Catalytic hydrosilylation reaction of aldehydes using high oxidation state oxo rhenium(V) pincer complex [Re(O)2(PNN)][OTf] (2) with organosilanes is descried. Catalyst loading of 0.1 mol % [Re] was sufficient for complete hydrosilylation of aldehydes within 5 minutes at room temperature. Good to excellent yields of silyl ether products are obtained in one step, and a variety of functional groups are compatible. A screening of silanes revealed primary and secondary aromatic silanes to be most effective in catalytic hydrosilylation with 2. A maximum turnover frequency (TOF) of 5.6 x 105 h-1 at was obtained at room temperature for hydrosilylation of benzaldehyde. A Hammett study for various para substituted benzaldehydes showed linear correlation with positive r values of 0.84 at room temperature. The system 2/PhSiH3 is also highly efficient for deoxygenation of silyl ether product under high temperature, producing selectively the corresponding alkanes.

High efficient pincer oxo-rhenium catalyst for hydrosilylation

2019 Fall National Meeting

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