Optimization of reaction conditionsab.
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Entrya | PC | PC (mol%) | Additive | Solvent | LED | Yieldb (%) |
1 | Xanthone | 5.0 | — | MeCN | 365 nm | 15 |
2 | Thioxanthone | 5.0 | — | MeCN | 365 nm | — |
3 | fac-Ir(ppy)3 | 5.0 | — | MeCN | 365 nm | — |
4 | PC 1 | 5.0 | — | MeCN | 365 nm | 79 |
5 | PC 2 | 5.0 | — | MeCN | 365 nm | 88 |
6 | PC 3 | 5.0 | — | MeCN | 365 nm | — |
7 | PC 4 | 5.0 | — | MeCN | 365 nm | — |
8 | PC 2 | 5.0 | — | MeCN | 385 nm | 90 |
9 | PC 2 | 5.0 | — | MeCN | Blue LED (100 W) | 88 |
10 | PC 2 | 1.0 | — | MeCN | 385 nm | 83 |
11 | PC 2 | 2.0 | — | MeCN | 385 nm | 91 (90) c |
12 | PC 2 | 3.0 | — | MeCN | 385 nm | 81 |
13 | PC 2 | 4.0 | — | MeCN | 385 nm | 83 |
14 | PC 2 | 2.0 | — | THF | 385 nm | <5 |
15 | PC 2 | 2.0 | — | DMF | 385 nm | — |
16 | PC 2 | 2.0 | — | DCM | 385 nm | 51 |
17d | PC 2 | 5.0 | DIPEA | MeCN | 385 nm | 29 |
18d | PC 2 | 5.0 | Hantzsch ester | MeCN | 385 nm | — |
19 | — | — | — | MeCN | 385 nm | — |
20e | PC 2 | 2.0 | — | MeCN | 385 nm | — |
21f | PC 2 | 2.0 | — | MeCN | 385 nm | 82c |
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Reaction conditions: 1a (0.1 mmol) and PC (x mol%) were added to degassed MeCN (2.0 mL) under an Ar atmosphere for 12.0 h, in a sealed tube using LED light irradiation.
NMR yield using 1,3,5-trimethoxybenzene as an internal standard.
Yield of the isolated products.
Additive (0.2 mmol) was used.
Under dark conditions.
A scale-up reaction with 1.0 mmol of 1a.