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. 2014 May 22;16(11):3016–3019. doi: 10.1021/ol501136e

Table 1. Optimization of Reaction Conditionsa.

entry Pd(OAc)2 (mol %) base solvent temp (°C), time yieldb (%)
1 10 KOAc DMF 100, 30 min 19
2 10 KOAc DMF 120, 30 min 36
3 10 KOAc DMF 140, 30 min 42
4 10 KOAc DMF 160, 30 min 66
5 10 KOAc DMF 170, 30 min 51
6 10 KOAc DMF 180, 30 min 49
7 10 KOAc DMF 160, 1 h 84
8 2 KOAc DMF 160, 1 h 45
9 4 KOAc DMF 160, 1 h 56
10 6 KOAc DMF 160, 1 h 68
11 8 KOAc DMF 160, 1 h 78
12 10 CsOAc DMF 160, 1 h 67
13 10 NaOAc DMF 160, 1 h 54
14 10 K2CO3 DMF 160, 1 h 35
15 10 Cs2CO3 DMF 160, 1 h 23
16 10 KOAc DMAc 160, 1 h 77
17 10 KOAc NMP 160, 1 h 62
18 10 KOAc xylene 160, 1 h 35
19 10 KOAc dioxane 160, 1 h 24
20 10 KOAc butan-1-ol 160, 1 h 11
a

Reaction conditions: 1a (1 mmol), 2a (1 mmol), 3a (2 mmol), base (2 mmol), solvent (6 mL).

b

Isolated yield.