Abstract
Although Grubbs metathesis catalysts have enabled syntheses of a range of molecules, alkene isomerization, a known and problematic side reaction, is poorly understood. Several mechanisms which have been advanced to account for isomerization were studied by using electronic structure calculations. The pathway catalyzed by a ruthenium hydride emerged as the most facile process by a significant margin. For the first time, we have obtained experimental evidence for the presence of this species in a metathesis-active system.
| Language | English |
|---|---|
| Pages | 5673–5677 |
| Number of pages | 5 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2012 |
| Issue number | 29 |
| DOIs | |
| Publication status | Published - Oct 2012 |
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Keywords
- ruthenium
- metathesis
- homogeneous catalysis
- density functional calculations
- kinetics
Cite this
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Searching for the hidden hydrides : the competition between alkene isomerization and metathesis with Grubbs catalysts. / Ashworth, Ian W.; Hillier, Ian H.; Nelson, David J; Percy, Jonathan M; Vincent, Mark A.
In: European Journal of Organic Chemistry, Vol. 2012, No. 29, 10.2012, p. 5673–5677.Research output: Contribution to journal › Article
TY - JOUR
T1 - Searching for the hidden hydrides
T2 - European Journal of Organic Chemistry
AU - Ashworth, Ian W.
AU - Hillier, Ian H.
AU - Nelson, David J
AU - Percy, Jonathan M
AU - Vincent, Mark A.
PY - 2012/10
Y1 - 2012/10
N2 - Although Grubbs metathesis catalysts have enabled syntheses of a range of molecules, alkene isomerization, a known and problematic side reaction, is poorly understood. Several mechanisms which have been advanced to account for isomerization were studied by using electronic structure calculations. The pathway catalyzed by a ruthenium hydride emerged as the most facile process by a significant margin. For the first time, we have obtained experimental evidence for the presence of this species in a metathesis-active system.
AB - Although Grubbs metathesis catalysts have enabled syntheses of a range of molecules, alkene isomerization, a known and problematic side reaction, is poorly understood. Several mechanisms which have been advanced to account for isomerization were studied by using electronic structure calculations. The pathway catalyzed by a ruthenium hydride emerged as the most facile process by a significant margin. For the first time, we have obtained experimental evidence for the presence of this species in a metathesis-active system.
KW - ruthenium
KW - metathesis
KW - homogeneous catalysis
KW - density functional calculations
KW - kinetics
UR - http://www.scopus.com/inward/record.url?scp=84866893196&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201201036
DO - 10.1002/ejoc.201201036
M3 - Article
VL - 2012
SP - 5673
EP - 5677
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 29
ER -