Table 1. Screening of Reaction Conditionsa.
entry | solvent | light source | yield of 3a (%)b | d.r.b |
---|---|---|---|---|
1 | acetonitrile | CFL | 25 | >25:1 |
2 | methanol | CFL | 14 | >25:1 |
3 | tetrahydrofuran | CFL | 29 | >25:1 |
4 | ethyl acetate | CFL | 17 | >25:1 |
5 | dichloromethane | CFL | 40 | >25:1 |
6 | 1,2-dichloroethane | CFL | 41 | >25:1 |
7 | 1,2-dimethoxyethane | CFL | 32 | >25:1 |
8 | 1,4-dioxane | CFL | 65 | >25:1 |
9 | 1,4-dioxane | CFL | 30c | >25:1 |
10 | 1,4-dioxane | CFL | 0d | – |
11 | 1,4-dioxane | CFL | 12e | >25:1 |
12 | 1,4-dioxane | CFL | 37f | >25:1 |
13 | 1,4-dioxane/water (2:1) | CFL | 47f | >25:1 |
14 | 1,4-dioxane | blue LED | 23 | >25:1 |
15 | 1,4-dioxane | CFL | 68g | >25:1 |
16 | 1,4-dioxane | CFL | 73h | >25:1 |
17 | 1,4-dioxane | UV-CFL | 30 | >25:1 |
18 | 1,4-dioxane | – | 0i | – |
19 | 1,4-dioxane | blue LED | 60h,j | >25:1 |
Reaction conditions: 1a (0.7 mmol) and 2a (0.1 mmol) in 3 mL of solvent irradiated with two 15 W compact fluorescent lamps in room temperature for 4 h.
Determined by NMR with 1,2,4,5-tetramethylbenzene as internal standard.
4 equiv of amine.
Under Ar.
Under O2.
K2S2O8 (2 equiv) used as an additive.
Acetic acid (30 equiv) used as additive.
Acetic acid (80 equiv) used as additive.
Reaction performed in absence of light.
Reaction time of 12 h.