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. 2023 Jun 26;13(28):19312–19316. doi: 10.1039/d3ra03510g

Optimization of conditionsa.

graphic file with name d3ra03510g-u1.jpg
Entry Ligand Base Solvent Atmosphere Yield (%)
1 L1 KOH Dioxane Ar 47
2 L1 KOAc Dioxane Ar 23
3 L1 K2CO3 Dioxane Ar 37
4 L1 NaHCO3 Dioxane Ar 43
5 L1 TEA Dioxane Ar 14
6 L1 KOH DMF Ar 27
7 L1 KOH DMSO Ar 14
8 L1 KOH CH3CN Ar n.r.
9 L1 KOH Dioxane/H2O = 4 : 1 Ar 74
10 L1 KOH Dioxane/H2O = 2 : 1 Ar 77
11 L1 KOH H2O Ar 87
12 L2 KOH H2O Ar 75
13 L3 KOH H2O Ar 99
14 L4 KOH H2O Ar 73
15 L5 KOH H2O Ar 83
16 L6 KOH H2O Ar 59
17 L7 KOH H2O Ar 88
18 — KOH H2O Ar n.r.
19 L3 KOH H2O Air 99
20 L3 KOH H2O O2 65
21b L3 KOH H2O Air 41
22c L3 KOH H2O Air 54
23d — KOH H2O Air 67
a

Reaction conditions: 1a (0.20 mmol, 1.0 equiv.), 2a (1.2 equiv.), Pd(OAc)2 (0.05 equiv.), L1–L4 (0.1 equiv.), L5–L7 (0.2 equiv.), base (0.40 mmol, 2.0 equiv.), solvent (1 mL). Yields determined by NMR analysis using CH2Br2 as an internal standard.

b

90 °C.

c

Pd(OAc)2 (0.025 equiv.), L3 (0.05 equiv.).

d

PdCl2(dppf) (0.05 equiv.).