Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3881-3888.DOI: 10.6023/cjoc202006075 Previous Articles     Next Articles

Special Issue: 有机硅化学虚拟合辑 创刊四十周年专辑


王帅, 杨成, 孙硕, 孙晗力, 王剑波   

  1. 北京大学化学与分子工程学院 生物有机与分子工程教育部重点实验室 北京 100871
  • 收稿日期:2020-06-30 修回日期:2020-07-19 发布日期:2020-08-06
  • 通讯作者: 王剑波
  • 基金资助:

Palladium-Catalyzed Reductive Coupling of Aromatic Bromides and Trimethylsilyldiazomethane: Its Application to Methylation of Aromatic Compounds

Wang Shuai, Yang Cheng, Sun Shuo, Sun Hanli, Wang Jianbo   

  1. Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871
  • Received:2020-06-30 Revised:2020-07-19 Published:2020-08-06
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 91956104).

The introduction of methyl group into aromatic compounds is a valuable transformation. A large number of known methods use organohalides as the starting materials. However, those methods require pre-synthesized methyl metal reagents or toxic methyl electrophiles. Herein, a palladium-catalyzed reductive coupling reaction between aryl bromides and trimethylsilyl-diazomethane is developed, and the following desilicification process can afford the methylated products. This transformation has broad functional group tolerance and allows methylation of (hetero)aryl halides in moderate to good yields. Thus, it has the potential to be an attractive approach for methylation of organic. In addition, this reductive coupling can also serve as an efficient way for the introduction of silylmethyl group.

Key words: methylation, trimethylsilyldiazomethane, metal carbene, migratory insertion, reductive coupling