Table 1 Sequential condensation and cyclization of anthranilamide with aldehydes catalyzed by the cages (for reaction details, see Experimental section)
From: Design and self-assembly of hexahedral coordination cages for cascade reactions
| |||||
|---|---|---|---|---|---|
Entry | Catalyst | Catalyst loadinga (mol%) | R 1 | R 2 | Yield (%)b |
1 | TPE-1 | 0.1 | H | Ph | 6a/81 |
2 | TPE-2 | 0.1 | H | Ph | 6a/90 |
3 | TPE-1 | 0.1 | H | 4-FPh | 6b/95 |
4 | TPE-2 | 0.1 | H | 4-FPh | 6b/99 |
5 | TPE-1 | 0 | H | 4-FPh | 6b/0 |
6 | TPE-2 | 0 | H | 4-FPh | 6b/0 |
7 | L1 or L2 | 0.6 | H | 4-FPh | 6b/0 |
8 | 2-PyCHOc | 2.4 | H | 4-FPh | 6b/0 |
9 | Zn(PI)3d | 0.8 | H | 4-FPh | 6b/0 |
10 | Bu4NOTf | 1.6 | H | 4-FPh | 6b/0 |
11 | TPE-1 | 0.1 | H | 4-MeOPh | 6c/78 |
12 | TPE-2 | 0.1 | H | 4-MeOPh | 6c/87 |
13 | TPE-1 | 0.1 | H | 4-MePh | 6d/76 |
14 | TPE-2 | 0.1 | H | 4-MePh | 6d/92 |
15 | TPE-1 | 0.1 | H | 1-naphthyl | 6e/0 |
16 | TPE-2 | 0.1 | H | 1-naphthyl | 6e/99 |
17 | TPE-1 | 0.1 | H | 9-anthral | 6f/0 |
18 | TPE-2 | 0.1 | H | 9-anthral | 6f/0 |
19 | TPE-1 | 0.1 | Me | 4-FPh | 6g/99 |
20 | TPE-2 | 0.1 | Me | 4-FPh | 6g/99 |
21 | TPE-1 | 0.1 | Cl | 4-FPh | 6h/94 |
22 | TPE-2 | 0.1 | Cl | 4-FPh | 6h/96 |
