Table 2. Evaluation of Different Catalysts for the One-Pot Hydrosilylation of Styrene with PhSiH3 Coupled with Catalytic Dehydrogenative Coupling of PhSiH3 with Methanola.
entry | catalystb | conv. (%)b | A (%) | B (%) | C (%) | D (%) | E (%) | F (%) |
---|---|---|---|---|---|---|---|---|
1 | [Co(OAc)(H2O)2(tpy)]OAc (cat-1)c | >99 | 5 | 95 | ||||
2 | Co(OAc)2·4H2O | >99 | >99 | |||||
3 | Co(acac)2·H2O | >99 | >99 | |||||
4 | Co(NO3)2·6H2O | 33 | 14.3 | 18.7 | ||||
5 | Fe(OAc)2 + tpy | >99 | >99 | |||||
6 | Fe(OAc)2·9H2O | >99 | >99 | |||||
7 | Ni(OAc)2 + tpy | >99 | 4.4 | 26.3 | 51.8 | 17.5 | ||
8 | Ni(OAc)2·4H2O | >99 | 41.4 | 36 | 22.6 | |||
9 | tpy | 0 | ||||||
10 | Karstedt catalystd | >99 | 34 | 66 |
All reactions were performed with 0.89 mmol of phenylsilane, 0.89 mmol of styrene, and 0.1% of catalyst in 0.2 mL of methanol under aerobic conditions.
Disappearance of phenylsilane determined by 1H-NMR analysis of the crude reaction mixture using 1,4-dinitrobenzene as the standard.
6 h of reaction time.
Pt2[(Me2SiCH=CH2)2O]3.