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. 2020 Jan 10;11(8):2130–2135. doi: 10.1039/c9sc06184c

The model reaction and the reaction parameters evaluated.

graphic file with name c9sc06184c-u1.jpg
Entrya Change from standard conditions Yieldb (%)
1 None 87
2 No light 0
3 No light and heated to 80 °C 0
4 A 23 W CFL, instead of a blue LED 56
5 A 30 W white LED, instead of a blue LED 50
6 No base 0
7 KHCO3, instead of Cs2CO3 53
8 Na2CO3, instead of Cs2CO3 40
9 K2CO3, instead of Cs2CO3 73
10 K3PO4, instead of Cs2CO3 43
11 DBU, instead of Cs2CO3 51
12 TMG, instead of Cs2CO3 54
13 Et3N, instead of Cs2CO3 15
14 DMF, instead of DMSO 72
15 CH3CN, instead of DMSO 50
16 Acetone, instead of DMSO 66
17 DCM, instead of DMSO 18
a

Conditions: 1.0 equiv. of 4′-bromoacetophenone 1, 2.0 equiv. of methyl 4-hydroxycinnamate 2, 3.0 equiv. of base [0.10 M]; all solvents were rigorously degassed by freeze/pump/thaw cycles.

b

Isolated yields by chromatography.