N,N,N',N'-Tetramethylethylenediamine-Enabled PhotoredoxCatalyzed C-H Methylation of N-Heteroarenes

被引：20

作者：

Liu, Fang ^{[1
]}

Ye, Zhi-Peng ^{[1
]}

Hu, Yuan-Zhuo ^{[1
]}

Gao, Jie ^{[1
]}

Zheng, Lan ^{[1
]}

Chen, Kai ^{[1
,2
]}

Xiang, Hao-Yue ^{[1
]}

Chen, Xiao-Qing ^{[1
,3
]}

Yang, Hua ^{[1
,3
]}

机构：

[1] Cent South Univ, Coll Chem & Chem Engn, Changsha 410083, Peoples R China

[2] Peking Univ, Key Lab Chem Oncogen, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

[3] Cent South Univ, Key Lab Hunan Prov Water Environm & Agr Prod Safe, Changsha 410083, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 17期

基金：

中国国家自然科学基金;

关键词：

PHOTOINDUCED METHYLATION; CATALYZED METHYLATION; CARBOXYLIC-ACIDS; DNA METHYLATION; OXIDATION; ALKYLATION; QUINOXALIN-2(1H)-ONES; PEROXIDE; CLEAVAGE; DERIVATIVES;

D O I：

10.1021/acs.joc.1c01325

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aiming at the valuable methylation process, readily available and inexpensive N, N, N', N'- tetramethylethylenediamine (TMEDA) was first identified as a new methyl source in photoredox-catalyzed transformation in this work. By virtue of this simple methylating reagent, a facile and practical protocol for the direct C-H methylation of N-heteroarenes was developed, featuring mild reaction conditions, broad substrate scope, and scalability. Mechanistic studies disclosed that a sequential photoredox, base-assisted proton shift, fragmentation, and tautomerization process was essentially involved.

引用

页码：11905 / 11914

页数：10

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