Photocatalytic alkenes to ring-fused quinazolin-4(3H)-ones via proton-transfer shuttle using TFA

Herein, a novel metal-free photocatalytic system is reported that enables intramolecular hydroarylation of unactivated alkenes via a proton transfer shuttle using TFA, providing a concise access to the formation of pyrroloquinazolinone and pyridyquinazolinone products in moderate to good yields. Mec...

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Bibliographic Details
Published in:Tetrahedron 2024-05, Vol.158, p.133990, Article 133990
Main Authors: Wang, Xianming, Li, Xinhan, Zou, Luqian, Lu, Qinli, Zao, Chenggang, Ou, Qingling, Fan, Ruifeng, Xu, Jianbin, Fan, Baomin
Format: Article
Language:English
Subjects:
alkenes
cyclization reactions
photocatalysis
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Summary:Herein, a novel metal-free photocatalytic system is reported that enables intramolecular hydroarylation of unactivated alkenes via a proton transfer shuttle using TFA, providing a concise access to the formation of pyrroloquinazolinone and pyridyquinazolinone products in moderate to good yields. Mechanistic studies revealed that the protonated quinazolinone is the key radical precursor mediating the intramolecular cyclization reaction. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2024.133990