Table 1 Optimization of the photo-induced N-N coupling reaction
From: Photo-induced selective N-N bond construction via harnessing nitrene release and transfer
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Entry[a] | S Substitution | Solvent | Light | Yield of 3 (%) | Selectivity of 3: 3’[c] |
1 | 3”-1 | CHCl3 | 365 nm, 50 W | 72 | 6.5: 1 |
2 | 3”-2 | CHCl3 | 365 nm, 50 W | 21 | > 20: 1 |
3 | 3”-3 | CHCl3 | 365 nm, 50 W | Trace | - |
4 | 3”-4 | CHCl3 | 365 nm, 50 W | 23 | > 20: 1 |
5[d] | 3”-1 | DCE | 365 nm, 50 W | 61 | 2.9: 1 |
6[d] | 3”-1 | DCM | 365 nm, 50 W | 25 | 1.9: 1 |
7[d] | 3”-1 | EA | 365 nm, 50 W | 21 | 5.3: 1 |
8[d] | 3”-1 | THF | 365 nm, 50 W | 22 | > 20: 1 |
9[d] | 3”-1 | 1,4-Dioxane | 365 nm, 50 W | 15 | 1.9: 1 |
10[d] | 3”-1 | CH3CN | 365 nm, 50 W | Trace | - |
11[d] | 3”-1 | DMSO | 365 nm, 50 W | Trace | - |
12[d] | 3”-1 | DMF | 365 nm, 50 W | Trace | - |
13 | 3”-1 | CHCl3 | 390 nm, 50 W | 40 | 20: 1 |
14 | 3”-1 | CHCl3 | 450 nm, 50 W | 32 | 6.4: 1 |
15 | 3”-1 | CHCl3 | 365 nm, 30 W | 30 | 1.1: 1 |
16 | 3”-1 | CHCl3 | 365 nm, 100 W | 53 | 3.5: 1 |
17 | 3”-1 | CHCl3 | Under air atmosphere | 31 | 1.6: 1 |
18 | 3”-1 | CHCl3 | No light irradiation | - | - |
