Table 1.
Photocatalytic nucleophilic addition of alcohols to 1 and 6a.
nucleophile | substrate 1 | substrate 6 | |
yields (%)b of 5 after 12 h irradiation | yields (%)b of 5 after 24 h irradiation | yields (%)b of 7 after 42 h irradiation | |
methanol | 69 | 100 | 32 |
ethanol | 75 | 100 | 21 |
propanol | 64 | 100 | 24 |
butanol | 66 | 100 | 21 |
isopropanol | 63 | 100 | 19 |
tert-butanol | 78 | 98 | 19 |
benzyl alcohol | 52 | 84 | 8c |
phenol | n.d. | 0 | 0 |
aReaction conditions: 1 or 6 (25 mM), Ph–SH (12.5 mM), PDI (0.5 mM), in CH2Cl2/alcohol 3:1 (4 mL), argon atmosphere, 30 °C, 250 mW LED, λ = 530 nm, 1, 6 and products identified and quantified by GC–MS. bAveraged yield from at least two independent reactions. As no byproducts have been detected conversion matches yield. cConversion = 24%.