Comparison of the results of the photocatalytic direct DCC between various arenes and THF with the photocatalysts and the blended catalystsa.
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Entry | Arene | DCC products | Yield of DCC products, Y (%)b | |||
Pd(3.0)/TiO2 | Pd(2.0)Au(1.0)/TiO2 | TiO2 + Pd(3.0)/Al2O3 | TiO2 + Pd(2.0)Au(1.0)/Al2O3 | |||
1c | 1 | 1a | 0.04(>99) | 0.006(>99) | 0.05(>99) | 0.06(>99) |
2d | 2 | 2a | 1.24(36) | 0.42(32) | 1.06(43) | 1.73(46) |
3e | 3 | 3a | 0.10(80) | 0.08(82) | 0.06(68) | 0.27(57) |
4f | 4 | 4a | 0.05(64) | 0.02(74) | 0.01(50) | 0.03(90) |
5g | 5 | 5a | 0.02(19) | 0.003(6) | 0.02(14) | 0.02(23) |
2 mL (19–24 mmol) of arene, 2 mL (24 mmol) of THF, and 50 mg of the photocatalyst or 100 mg of the blended catalyst were used, other conditions were the same as those described in Table 1.
The total yield, Y (%), of DCC products. The value in parenthesis shows % S. The definition of % Y and % S is mentioned in the Experimental section.
2 mL (22.4 mmol) of benzene (1).
2 mL (19.9 mmol) of benzaldehyde (2).
2 mL (19.4 mmol) of benzonitrile (3).
2 mL (19.01 mmol) of toluene (4).
2 mL (21.9 mmol) of aniline (5).