CdS Quantum Dots for Metallaphotoredox-Enabled Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides

Semiconductor quantum dots (QDs) offer many advantages as photocatalysts for synthetic photoredox catalysis, but no reports have explored the use of QDs with nickel catalysts for C–C bond formation. We show here that 5.7 nm CdS QDs are robust photocatalysts for photoredox-promoted cross-electrophile...

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Bibliographic Details
Published in:ACS catalysis 2023-07, Vol.13 (13), p.9018-9024
Main Authors: Mouat, Julianna M., Widness, Jonas K., Enny, Daniel G., Meidenbauer, Mahilet T., Awan, Farwa, Krauss, Todd D., Weix, Daniel J.
Format: Article
Language:English
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Summary:Semiconductor quantum dots (QDs) offer many advantages as photocatalysts for synthetic photoredox catalysis, but no reports have explored the use of QDs with nickel catalysts for C–C bond formation. We show here that 5.7 nm CdS QDs are robust photocatalysts for photoredox-promoted cross-electrophile coupling (turnover number (TON) up to 40,000). These conditions can be utilized on a small scale (96-well plate) or adapted to flow. NMR studies show that triethanolamine (TEOA)-capped QDs are the active catalyst and that TEOA can displace native phosphonate and carboxylate ligands, demonstrating the importance of the QD surface chemistry.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.3c01984