Organosilatrane building blocks

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

Research output: Contribution to journalArticle

19 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 languageEnglish
Pages (from-to)1062-1064
Number of pages3
JournalTetrahedron Letters
Volume55
Issue number5
DOIs
Publication statusPublished - Jan 29 2014

Fingerprint

Palladium
Functional groups
Esters
Silica Gel
Catalysis
Purification
Molecules
silatrane

Keywords

  • Alkyne
  • Amino
  • Boronic ester
  • Cross-coupling
  • Silatrane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Organosilatrane building blocks. / Brennan, Bradley J.; Gust, Devens; Brudvig, Gary W.

In: Tetrahedron Letters, Vol. 55, No. 5, 29.01.2014, p. 1062-1064.

Research output: Contribution to journalArticle

Brennan, Bradley J. ; Gust, Devens ; Brudvig, Gary W. / Organosilatrane building blocks. In: Tetrahedron Letters. 2014 ; Vol. 55, No. 5. pp. 1062-1064.
@article{acbce1bab05d478e924cd1aa181f40d8,
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.}",
year = "2014",
month = "1",
day = "29",
doi = "10.1016/j.tetlet.2013.12.082",
language = "English",
volume = "55",
pages = "1062--1064",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "5",

}

TY - JOUR

T1 - Organosilatrane building blocks

AU - Brennan, Bradley J.

AU - Gust, Devens

AU - Brudvig, Gary W.

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

UR - http://www.scopus.com/inward/record.url?scp=84892810869&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84892810869&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.12.082

DO - 10.1016/j.tetlet.2013.12.082

M3 - Article

VL - 55

SP - 1062

EP - 1064

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 5

ER -