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. 2023 Aug 23;88(17):12738–12743. doi: 10.1021/acs.joc.3c01429

Table 1. Optimization of Reaction Conditionsa.

graphic file with name jo3c01429_0004.jpg

entry [M] ligand base solvent temp (°C) yield (%)b
1 CuI – K2CO3 DMF 100 0
2 AgOTf – K2CO3 DMF 100 0
3 Pd(OAc)2 – K2CO3 DMF 100 54
4 PdCl2 – K2CO3 DMF 100 31
5 Pd(PPh3)2Cl2 – K2CO3 DMF 100 40
6 Pd(PPh3)4 – K2CO3 DMF 100 48
7 Pd(OAc)2 PPh3 K2CO3 DMF 100 70
8 Pd(OAc)2 Xantphos K2CO3 DMF 100 68
9 Pd(OAc)2 P(4-MeOC6H4)3 K2CO3 DMF 100 64
10 Pd(OAc)2 P(4-MeC6H4)3 K2CO3 DMF 100 69
11 Pd(OAc)2 PPh3 Na2CO3 DMF 100 64
12 Pd(OAc)2 PPh3 Cs2CO3 DMF 100 72
13 Pd(OAc)2 PPh3 tBuOK DMF 100 67
14c Pd(OAc)2/CuI PPh3 Cs2CO3 DMF 110 0
15 Pd(OAc)2 PPh3 Cs2CO3 DMF 80 57
16 Pd(OAc)2 PPh3 Cs2CO3 DMF 110 73
17 Pd(OAc)2 PPh3 Cs2CO3 DMF 120 75
18 Pd(OAc)2 PPh3 Cs2CO3 DMF 130 73
19 Pd(OAc)2 PPh3 Cs2CO3 DMSO 120 73
20 Pd(OAc)2 PPh3 Cs2CO3 DMA 120 72
21 Pd(OAc)2 PPh3 Cs2CO3 xylene 120 65
22 Pd(OAc)2 PPh3 Cs2CO3 toluene 120 70
23 – PPh3 Cs2CO3 DMF 120 0
a

Reaction conditions: Reactions were carried out with 1a (107 mg, 0.50 mmol), 2a (121 mg, 0.60 mmol), catalyst (10 mol %), ligand (20 mol %), and base (1.0 mmol) in solvent (5.0 mL) under argon for 10 h.

b

Isolated yields of 3a after purification by column chromatography.

c

Reaction was carried out with 1a (107 mg, 0.50 mmol), 2a (121 mg, 0.60 mmol), Pd(OAc)2 (5 mol %), CuI (10 mol %), PPh3 (20 mol %), and Cs2CO3 (0.5 mmol) in DMF (5.0 mL) under argon for 8 h.