Optimization of reaction conditionsa.
Entry | Deviation from std. conditions | % Yieldb | Entry | Deviation from std. conditions | % Yieldb |
---|---|---|---|---|---|
1 | None | 89 | 10 | PC10 instead PC1 | nr |
2 | PC2 instead PC1 | 81 | 11 | PC11 instead PC1 | Trace |
3 | PC3 instead PC1 | 67 | 12 | PC12 instead PC1 | nr |
4 | PC4 instead PC1 | 91 | 13 | PC13 instead PC1 | nr |
5 | PC5 instead PC1 | 89 | 14 | 20 mol% Cu(OTf)2 | 32 |
6 | PC6 instead PC1 | 52 | 15 | 20 mol% Yb(OTf)3 | 36 |
7 | PC7 instead PC1 | 58 | 16 | No PC | nr |
8 | PC8 instead PC1 | 68 | 17 | No light | nr |
9 | PC9 instead PC1 | 81 |
Reaction conditions: styrene 1a (0.1 or 0.2 mmol), RAE 2a (1.5 equiv.), potassium organotrifluoroborate salt 3a (2 equiv.), Ir(ppy)3 (3 mol%) in MeCN (0.1 M), 24 h irradiation with blue LEDs (λmax = 456 nm).
Yields were determined by 1H NMR analysis using trimethoxybenzene as internal standard. Abbreviations: std, standard; nr, no reaction.