Table 1. Evaluation of the conditions for the Co-catalyzed hydrosilylation of 1-phenyl-1,3-butadiene a .
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Entry | Ligand | Temperature | Conversion b (%) | Yield of 1a b (%) | 1a/2a/3a b |
1 | PhPDI | 50 °C | >99 | 27 | 31 : — : 69 |
2 | TFAPDI | 50 °C | >99 | 33 | 35 : — : 65 |
3 | PyBox | 50 °C | >99 | 49 | 56 : 4 : 40 |
4 | dppm | 50 °C | 28 | 23 | >99 : — : — |
5 | dppe | 50 °C | 78 | 77 | >99 : — : — |
6 | dppbz | 50 °C | 9 | 5 | >99 : — : — |
7 | binap | 50 °C | 93 | 76 | >99 : — : — |
8 | xantphos | 50 °C | >99 | 81 | >99 : — : — |
9 c | xantphos | rt | >99 | 87 | >99 : — : — |
10 c , d | xantphos | rt | >99 | 83 | 96 : 4 : — |
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aConditions: (E)-diene (0.400 mmol), PhSiH3 (0.500 mmol), Co(acac)2 (12.0 μmol), ligand (12.0 μmol), and THF (1 mL) for 3 h.
bThe conversion of diene, yield of 1a, and the ratio of products 1a, 2a, and 3a were determined by GC analysis with tridecane as the internal standard.
cCatalyst (1 mol%).
dA mixture of (E/Z)-1-phenyl-1,3-butadiene (E/Z = 45 : 55) was used.