A direct nucleophilic monofluoroalkylation strategy leveraging on lithium fluorocarbenoids has been developed. Flow microreactor technology allows capitalization of the synthetic potential of these scarcely explored short-lived intermediates – namely 1-fluoro-2-phenylethyllithium, 1-fluoro-3-phenylpropyllithium, and 1-fluorononyllithium – generated through lithium/iodine exchange reaction. This robust protocol was employed to prepare new fluorinated products, adopting various classes of electrophiles. The inherent advantages of microreactor technology contribute to rendering this approach a new valuable tool for direct fluoroalkylation chemistry.

Unlocking geminal fluorohaloalkanes in nucleophilic fluoroalkylation chemistry: generation and trapping of lithiumfluorocarbenoids enabled by flow microreactors

Mauro Spennacchio
Membro del Collaboration Group
;
Marco Colella
Writing – Original Draft Preparation
;
Michael Andresini
Membro del Collaboration Group
;
Elena Graziano
Membro del Collaboration Group
;
Leonardo Degennaro
Supervision
;
Renzo Luisi
Writing – Review & Editing
2023-01-01

Abstract

A direct nucleophilic monofluoroalkylation strategy leveraging on lithium fluorocarbenoids has been developed. Flow microreactor technology allows capitalization of the synthetic potential of these scarcely explored short-lived intermediates – namely 1-fluoro-2-phenylethyllithium, 1-fluoro-3-phenylpropyllithium, and 1-fluorononyllithium – generated through lithium/iodine exchange reaction. This robust protocol was employed to prepare new fluorinated products, adopting various classes of electrophiles. The inherent advantages of microreactor technology contribute to rendering this approach a new valuable tool for direct fluoroalkylation chemistry.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

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/11586/428501
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? 2
  • Scopus 5
  • ???jsp.display-item.citation.isi??? 7
social impact