Table 1.
entry | Lewis acid (2 equiv) | silicate (equiv) | solvent | time (h) | % conva |
---|---|---|---|---|---|
1 | none | 2 | DMSO | 24 | 40 |
2 | none | 2 | DMSO | 49 | 48 |
3 | ZnBr2 | 1 | DMSO | 18 | 27 |
4 | Zn(OTf)2 | 1 | DMSO | 18 | 27 |
5 | ZnBr2 | 2 | DMSO | 18 | 63 |
6 | ZnBr2 | 4 | DMSO | 18 | 64 |
7 | ZnBr2 (3 equiv) | 2 | DMSO | 18 | 49 |
8 | MgCl2 | 2 | DMSO | 18 | 59 |
9 | MgBr2 | 2 | DMSO | 18 | 54 |
10 | Mg(OTf)2 | 2 | DMSO | 18 | 31 |
11 | ZnBr2 | 2 | DMF | 16 | 28 |
12 | MgCl2 | 2 | DMF | 16 | 44 |
13 | MgCl2 | 1.2 | EtOH | 23 | 10 |
14 | MgCl2 | 2.6 | DMSO | 48 | 86 |
15 | MgCl2 | 3 | DMSO | 48 | 22b |
16 | MgCl2 | 3 | DMSO | 48 | 68c |
17d | MgCl2 | 3 | DMSO | 47 | 88 (60e) |
18 | MgCl2 | 2 | DMSO | 24 | 73 |
Determined by 1H NMR integration.
1 mol % of catalyst loading.
5 mol % of catalyst loading.
Conversions in control experiments using conditions of entry 17: Absence of blue LED (0%), absence of 4CzIPN (0%), open to air (67%), replacing silicate with CyBF3K (59%).
Isolated yield.