Synthesis and catalytic activity of N-heterocyclic silylene (NHSi) iron (II) hydride for hydrosilylation of aldehydes and ketones

A novel silylene supported iron hydride [Si, C]FeH (PMe3)(3) (1) was synthesized by C (sp(3))-H bond activation with zero-valent iron complex Fe (PMe3)(4). Complex 1 was fully characterized by spectroscopic methods and single crystal X-ray diffraction analysis. To the best of our knowledge, 1 is the first example of silylene-based hydrido chelate iron complex produced through activation of the C (sp(3))-H bond. It was found that complex 1 exhibited excellent catalytic activity for hydrosilylation of aldehydes and ketones. The catalytic system showed good tolerance and catalytic activity for the substrates with different functional groups on the benzene ring. It is worth mentioning that, the experimental results showed that both ketones and aldehydes could be reduced in good to excellent yields under the same catalytic conditions. Based on the experiments and literature reports, a possible catalytic mechanism was proposed.

Automated summary

The novel silylene-supported iron hydride 1 was synthesized via C(sp(3))-H bond activation and exhibited excellent catalytic activity for hydrosilylation of aldehydes and ketones. It showed good tolerance and catalytic activity for substrates with different functional groups on the benzene ring, with both ketones and aldehydes being reduced in good to excellent yields under the same catalytic conditions. A possible catalytic mechanism was proposed based on experiments and literature reports.