Table 1.
Entry | Reaction conditions | Yield (%)a | ||||
Starting material |
Reagent / condition type |
Solvent | T (°C) | Time (h) | ||
1 | (R)-isomer | - | - | 110 | 3 | 27 |
2 | (R)-isomer | - | toluene | 110 | 48 | 70 |
3 | (R)-isomer | - | o-xylene | 140 | 48 | 64 |
4 | (R)-isomer | - | ethylene dichloride | 80 | 72 | 40 + 20c |
5 | (R)-isomer | - | CHCl3 | 65 | 72 | 25 |
6 | (R)-isomer | - | toluene | 110 | 48 | 70 |
7 | (R)-isomer | boric acid (1.0 equiv) | toluene (u/N2) | 110 | 24 | 65 |
8 | (R)-isomer | boric acid (1.0 equiv) | toluene | 110 | 24 | 65 |
9 | (R)-isomer | boric acid (0.5 equiv) | toluene | 110 | 48 | 60 |
10 | (R)-isomer | MeSO3H | toluene | 110 | 1 | 27 |
11 | (R)-isomer | tartaric acid | toluene | 110 | 24 | 38 |
12 | (R)-isomer | citric acid | toluene | 110 | 24 | 16 |
13 | (R)-isomer | p-TSA | toluene | 110 | 24 | 38 |
14 | (R)-isomer | sonication | CHCl3 | RT | 2 | 34b |
15 | (R)-isomer | sonication | DMF | RT | 1 | 2b |
16 | (R)-isomer | sonication | ethyl acetate | RT | 1 | 5b |
17 | (R)-isomer | sonication + boric acid | CHCl3 | RT | 1 | 16b |
18 | (R)-isomer | sonication + p-TSA | CHCl3 | RT | 0.5 | 23b |
19 | (R)-isomer | - | toluene | RT | 144 | 3 |
20 | (R)-isomer | - | CHCl3 | RT | 144 | 21b |
21 | (R)-isomer | - | MeOH | RT | 144 | 3b |
22 | (R)-isomer | benzoyl peroxide | toluene | 110 | 48 | 60 |
23 | (R)-isomer | TEMPO | toluene | RT - 110 | 40 | 9b |
24 | (R)-isomer | 2,6-di-tert-butylphenol | toluene | 110 | 24 | 75 |
25 | (S)-isomer | - | toluene | 110 | 48 | 70 |
26 | (R)-isomer | MW 150 Watt | DMF | 150 | 0.5 | 70 |
aIsolated yield, b% conversion in HPLC, crecovered starting material with SOR +5°