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. 2021 Jan 5;86(2):1901–1910. doi: 10.1021/acs.joc.0c02819

Table 1. Screening of Reaction Conditionsa.

graphic file with name jo0c02819_0008.jpg

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
a

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.

b

Determined by NMR with 1,2,4,5-tetramethylbenzene as internal standard.

c

4 equiv of amine.

d

Under Ar.

e

Under O2.

f

K2S2O8 (2 equiv) used as an additive.

g

Acetic acid (30 equiv) used as additive.

h

Acetic acid (80 equiv) used as additive.

i

Reaction performed in absence of light.

j

Reaction time of 12 h.