Though surprising – when compared with well-established poly-fluoromethyl silanes (e.g., Ruppert-Prakash reagent, TMSCF3) – α-mono-fluoromethyl silanes are underrepresented motifs in chemical synthesis, having been – so far – reported no more than 2–3 examples. We propose herein the nucleophilic substitution on the silicon atom of chlorosilanes – with fluoromethyllithium (LiCH2F) – as a general strategy for their direct preparation. The procedure - exhibiting remarkable dependance on steric elements across silicon – can be advantageously extended to prepare distinct IV-row heteroatom-centered analogues such as tin and germanium organometallics.

Preparation of α‐ Mono ‐Fluoromethyl Silanes via Nucleophilic Displacement on Chlorosilanes With LiCH 2 F

Nardi, Alberto;Miele, Margherita;Pace, Vittorio
2026-01-01

Abstract

Though surprising – when compared with well-established poly-fluoromethyl silanes (e.g., Ruppert-Prakash reagent, TMSCF3) – α-mono-fluoromethyl silanes are underrepresented motifs in chemical synthesis, having been – so far – reported no more than 2–3 examples. We propose herein the nucleophilic substitution on the silicon atom of chlorosilanes – with fluoromethyllithium (LiCH2F) – as a general strategy for their direct preparation. The procedure - exhibiting remarkable dependance on steric elements across silicon – can be advantageously extended to prepare distinct IV-row heteroatom-centered analogues such as tin and germanium organometallics.
2026
1
5
carbanions; fluoromethylation; nucleophilic substitution; organofluorine chemistry; silanes
Nardi, Alberto; Castiglione, Davide; Miele, Margherita; Castoldi, Laura; Pace, Vittorio
File in questo prodotto:
File Dimensione Formato  
Eur J Org Chem - 2026 - Nardi - Preparation of ‐Mono‐Fluoromethyl Silanes via Nucleophilic Displacement on Chlorosilanes (1).pdf

Accesso aperto

Dimensione 643.27 kB
Formato Adobe PDF
643.27 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/2136293
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 0
  • ???jsp.display-item.citation.isi??? 0
social impact