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. 2023 Feb 10;88(10):6454–6464. doi: 10.1021/acs.joc.2c02952

Table 1. Reaction Scheme and Photocatalysts Employeda.

graphic file with name jo2c02952_0006.jpg

entry base solvent concentration (M) PC yieldb (%)
1 DMF 0.1 11 trace
2 NEt3 DMF 0.1 11 49
3 TMG DMF 0.1 11 51
4 Me-TBD DMF 0.1 11 58
5 TBD DMF 0.1 11 71
6 TBD MeCN 0.1 11 68
7 TBD MeCN 0.05 11 73
8c TBD MeCN 0.05 11 76
9 TBD MeCN 0.05 trace
10c,d TBD MeCN 0.05 11
11c TBD MeCN 0.05 12 73
12c TBD MeCN 0.05 13 71
a

E*ox and E*red refer to the potentials of the PC•+/PC* and PC*/PC•– couples, respectively;24 potentials are reported vs Fc+/Fc (for comparison with literature data: E vs Fc+/Fc = E vs SCE – 0.37 V). The BDFE values are calculated according to eq 1 (vide infra). Optimization of reaction parameters: General conditions are 0.1 mmol of 4a, 1 atm. of CO2, 1 mL of solvent.

b

Yields are given by 1H NMR analysis with dibromomethane as internal standard.

c

2 mol % of 11 was used.

d

No light irradiation.