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. 2022 Nov 7;12(49):31680–31687. doi: 10.1039/d2ra03725d

The study results on the effect of various solvents on the A3-coupling preparation of propargylaminea.

graphic file with name d2ra03725d-u1.jpg
Entry Solvent Base Temp. (°C) Cat. (mol%) Time (h) Yieldb (%)
1 CH3CN KOH 60 0.05 10 75
2 CH3CN KOH 60 0.1 10 75
3 EtOH KOH 80 0.05 10 45
4 EG KOH 100 0.05 10 61
5 CHCl3 K2CO3 60 0.1 10 92
6 CHCl3 Cs2CO3 60 0.1 10 96
7 CHCl3 KOH 60 0.1 10 87
9 CHCl3 NaOH 60 0.1 10 84
10 CHCl3 Et3N 60 0.1 10 76
a

Reaction conditions: 1.2 mmol of morpholine, 1 mmol of benzaldehyde, and 1.3 mmol of phenylacetylene.

b

Isolated yields.