Table 3.
MF isomerization to acetates: ligand and P/Pd ratio variation.[a]
Entry |
Precursor |
Additional ligand [equiv.] |
Precipitate[b] |
TON[c] |
|
---|---|---|---|---|---|
AcOMe |
AcOH |
||||
1 |
[Pd(Cl)2(dppe)] |
– |
yes |
285 |
32 |
2 |
[Pd(Cl)2(dppe)] |
1 |
no |
516 |
115 |
3 |
Pd(Cl)2(dppe) |
2 |
no |
756 |
159 |
4 |
[Pd(Cl)2(dppe)] |
4 |
no |
710 |
151 |
5 |
[Pd(Cl)2(dppm)] |
1 |
yes |
348 |
30 |
6 |
[Pd(Cl)2(dppp)] |
1 |
yes |
320 |
23 |
7 |
[Pd(Cl)2(Xantphos)] |
2 |
yes |
333 |
21 |
8 |
[Pd(Cl)2(dppf)] |
2 |
yes |
278 |
21 |
9 |
[Pd(Cl)2(dcype)] |
2 |
yes |
82 |
9 |
10 |
[Pd(Cl)2(dppmbz)] |
2 |
yes |
239 |
18 |
11 |
[Pd(Cl)2(PNPPh)] |
2 |
no |
544 |
146 |
|
|
|
|
|
|
|
[a] [Pd]=10 μmol, NaOMe=0.05 mmol, NaI=1.0 mmol, MF=4.0 mL, T=160 °C, t=15 h. Products were quantified using GC‐FID with mesitylene as internal standard. [b] Precipitate formed at the end of the reaction. [c] TON=mmolproduct mmolcatalyst −1.