Table 1. Optimization of the One-Pot RCM/Oxidation/1,3-Dipolar Cycloaddition Protocol.
| RCM |
1,3-dipolar cycloaddition |
isolated yield | |||||||
|---|---|---|---|---|---|---|---|---|---|
| entry | Grubbs II (mol %) | solvent | temp. (°C) | conc. (M) | time (min) | temp. (°C) | conc. (M) | time (min) | (%, two steps) |
| 1 | 10 | benzene | reflux | 0.01 | 30 | reflux | 0.01 | 60 | 15 |
| 2 | 20 | benzene | reflux | 0.01 | 30 | reflux | 0.01 | 60 | 11 |
| 3 | 5 | benzene | reflux | 0.01 | 30 | reflux | 0.01 | 60 | 16 |
| 4 | 1 | benzene | reflux | 0.01 | 30 | reflux | 0.01 | 60 | 18 |
| 5 | 1 | toluene | 80 | 0.01 | 30 | 80 | 0.01 | 60 | 18 |
| 6 | 1 | toluene | 80 | 0.01 | 10 | 80 | 0.01 | 30 | 18 |
| 7a | 1 | toluene | 80 | 0.1 | 10 | 80 | 0.1 | 30 | 5 |
| 8b | 1 | toluene | 80 | 0.01 | 10 | 80 | 0.01 | 30 | 15 |
Cross metathesis product was also isolated in 28% yield.
Reaction was performed in a glovebox.
