j.tetlet.2013.12.082

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AB - Phenylsilatrane analogues containing reactive amino, bromo, boronic ester, and alkynyl functional groups for coupling reactions have been prepared. Pinacol boronic ester and ethynyl analogues were synthesized from 4- bromophenylsilatrane by palladium catalyzed reactions. The silatrane functional group was shown to be stable during the palladium catalysis procedures and silica-gel purification, making the molecules amenable to further synthetic manipulation. The described phenylsilatranes are useful building blocks for forming more complex organosilatrane species.

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Access to Document

10.1016/j.tetlet.2013.12.082