Table 1. Screening of the reaction conditions a .
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Entry | Ligand | Base | Solvent | 3Aa b (%) |
1 | dcype | Cs2CO3 | 1,4-Dioxane | 0 |
2 | dcype | K3PO4 | t-AmylOH | 83 |
3 | dcype | K3PO4 | t-BuOH | 70 |
4 | dcype | K3PO4 | 1,4-Dioxane | 0 |
5 | dcype | K3PO4 | DMF | 0 |
6 | dcype | K3PO4 | i-PrOH | 0 |
7 | dcype | Cs2CO3 | t-AmylOH | 44 |
8 | dcype | LiOt-Bu | t-AmylOH | 59 |
9 | dcype | KOt-Bu | t-AmylOH | 0 |
10 | PCy3 | K3PO4 | t-AmylOH | 0 |
11 | IPr·HCl | K3PO4 | t-AmylOH | 0 |
12 | dcypt | K3PO4 | t-AmylOH | 55 |
13 | L1 | K3PO4 | t-AmylOH | 53 |
14 | L2 | K3PO4 | t-AmylOH | 64 |
15 c | dcype | K3PO4 | t-AmylOH | 82 |
aUnless otherwise noted, the reaction conditions were as follows: 1A (0.40 mmol), 2a (1.5 equiv.), Ni(cod)2 (10 mol%), ligand (bidentate: 12 mol%, monodentate: 24 mol%), base (3.0 equiv.), solvent (1.6 mL), 110 °C, and 12 h.
bGC yield.
cNi(OTf)2 (10 mol%) was used.