Visible-light-mediated minisci C–H alkylation of heteroarenes with 4-alkyl-1,4-dihydropyridines using O2 as an oxidant

Herein, we report a protocol for direct visible-light-mediated Minisci C–H alkylation reactions of N-heteroarenes with 4-alkyl-1,4-dihydropyridines at room temperature with molecular oxygen as an oxidant. The protocol permits efficient functionalization of various N-heteroarenes with a broad range o...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2020-01, Vol.22 (17), p.5599-5604
Main Authors: Dong, Jianyang, Fuyang Yue, Xu, Wentao, Song, Hongjian, Liu, Yuxiu, Wang, Qingmin
Format: Article
Language:English
Subjects:
Alkylation
Green chemistry
Natural products
Nitrogen
Oxidants
Oxidizing agents
Oxygen
Room temperature
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Summary:Herein, we report a protocol for direct visible-light-mediated Minisci C–H alkylation reactions of N-heteroarenes with 4-alkyl-1,4-dihydropyridines at room temperature with molecular oxygen as an oxidant. The protocol permits efficient functionalization of various N-heteroarenes with a broad range of cyclic and acyclic primary, secondary, and tertiary alkyl groups and is scalable to the gram level. This mild protocol uses an inexpensive, green oxidant and is suitable for late-stage C–H alkylation of complex nitrogen-containing molecules. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.
ISSN:1463-9262
1463-9270
DOI:10.1039/d0gc02111c