Sustainable and efficient aryl halides with copper free Heck−Cassar−Sonogashira (HCS) and Suzuki−Miyaura (SM) cross-coupling reactions were described. Independently from the aryl chloride substituents, the green protocol based on N-hydroxyethylpyrrolidone (HEP)/water as solvents and sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl-3-sulfonate (sSPhos) as ligand afforded the target products with a high turnover number (TON), high reaction mass efficiency (RME), and low process mass intensity (PMI). The best results have been obtained with TMG and Cs2CO3 as the base for the HCS and Cs2CO3 and K2CO3 for the SM coupling. The PMI and RME achieved are among the best in the field and allowed us to simplify purification processes that are critical for industrial applications.

Copper-Free Heck−Cassar−Sonogashira and Suzuki−Miyaura Reactions of Aryl Chlorides: A Sustainable Approach

Chiara Palladino;Tommaso Fantoni
;
Lucia Ferrazzano;Alessandra Tolomelli;Walter Cabri
2023

Abstract

Sustainable and efficient aryl halides with copper free Heck−Cassar−Sonogashira (HCS) and Suzuki−Miyaura (SM) cross-coupling reactions were described. Independently from the aryl chloride substituents, the green protocol based on N-hydroxyethylpyrrolidone (HEP)/water as solvents and sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl-3-sulfonate (sSPhos) as ligand afforded the target products with a high turnover number (TON), high reaction mass efficiency (RME), and low process mass intensity (PMI). The best results have been obtained with TMG and Cs2CO3 as the base for the HCS and Cs2CO3 and K2CO3 for the SM coupling. The PMI and RME achieved are among the best in the field and allowed us to simplify purification processes that are critical for industrial applications.
2023
Chiara Palladino, Tommaso Fantoni, Lucia Ferrazzano, Alessandra Tolomelli, Walter Cabri
File in questo prodotto:
File Dimensione Formato  
2023 ACS SustainableChem.Eng.2023,11, 15994−16004.pdf

accesso aperto

Tipo: Versione (PDF) editoriale
Licenza: Licenza per Accesso Aperto. Creative Commons Attribuzione (CCBY)
Dimensione 3.89 MB
Formato Adobe PDF
3.89 MB Adobe PDF Visualizza/Apri
sc3c04926_si_001.pdf

accesso aperto

Tipo: File Supplementare
Licenza: Licenza per Accesso Aperto. Creative Commons Attribuzione (CCBY)
Dimensione 6.11 MB
Formato Adobe PDF
6.11 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/11585/949874
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 0
  • ???jsp.display-item.citation.isi??? 0
social impact