Table 1 Effect of reaction parameters on the copper-catalyzed diazene synthesis using α-tertiary amine
From: Catalytic diazene synthesis from sterically hindered amines for deaminative functionalization
| ||
|---|---|---|
Entry | Variation from the standard conditions | Yield (%) |
1 | None | >99 |
2 | No CuOAc | 7 |
3 | Cu(OAc)2 instead of CuOAc | 22 |
4 | Fe(OAc)2 instead of CuOAc | 21 |
5 | AgOAc instead of CuOAc | 35 |
6 | O2 (1 atm) instead of DBDMH | 0 |
7 | Oxone (3.0 equiv) instead of DBDMH | 0 |
8 | K2S2O8 (3.0 equiv) instead of DBDMH | 0 |
9 | TBHP (3.0 equiv) instead of DBDMH | 0 |
10 | DCDMH instead of DBDMH | 33 |
11 | DIDMH instead of DBDMH | 4 |
12 | NBS (3.0 equiv) instead of DBDMH | >99 |
13 | K2CO3 instead of DBU | 30 |
14 | KOtBu instead of DBU | 25 |
15 | NEt3 instead of DBU | 5 |
16 | DABCO instead of DBU | 60 |
- Reactions were performed on a 0.20 mmol scale.
- Yields were determined by 1H NMR spectroscopic analysis.
