Photoinduced Site-Selective Functionalization of Aliphatic C–H Bonds by Pyridine N‑oxide Based HAT Catalysts

Readily available and facilely tunable pyridine N-oxides have been developed as effective photoinduced hydrogen-atom-transfer (HAT) catalysts for site-selective C–H functionalizations of a broad range of C–H substrates, including unactivated alkanes. Pyridine N-oxide radicals, catalytically generate...

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Bibliographic Details
Published in:ACS catalysis 2022-08, Vol.12 (16), p.10441-10448
Main Authors: Wang, Ban, Ascenzi Pettenuzzo, Cristina, Singh, Jujhar, Mccabe, Gavin E., Clark, Logan, Young, Ryan, Pu, Jingzhi, Deng, Yongming
Format: Article
Language:English
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Summary:Readily available and facilely tunable pyridine N-oxides have been developed as effective photoinduced hydrogen-atom-transfer (HAT) catalysts for site-selective C–H functionalizations of a broad range of C–H substrates, including unactivated alkanes. Pyridine N-oxide radicals, catalytically generated from N-oxides by photoredox catalyzed single-electron oxidation, are the key intermediates that enable an effective HAT process for carbon radical generation to achieve alkylation, amination, azidation, allylation, and cyanation. Additionally, the fine-tuning of reactivity and selectivity of pyridine N-oxides through operationally simple structural modification was investigated and showed promising capability for selective functionalization of unactivated C­(sp3)–H bonds.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.2c02993