A straightforward flow synthesis of α-chloro aldehydes has been developed. The strategy involves, for the first time, the thermal unstable chloroiodomethyllithium carbenoid and carbonyl compounds. A batch versus flow comparative study showcases the superb capability of flow technology in prolonging the lifetime of the lithiated carbenoid, even at -20 °C. Remarkably, the high chemoselectivity realized in flow allowed for preparing polyfunctionalized α-chloro aldehydes not easily accessible with traditional batch procedures.

Flow Microreactor Technology for Taming Highly Reactive Chloroiodomethyllithium Carbenoid: Direct and Chemoselective Synthesis of α-Chloroaldehydes / Musci, Pantaleo; Colella, Marco; Sivo, Alessandra; Romanazzi, Giuseppe; Luisi, Renzo; Degennaro, Leonardo. - In: ORGANIC LETTERS. - ISSN 1523-7052. - ELETTRONICO. - 22:9(2020), pp. 3623-3627. [10.1021/acs.orglett.0c01085]

Flow Microreactor Technology for Taming Highly Reactive Chloroiodomethyllithium Carbenoid: Direct and Chemoselective Synthesis of α-Chloroaldehydes

Giuseppe Romanazzi;
2020-01-01

Abstract

A straightforward flow synthesis of α-chloro aldehydes has been developed. The strategy involves, for the first time, the thermal unstable chloroiodomethyllithium carbenoid and carbonyl compounds. A batch versus flow comparative study showcases the superb capability of flow technology in prolonging the lifetime of the lithiated carbenoid, even at -20 °C. Remarkably, the high chemoselectivity realized in flow allowed for preparing polyfunctionalized α-chloro aldehydes not easily accessible with traditional batch procedures.
2020
lettera
Flow Microreactor Technology for Taming Highly Reactive Chloroiodomethyllithium Carbenoid: Direct and Chemoselective Synthesis of α-Chloroaldehydes / Musci, Pantaleo; Colella, Marco; Sivo, Alessandra; Romanazzi, Giuseppe; Luisi, Renzo; Degennaro, Leonardo. - In: ORGANIC LETTERS. - ISSN 1523-7052. - ELETTRONICO. - 22:9(2020), pp. 3623-3627. [10.1021/acs.orglett.0c01085]
File in questo prodotto:
File Dimensione Formato  
2020_Flow_Microreactor_Technology_for_Taming_Highly_Reactive_Chloroiodomethyllithium_Carbenoid_pdfeditoriale.pdf

Solo utenti POLIBA

Tipologia: Versione editoriale
Licenza: Tutti i diritti riservati
Dimensione 1.57 MB
Formato Adobe PDF
1.57 MB 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/11589/196000
Citazioni
  • Scopus 50
  • ???jsp.display-item.citation.isi??? 43
social impact