Optimization of the reaction conditions for the photocatalytic HAT-reaction of ethylbenzene with acetone as an electrophilea.
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| Entry | Amount of 2a | Photocatalyst (mol%) | Amount of (iPr)3SiSH | Amount of base | Additive | Yieldb [%] |
| 1 | 10 eq. | 4CzIPN (5) | 20 mol% | 20 mol% | — | 3 |
| 2 | 10 eq. | 4CzIPN (5) | 20 mol% | 20 mol% | 4 Å MS (100 mg) | 21 |
| 3 | Co-solvent (1 : 1) | 4CzIPN (5) | 20 mol% | 20 mol% | 4 Å MS (100 mg) | 49 |
| 4 | 10 eq. | 4CzIPN (5) | 10 mol% | 20 mol% | 4 Å MS (50 mg) | 30 |
| 5 | 10 eq. | 3DPA2FBN (5) | 10 mol% | 20 mol% | 4 Å MS (50 mg) | 50 |
| 6 | Co-solvent (1 : 1) | 3DPA2FBN (5) | 10 mol% | 20 mol% | 4 Å MS (50 mg) | 86 |
| 7 | 10 eq. | 3DPA2FBN (3) | 10 mol% | 10 mol% | 4 Å MS (50 mg) | 59 |
| 8 | 10 eq. | 3DPA2FBN (5) | 10 mol% | — | 4 Å MS (50 mg) | 27 |
| 9 | 10 | — | 10 mol% | 20 mol% | 4 Å MS (100 mg) | 0 |
| 10c | 10 | 4CzIPN (5) | 10 mol% | 20 mol% | 4 Å MS (100 mg) | 0 |
| 11 | 10 | 4CzIPN (5) | — | 20 mol% | 4 Å MS (100 mg) | 0 |
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a
The reaction was performed using 1 eq. (0.2 mmol) 1a in 2 mL degassed solvent.
b
Yields were determined with GC-FID analysis using n-decane as an internal standard.
c
Reaction was performed in the dark.