Table 1.
Optimization of reaction conditionsa
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entry | deviation from standard | GC yield (%)a,b |
1 | none | 63 |
2 | PC-2 instead of PC-1 | 11 |
3 | PC-3 instead of PC-1 | 0 |
4 | Az-2 instead of Az-1 | 14 |
5 | Az-3 instead of Az-1 | 0 |
6 | Az-4 instead of Az-1 | 0 |
7 | Az-5 instead of Az-1 | 11 |
8 | CsOAc instead of Cs2CO3 | 38 |
9 | K2CO3 instead of Cs2CO3 | 8 |
10 | Li2CO3 instead of Cs2CO3 | 0 |
11 | CH3CN instead of THF | 72 |
12 | CH2CI2 instead of THF | 41 |
13 | DMF instead of THF | 65 |
14 | no light | 0 |
15 | no photocatalyst | 0 |
16 | no Az | 0 |
17 | no base | 0 |
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Gas chromatography (GC) yield is based on a calibration curve using 1,3,5-trimethoxybenzene as the internal standard.
Reaction conditions: 1a (0.10 mmol), Bn–HE 2a (0.15 mmol), Az (0.015 mmol), base (0.015 mmol), PC (1 μmol), solvent (0.1 M; THF, tetrahydrofuran; DMF, dimethyformamide) for 16 h.