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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 9: 2914 - 2924

DOI: https://doi.org/10.6023/cjoc202204043

ARTICLES

Transition Metal-Free Selective Aerobic C-Alkylation of Methyl N-Heteroarenes with Alcohols

  • Tianyu Chen ,
  • Feng Han ,
  • Shuangyan Li ,
  • Jianping Liu ,
  • Jianhui Chen ,
  • Qing Xu
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  • College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035
* Corresponding authors. E-mail: ;

Received date: 2022-04-16

  Revised date: 2022-05-19

  Online published: 2022-06-09

Supported by

National Natural Science Foundation of China(21672163); Natural Science Foundation of Zhejiang Province for Distinguished Young Scholars(LR14B020002)

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Abstract

By performing the reaction under air using a suitable base, selective C-alkylation of methyl N-heteroarenes with various alcohols can be effectively achieved without using any external catalyst. Control experiments reveal that transition metal catalysts are indeed not needed in the reaction. Mechanistic studies reveal that base and air can play crucial roles, so that the reaction is in effect initiated by base-promoted aerobic oxidation of the alcohols to carbonyl intermediates, which can then catalyze the C-alkylation reaction to selectively afford the alkylated N-heteroarenes, and be regenerated and recovered to furnish the catalytic cycle. This method has obvious advantages of broad substrate scope, requiring no transition metal catalysts/ligands and inert conditions, simple operation, low cost, no transition metal residue contaminant in the products, and is thus a practical way for functionalization of the N-heteroarene compounds.

Key words： alcohols; alkylation; methyl N-heteroarenes; transition metal-free

Cite this article

Tianyu Chen , Feng Han , Shuangyan Li , Jianping Liu , Jianhui Chen , Qing Xu . Transition Metal-Free Selective Aerobic C-Alkylation of Methyl N-Heteroarenes with Alcohols[J]. Chinese Journal of Organic Chemistry, 2022 , 42(9) : 2914 -2924 . DOI: 10.6023/cjoc202204043

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