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 › peer-review

22 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

Keywords

Alkyne
Amino
Boronic ester
Cross-coupling
Silatrane

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Organosilatrane building blocks",

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.",

keywords = "Alkyne, Amino, Boronic ester, Cross-coupling, Silatrane",

author = "Brennan, {Bradley J.} and Devens Gust and Brudvig, {Gary W.}",

note = "Funding Information: We would like to thank the Yale West Campus Analytical Core staff for help with instrumentation. This work was funded grants from the U.S. Department of Energy ( DE-FG02-07ER15909 and DE-FG02-03ER15393 ), and a generous grant from Tom Steyer and Kathryn Taylor. Copyright: Copyright 2014 Elsevier B.V., All rights reserved.",

year = "2014",

month = jan,

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doi = "10.1016/j.tetlet.2013.12.082",

language = "English",

volume = "55",

pages = "1062--1064",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Organosilatrane building blocks

AU - Brennan, Bradley J.

AU - Gust, Devens

AU - Brudvig, Gary W.

N1 - Funding Information: We would like to thank the Yale West Campus Analytical Core staff for help with instrumentation. This work was funded grants from the U.S. Department of Energy ( DE-FG02-07ER15909 and DE-FG02-03ER15393 ), and a generous grant from Tom Steyer and Kathryn Taylor. Copyright: Copyright 2014 Elsevier B.V., All rights reserved.

PY - 2014/1/29

Y1 - 2014/1/29

N2 - 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.

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.

KW - Alkyne

KW - Amino

KW - Boronic ester

KW - Cross-coupling

KW - Silatrane

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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