Pd(acac)₂/Xantphos: A highly efficient and readily available catalyst for regioselective hydrosilylation of allenes

Abstract

A convenient and efficient Pd(acac)₂/Xantphos-catalyzed regioselective hydrosilylation of allenes has been developed. This convenient catalyst proved to be suitable for a broad range of allenes, offering a general and efficient route to branched allylsilanes in high yields with exceptional regioselectivity. A Pd(0) species involved mechanism is proposed.

Graphical Abstract

Keywords:

• Hydrosilylation
• branched allylsilanes

Notes

1 General procedure for hydrosilylation of allenes: In a nitrogen-filled Schlenk tube, Pd(acac)₂ (6 mg, 2 mmol%), Xantphos (12 mg, 2 mol%) were added to THF (1 mL), followed by the addition of allene (1 mmol) and PhSiH₃ (130 mg, 1.2 mmol) in THF (1 mL) under nitrogen. The reaction mixture was stirred at 30 °C. When the reaction was completed (0.5–3 h, monitored by TLC), the solvent was removed in vacuum. The crude product was purified directly by silica gel column chromatography eluting with petroleum ether and ethyl acetate to afford the corresponding product. The Supplemental Materials contains sample ¹H and ¹³C NMR spectra of the products 2 (Figures S1 – S13).

Additional information

Funding

We are grateful to the National Natural Science Foundation of China [Nos. 21772166 and 91845101].