Supported Eosin Y as a Photocatalyst for C-H Arylation of Furan in Batch and Flow

Molecules. 2022 Aug 10;27(16):5096. doi: 10.3390/molecules27165096.

Abstract

Eosin Y is one of the most popular organic dyes used as a photoredox catalyst and is largely employed in photochemical reactions both as a homogeneous and heterogeneous photocatalyst after immobilization. Immobilization of Eosin Y onto a solid support has many advantages, such as the possibility of recovery and reuse of the photocatalyst and the possibility of its use under flow conditions. In this paper, we report our findings on the immobilization of Eosin Y onto Merrifield resin and its application in the direct photochemical arylation of furan with aryldiazonium salts. The synthesized supported photocatalyst was used in batch reactions under heterogeneous conditions with different aryl diazonium salts, and its recovery and recycle were demonstrated for up to three times. The immobilized photocatalyst was then loaded in a packed-bed reactor and used under continuous flow conditions. The flow reaction allowed the arylated products to be obtained with higher productivity and space-time-yield than the batch in a very short reaction time.

Keywords: continuous flow photochemistry; eosin Y; green chemistry; photocatalysis; supported catalysis.

MeSH terms

  • Catalysis
  • Eosine Yellowish-(YS)
  • Furans*
  • Salts*

Substances

  • Furans
  • Salts
  • Eosine Yellowish-(YS)

Grants and funding

Financial support from MUR for the project PRIN 2017 “SURSUMCAT” (PRIN 2017 ID: 20174SYJAF) and from Università degli Studi di Milano (grant PSR 2020) is gratefully acknowledged.