Light-Induced Sonogashira C–C Coupling under Mild Conditions Using Supported Palladium Nanoparticles

Elhage, Ayda; Lanterna, Anabel E.; Scaiano, Juan C.

Abstract

The Sonogashira reaction can easily be photocatalyzed by supported palladium nanoparticles. Herein, we demonstrate that the direct excitation of PdNPs can catalyze the C–C coupling between different aryl iodides and acetylenes under very mild conditions in short reaction times. The catalyst is air- and moisture-tolerant and can be supported on a wide range of materials, including inert ones such as nanodiamonds. Study of the action spectrum demonstrates that direct excitation of the PdNPs is required, and in the case of Pd@TiO2, for example, visible excitation works well whereas UVA (368 nm) irradiation is ineffective because of TiO2 shielding the Pd absorption. The catalyst can be reused a couple of times, but when it loses activity, it can be readily reactivated by a simple reductive photochemical strategy.

• Journal Article Type: Article
• Acceptance Date: Nov 6, 2017
• Online Publication Date: Jan 3, 2018
• Publication Date: Feb 5, 2018
• Deposit Date: Jun 22, 2020
• Publicly Available Date: Jul 21, 2020
• Journal: ACS Sustainable Chemistry & Engineering
• Electronic ISSN: 2168-0485
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 6
• Issue: 2
• Pages: 1717-1722
• DOI: https://doi.org/10.1021/acssuschemeng.7b02992
• Public URL: https://nottingham-repository.worktribe.com/output/4442705
• Publisher URL: https://pubs.acs.org/doi/10.1021/acssuschemeng.7b02992
• Additional Information: Copyright © 2017 American Chemical Society