Table 2. Dehydrogenative penta-alkenylation of 1 a , b .
| ||||
| Carborane |
Alkene |
Product | ||
| 1a | X = H | R = aryl | R = C6H4-4-F | 3a 86% |
| X = H | R = C6H5 | 3b 75% | ||
| X = H | R = C6H4-4-CF3 | 3c 70% | ||
| X = H | R = C6H4-4-CN | 3d 63% | ||
| X = H | R = C6F5 | 3e 53% | ||
| X = H | R = benzyl | R = CH2-C6H5 | 3f 72% | |
| X = H | R = CH2-C6F5 | 3g 59% | ||
| X = H | R = alkyl |
|
3h 81% | |
| X = H |
|
3i 84% | ||
| X = H |
|
3j 82% | ||
| X = H |
|
3k 79% | ||
| X = H |
|
3l 76% | ||
| X = H |
|
3m 66% | ||
| X = H |
|
3n 74% | ||
| 1b | X = Cl | R = aryl | R = C6H5 | 3o 71% |
| 1c | X = Br | R = C6H4-4-F | 3p 78% | |
| 1d | X = Me | R = C6H4-4-F | 3q 82% | |
| 1e | X = Ph | R = C6H5 | 3r 62% | |
| 1e | X = Ph | R = C6H4-4-F | 3s 69% | |
| 1f | X = CN | R = C6H4-4-F | 3t 72% | |
a 1 (0.15 mmol), 2 (0.81 mmol), Pd(OAc)2 (0.015 mmol), AgOAc (1.5 mmol), in acetonitrile (4 mL); for further details, see the ESI.
bYields = isolated yields after purification by silica gel chromatography.