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. 2022 Jan 19;27(3):630. doi: 10.3390/molecules27030630

Table 1.

Evaluation of the reaction conditions 1.

graphic file with name molecules-27-00630-i001.jpg

Entry Catalyst Solvent, Base Temp Yield 2
1 XPhos Pd G3 DMF, K3PO4 60 °C 31%
2 XPhos Pd G3 DMF, K3PO4 80 °C 41%
3 RuPhos Pd G3 DMF, K3PO4 60 °C 0 %
4 BINAP Pd G3 DMF, K3PO4 60 °C 38%
5 DPPE Pd G3 DMF, K3PO4 60 °C 16%
6 DPPPY Pd G3 DMF, K3PO4 60 °C 77%
7 DPPPY Pd G3 DMF, K3PO4 80 °C 89%
8 DPPPY Pd G3 DMF, MeOK 80 °C 0%
9 DPPPY Pd G3 DMF, KHMDS 80 °C 28%
10 DPPPY Pd G3 DMF, NaOH 80 °C 40%
11 DPPPY Pd G3 THF, K3PO4 80 °C 20%
11 DPPPY Pd G3 Toluene, K3PO4 80 °C 0%

1 Conditions: L Pd G3 (2 mol%), dimethyl 2-(hex-4-yn-1-yl)malonate (0.100 mmol, 1 equiv.), PhBr (0.150 mmol, 1.5 equiv.), K3PO4 (0.150 mmol, 1.5 equiv.), DMF (0.5 mL), 60–80 °C, 6 h. 2 Determined by GC with mesitylene as an internal standard. Optimal conditions in bold.