Table 2.
Optimization of the allylic C-H functionalization Reaction[a]
 | |||||
|---|---|---|---|---|---|
| entry | Catalyst | Temp(°C) | Yield[b] | r.r. [c] (15a:16a) | d.r.[c] (15a) |
| 1 | Rh2(S-NTTL)4 | rt | 98% | 78:22 | 1:1 |
| 2 | Rh2(R-DOSP)4 | rt | 41% | 67:33 | 3:1 |
| 3 | Rh2(S-TCPTAD)4 | rt | 97% | 29:71 | 1:1 |
| 4 | Rh2(R-PTAD)4 | rt | 93% | 64:36 | 1:2 |
| 5 | Rh2(S-TPPTTL)4 | rt | 99% | 92:8 | 7:1 |
| 6 | Rh2(S-TPPTTL)4 | −20 | 99% | 93:7 | 9:1 |
| 7 | Rh2(S-TPPTTL)4 and HFIP additive[d] | −20 | 99% | 92:8 | 7.3:1 |
[a]
Reaction conditions: 9a (0.8 mmol), 14a (0.2 mmol), [Rh] catalyst (1 mol %), 3 h reaction time.
[b]
combined 1H-NMR yield of 15a and 16a.
[c]
determined from crude 1H-NMR
[d]
using 2.0 equiv of additive.