Table 7.
Entry |
Catalyst [mol %] |
t [h] |
Conv. [%][b] |
Selectivity trans‐3 [%] |
trans/ cis 3 |
---|---|---|---|---|---|
1 |
A (2)+[Bu4N]Br (3) |
4.5 |
68 |
76 |
1:0 |
2 |
A (1)+[Bu4N]Br (3) |
4.5 |
56 |
77 |
1:0 |
3 |
A (1)+[Bu4N]Br (3) |
24 |
91 |
64 |
1:0 |
4 |
A (5) |
4.5 |
83 |
72 |
1:0 |
5 |
[Bu4N]Cl (3) |
4.5 |
35 |
82 |
1:0 |
6 |
[Bu4N]Br (3) |
4.5 |
45 |
59 |
1:0 |
7 |
[Bu4N]I (3) |
4.5 |
15 |
52 |
1:0 |
8 |
Aliquat 336[c] (3) |
4.5 |
34 |
69 |
1:0 |
9 |
A (2)+[Bu4N]Cl (3) |
4.5 |
83 |
78 |
1:0 |
10 |
A (2)+[Bu4N]I (3) |
4.5 |
55 |
39 |
1:0 |
11 |
A (2)+[Bu4N]Cl (3) |
24 |
93 |
74 |
1:0 |
12 |
A (2)+[Bu4N]Br (3) |
24 |
96 |
55 |
1:0 |
13 |
A (2)+[Bu4N]I (3) |
24 |
98 |
67 |
1:0 |
14 |
none |
4.5 |
–[d] |
– |
– |
[a] Reaction conditions: trans‐2 (2.0—2.6 mmol) (see the Supporting Information IVc), 140 °C, 75 bar CO2 at 40 °C, biphenyl (10 mol %) as an internal standard, stirrer speed 300 rpm. [b] Determined from quantitative 1H NMR spectroscopy. [c] Aliquat 336=commercial mixture of C8 and C10 quaternary ammonium salts with predominately N‐methyl‐N,N,N‐trioctylammonium chloride. [d] 5 % mass loss.