Table 2. Effect of Temperature on the Reaction [Yields and Isomeric Content (α/β Ratio)]a,b.
| entry | time, h | temperature, °C | yield and isomeric content |
|---|---|---|---|
| 1 | 2 | 60 | 29 (30/70) |
| 2 | 80 | 56 (21/79) | |
| 3 | 100 | 78 (52/48) | |
| 4 | 4 | 60 | 37 (29/71) |
| 5 | 80 | 82 (20/80) | |
| 6 | 100 | 85 (47/53) | |
| 7 | 6 | 60 | 35 (23/77) |
| 8 | 80 | 90 (19/81) | |
| 9 | 100 | 77 (25/75) | |
| 10 | 12 | 60 | 25 (41/59) |
| 11 | 80 | 80 (51/49) | |
| 12 | 100 | 58 (39/61) |
PhC≡CH (5.0 × 10–4 mol, 1 equiv), Et3SiH (5.0 × 10–4 mol, 1 equiv), catalyst 18 (5.0 × 10–7 mol); toluene (0.5 mL).
Yields of products were determined by 1H NMR spectroscopy using 1,2-dimethoxyethane as the standard, whereas the isomeric content was determined on the basis of the alkene coupling constants.