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. 2019 Mar 4;55(24):3489–3492. doi: 10.1039/c9cc00492k

Table 1. Optimization of the reaction conditions. 1a (0.1 mmol), DBAD (0.15 mmol), CeCl3·7H2O (10 mol%), CH3CN (0.1 M) at 25 °C, 455 nm LED for 24 h.

Inline graphic
Entry Deviation from standard conditions 3a a (%)
1 None 90 (80) b
2 CeCl3 instead of CeCl3·7H2O 80
3 Ce(OTf)3 instead of CeCl3·7H2O 66
4 Ce(OTf)4 instead of CeCl3·7H2O 63
5 K2CO3 instead of Cs2CO3 66
6 Na2CO3 instead of Cs2CO3 55
7 Li2CO3 instead of Cs2CO3 25
8 NaHCO3 instead of Cs2CO3 23
9 Without base 20
10 DCM instead of CH3CN 85
11 DCE instead of CH3CN 86
12 CHCl3 instead of CH3CN 66
13 DMSO instead of CH3CN 61
14 Without light 0
15 Without CeCl3·7H2O 0

aNMR yields using benzoyl benzoate as internal standard.

bIsolated yield.