Late-Stage Alkylation of N-Containing Heteroarenes Enabled by Homolysis of Alkyl-1,4-dihydropyridines under Blue LED Irradiation

Abstract Alkylated heteroarenes are widely found in bioactive molecules and pharmaceuticals. Therefore, there is great interest in developing a chemoselective alkylation of heteroarenes under mild conditions, particularly during a late-stage functionalization step for the purpose of rapid derivatiza...

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Bibliographic Details
Published in:Synlett 2021-04, Vol.32 (7), p.733-737
Main Authors: Chen, Xiaoping, Luo, Xiaosheng, Wang, Kaiqian, Liang, Feng, Wang, Ping
Format: Article
Language:English
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Summary:Abstract Alkylated heteroarenes are widely found in bioactive molecules and pharmaceuticals. Therefore, there is great interest in developing a chemoselective alkylation of heteroarenes under mild conditions, particularly during a late-stage functionalization step for the purpose of rapid derivatization. Herein, we introduce an efficient visible-light-promoted C–H alkylation of nitrogen-containing heteroarenes by using C4-alkyl 1,4-dihydropyridines (DHPs) as radical precursors at ambient temperatures. A broad scope of heteroarenes, such as 4-hydroxyquinazoline and its derivatives, including those bearing electron-donating or electron-withdrawing groups, can be successfully alkylated in good yields by using various C4-alkyl DHPs.
ISSN:0936-5214
1437-2096
DOI:10.1055/a-1294-0158