Optimization of the photocatalytic decarboxylative cyanation with isonitrilesa.
| ||||
|---|---|---|---|---|
| Entry | Solvent | 2 (equiv.) | Ir-cat (mol%) | Yield 3 (3′) % |
| 1 | MeCN | 2a (3.0) | 2 | 68 (14) |
| 2 | MeCN | 2b (3.0) | 2 | 55 (35) |
| 3 | MeCN | 2c (3.0) | 2 | 30 (5) |
| 4 | MeCN | 2d (3.0) | 2 | 48 (52) |
| 5 | MeCN | 2e (3.0) | 2 | 24 (0) |
| 6 | MeCN | 2f (3.0) | 2 | 4 (12) |
| 7 | DMSO | 2a (3.0) | 2 | 74 (12) |
| 8 | DMF | 2a (3.0) | 2 | 60 (14) |
| 9 | DCM | 2a (3.0) | 2 | 0 (5) |
| 10 | PhCH3 | 2a (3.0) | 2 | 36 (30) |
| 11b,c | DMSO | 2a (2.5) | 1 | 82 (8) |
| 12d | DMSO | 2a (2.5) | 1 | 0 |
| 13e | DMSO | 2a (2.5) | 1 | 0 |
The reactions were performed on a 0.10 mmol scale and the yields were determined by 1H NMR with CH2Br2 as an internal standard.
The reaction was performed on a 0.20 mmol scale.
Yield determined after isolation by column chromatography purification.
The reaction was performed in the absence of light.
The reaction was performed in the absence of photocatalyst. See ESI for further details.