Table 1. Screening Reaction Conditions.
entry | catalyst | mol % | solvent | yield (%) |
---|---|---|---|---|
1 | PdCl2 | 10 | (CH2Cl)2 | 57a |
2 | PdCl2 | 10 | CH2Cl2 | 92 |
3 | PdCl2b | 10 | CH2Cl2 | 93 |
4 | PdCl2 | 5 | CH2Cl2 | 92 |
5 | PdCl2 | 5 | CH2Cl2 | 91c |
6 | PdCl2 | 2 | CH2Cl2 | 45 |
7 | PdCl2(CH3CN)2 | 5 | CH2Cl2 | 82 |
8 | Pd(OAc)2 | 10 | CH2Cl2 | 0d |
9 | Pd/Ce | CH2Cl2 | 0d | |
10 | Pd/Cf | 5 | CH2Cl2 | 0d |
11 | PdCl2(PPh3)2 | 10 | CH2Cl2 | 0d |
12 | Pd2(dba)3 | 5 | CH2Cl2 | 0d |
Reaction conducted at 50 °C; 3-ethyl-1H-isochromen-1-one (1c) was isolated.
PdCl2 (99.999%).
1.0 mmol of 1a was used.
Starting material recovered.
Palladium (5%) on activated charcoal, 1 equiv.
Palladium (5%; 5 mol %) on activated charcoal and 5 mol % of LiCl.