Custom-Made Pyrene Photocatalyst-Promoted Desulfonylation of Arylethenyl Sulfones Using Green-Light-Emitting Diodes

Abstract

The Sonogashira coupling of 1,3,6,8-tetrabromopyrene with 4-[(–)-β-citronellyloxy]phenylethyne was employed to synthesize 1,3,6,8-tetra[4-(citronellyloxy)phenylethynyl]pyrene. The pyrene derivative catalyzed the reductive desulfonylation of ethenyl sulfones via visible-light irradiation (514 nm green light-emitting diodes) in the presence of i-Pr₂NEt. The β-citronellyloxy groups provided the sufficient solubility to the highly π-expanded pyrene catalyst, and their polar oxygen functionalities enabled the easy separation of the catalyst from the products via column chromatography.

Keywords

desulfonylation - photocatalyst - pyrene - ethenyl sulfones - ethenes - green LED

Publication History

Received: 06 January 2021

Accepted after revision: 25 January 2021

Article published online:
22 February 2021

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