Table 1. Scoping Conditions Explored for the PR Reactiona.
| solvent | calculated Hammett parameter68 | catalyst dose 1 | catalyst dose 2 | temperature (°C) | reaction resultb |
|---|---|---|---|---|---|
| toluene | –0.170 | 5 mol % | 100 | (−) | |
| 25 | (−) | ||||
| 5 mol % | 100 | (o) | |||
| 25 | (−) | ||||
| 1,2-dichlorobenzene | 0.454 | 5 mol % | 100 | (−) | |
| 25 | (−) | ||||
| 5 mol % | 100 | (o) | |||
| 25 | (−) | ||||
| chlorobenzene | 0.227 | 5 mol % | 100 | (−) | |
| 25 | (−) | ||||
| 5 mol % | 100 | (−) | |||
| 25 | (−) | ||||
| nitrobenzene | 0.778 | 5 mol % | 100 | (−) | |
| 25 | (−) | ||||
| 5 mol % | 100 | (+) | |||
| 25 | (−) | ||||
| dichloromethane | 5 mol % | 100 | (−) | ||
| 5 mol % | 25 | (−) | |||
| xylenes | –0.247 | 5 mol % | 100 | (−) | |
| 25 | (−) | ||||
| 5 mol % | 100 | (−) | |||
| 25 | (−) |
a
(−)—No axial substituted bis(tri-n-hexylsilyl oxide)silicon phthalocyanine, (3HS)2-SiPc, formed; (o)—modest axial substituted (3HS)2-SiPc formed; (+)—full functionalization axial substitute (3HS)2-SiPc achieved.
b
(o) denotes a partially positive result.