Issue 9, 2024

Iron complexes supported by silyl-NHC chelate ligands: synthesis and use for double hydroboration of nitriles

Abstract

Iron complexes bearing new silyl-NHC bidentate ligands were synthesised by treating Fe3(CO)12 with a mixture of N-(hydrosilyl)methyl imidazolium salts and a base. These complexes showed high performance in the catalytic double hydroboration of nitrile with pinacolborane (HBpin) to produce N,N-bis(boryl)amine by a combination of UV irradiation and mild heating (60 °C). The product yields for the hydroboration of aromatic and aliphatic nitriles reached 85%–95% (NMR) using an iron complex (5 mol%). Reducing the loading amount of the iron complex to 0.5 mol% still afforded the products in high yields. An analogous ruthenium complex, which was similarly synthesised using Ru3(CO)12, showed lower activity. Stoichiometric reactions of the iron complex with nitriles afforded Fe(0)-N-silylimine complexes, which may be dormant states in nitrile hydroboration. A catalytic mechanism including Fe(0) N-silylimine species is proposed.

Graphical abstract: Iron complexes supported by silyl-NHC chelate ligands: synthesis and use for double hydroboration of nitriles

Supplementary files

Article information

Article type
Paper
Submitted
27 Oct 2023
Accepted
24 Jan 2024
First published
26 Jan 2024

Dalton Trans., 2024,53, 4041-4047

Iron complexes supported by silyl-NHC chelate ligands: synthesis and use for double hydroboration of nitriles

T. Komuro, K. Hayasaka, K. Takahashi, N. Ishiwata, K. Yamauchi, H. Tobita and H. Hashimoto, Dalton Trans., 2024, 53, 4041 DOI: 10.1039/D3DT03605G

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