Skip to main content
. Author manuscript; available in PMC: 2012 Mar 21.
Published in final edited form as: Chemistry. 2011 Mar 1;17(13):3630–3643. doi: 10.1002/chem.201003454

Table 3.

Attempted elimination conditions.

graphic file with name nihms264460u4.jpg
Entry Conditions Notes
1 2 equiv. LDA, THF, −78 °C Decomposition to baseline by TLC
2 1 equiv. KOtBu, THF, 0 –40 °C No desired product
3 5 equiv. KOtBu, THF, rt Messy, t-BuO− attacked ester
4 1 eq LIDAKOR[a], hexanes, 0 °C-rt NR (substrate not dissolving)
5 1 eq LIDAKOR, THF, −78 °C Decomposition to baseline by TLC
6 1.5 eq DBU, toluene, reflux NR
7 50 mol% In(OTf)3, 2,6-di-tert-butylpyridine, THF, 50 °C NR
8 20 mol% In(OTf)3, proton-sponge, THF, reflux No desired reaction. In(OTf)3 reacted with proton-sponge to form insoluble solids in the reaction.
9 Ho(OTf)3, 2,6-di-tert-butylpyridine, chlorobenzen, 100 °C NR, recovered starting material
10 Al(OTf)3, 2,6-di-tert-butylpyridine, DCM, 0 °C-rt 100% NMR yield[c] of
graphic file with name nihms264460t1.jpg
24
11 In(OTf)3, 2,6-di-tert-butylpyridine, chlorobenzene, 100 °C NMR yields: 23% 23, 30% 24,
graphic file with name nihms264460t2.jpg
25
30%
12 In(OTf)3, 2,6-di-tert-butylpyridine, chlorobenzene, 3Å MS, 100 °C NR, recovered starting material
[a]

LIDAKOR=LDA + tBuOK.

[b]

NR = no reaction

[c]

NMR yields were determined by using 1,3,5-trimethoxybenzene as an internal standard.