Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (9): 2914-2924.DOI: 10.6023/cjoc202204043 Previous Articles     Next Articles



陈天煜, 韩峰, 李双艳, 刘建平, 陈建辉*(), 徐清*()   

  1. 温州大学化学与材料工程学院 浙江温州 325035
  • 收稿日期:2022-04-16 修回日期:2022-05-19 发布日期:2022-06-08
  • 通讯作者: 陈建辉, 徐清
  • 基金资助:
    国家自然科学基金(21672163); 浙江省自然科学基金杰出青年基金(LR14B020002)

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()   

  1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035
  • Received:2022-04-16 Revised:2022-05-19 Published:2022-06-08
  • Contact: Jianhui Chen, Qing Xu
  • Supported by:
    National Natural Science Foundation of China(21672163); Natural Science Foundation of Zhejiang Province for Distinguished Young Scholars(LR14B020002)

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