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

doi:10.6023/cjoc202006075

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

钯催化芳香溴化物与三甲基硅基重氮甲烷的还原偶联及其在芳香化合物甲基化中的应用

王帅, 杨成, 孙硕, 孙晗力, 王剑波

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 E-mail:wangjb@pku.edu.cn
基金资助:
国家自然科学基金（No.91956104）资助项目.

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

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).

1. cjoc202006075.pdf(3401KB)

Abstract

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

Cite this article

Wang Shuai, Yang Cheng, Sun Shuo, Sun Hanli, Wang Jianbo. Palladium-Catalyzed Reductive Coupling of Aromatic Bromides and Trimethylsilyldiazomethane: Its Application to Methylation of Aromatic Compounds[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3881-3888.

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钯催化芳香溴化物与三甲基硅基重氮甲烷的还原偶联及其在芳香化合物甲基化中的应用

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

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