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 | |
| Publication status | Published - Jan 29 2014 |
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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 journal › Article
}
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 -