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. Author manuscript; available in PMC: 2023 Apr 21.
Published in final edited form as: Chem Catal. 2022 Apr 5;2(4):898–907. doi: 10.1016/j.checat.2022.03.007

Table 1.

Optimization of the reaction conditions

graphic file with name nihms-1795335-t0001.jpg
Entry Additive Equiv of Additive 3a/IS GC yield (%)a
1 none none 23
2 CS2CO3 1 43
3 K2CO3 1 39
4 Na2CO3 1 37
5 K3PO4 1 30
6 NaOAc 1 18
7 NH4OAc 1 19
8b Cs2CO3 1 52
9b Cs2CO3 2 69
10b,c Cs2CO3 2 87 (78d)
11b,c CsF 2 63
12b,c,e Cs2CO3 2 72
13b,c,f Cs2CO3 2 Traces
14b,c, g Cs2CO3 2 no reaction

Reaction conditions: 1a (0.1 mmol), 2a (0.1 mmol), base, dry and degassed DMSO (0.2 M) at room temperature under purple Kessil® (390 nm) irradiation for 16 h.

a

Calculated against 1,3,5-trimethoxybenzene as internal standard (IS).

b

3 equiv of 2a.

c

Solvent 0.13 M for 1a.

d

Isolated yield at 0.5 mmol scale.

e

Blue Kessil® (456 nm).

f

Green Kessil® (525 nm).

g

No light.