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. 2019 Dec 17;11(5):1418–1424. doi: 10.1039/c9sc04880d

Optimization of reaction conditionsa.

graphic file with name c9sc04880d-u1.jpg
Entry Base Solvent Time Yieldb (%)
1 Cs2CO3 CH3CN 58 h 12
2 K2CO3 CH3CN 18 h 15
3 Na2CO3 CH3CN 18 h 12
4 NaOH CH3CN 18 h 30
5 DABCO·6H2O CH3CN 27 h 16
6 DBU CH3CN 33 h 45
7 NEt3 CH3CN 3 h 32
8 TMG CH3CN 5 min 87c
9 TMG CHCl3 4 h 82
10 TMG Toluene 4 h 74c
11 TMG EtOAc 20 min 58
12d TMG CH3CN 5 min 95c
13e TMG CH3CN 5 min 80c
a

Unless otherwise noted, the reactions were conducted with 0.15 mmol 1a with 2.0 equivalents of 2a in the presence of 2.0 equivalents of base in 0.8 mL of specified solvent at 60 °C.

b

Isolated yields obtained by column chromatography.

c

Isolated yields obtained by filtration of the precipitate.

d

2.2 equivalents of 2a were used.

e

2.4 equivalents of 2a were used. DABCO = 1,4-diazabicyclo[2.2.2]octane; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene; TMG = 1,1,3,3-tetramethylguanidine.