Carrying out photoredox direct arylation couplings between aryl halides and aryls in aqueous solutions of surfactants enables unprecedented selectivity with respect to the competing dehalogenation process, thanks to the partition coefficient of the selected sacrificial base. The use of a microfluidic reactor dramatically improves the reaction time, without eroding the yields and selectivity. The design of a metal free sensitizer, which also acts as the surfactant, sizeably improves the overall sustainability of arylation reactions and obviates the need for troublesome purification from traces of metal catalysts. The generality of the method is investigated over a range of halides carrying a selection of electron withdrawing and electron donating substituents.

Pallini, F., Sangalli, E., Sassi, M., Roth, P., Mattiello, S., & Beverina, L. (2021). Selective photoredox direct arylations of aryl bromides in water in a microfluidic reactor. ORGANIC & BIOMOLECULAR CHEMISTRY, 19(13), 3016-3023 [10.1039/d1ob00050k].

Selective photoredox direct arylations of aryl bromides in water in a microfluidic reactor

Pallini F.;Sassi M.;Mattiello S.
;
Beverina L.
2021

Abstract

Carrying out photoredox direct arylation couplings between aryl halides and aryls in aqueous solutions of surfactants enables unprecedented selectivity with respect to the competing dehalogenation process, thanks to the partition coefficient of the selected sacrificial base. The use of a microfluidic reactor dramatically improves the reaction time, without eroding the yields and selectivity. The design of a metal free sensitizer, which also acts as the surfactant, sizeably improves the overall sustainability of arylation reactions and obviates the need for troublesome purification from traces of metal catalysts. The generality of the method is investigated over a range of halides carrying a selection of electron withdrawing and electron donating substituents.
Articolo in rivista - Articolo scientifico
photochemistry; flow chemistry; green chemistry;
English
3016
3023
8
Pallini, F., Sangalli, E., Sassi, M., Roth, P., Mattiello, S., & Beverina, L. (2021). Selective photoredox direct arylations of aryl bromides in water in a microfluidic reactor. ORGANIC & BIOMOLECULAR CHEMISTRY, 19(13), 3016-3023 [10.1039/d1ob00050k].
Pallini, F; Sangalli, E; Sassi, M; Roth, P; Mattiello, S; Beverina, L
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/10281/318800
Citazioni
  • Scopus 4
  • ???jsp.display-item.citation.isi??? 5
Social impact