Selective N-α-C-H alkylation of cyclic tertiary amides via visible-light-mediated 1,5-hydrogen atom transfer

被引：21
|
作者：
Wang, Junlei [1 ]
Xie, Qinglin [1 ]
Gao, Guocheng [1 ]
Li, Hongqing [1 ]
Lu, Wenyun [1 ]
Cai, Xiaodong [1 ]
Chen, Xuemei [1 ]
Huang, Binbin [2 ,3 ]
机构：
[1] Guizhou Minzu Univ, Sch Chem Engn, Guiyang 550000, Peoples R China
[2] Beijing Normal Univ, Coll Educ Future, Zhuhai 519087, Peoples R China
[3] Beijing Normal Univ, Coll Arts & Sci, Zhuhai 519087, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 17期
基金：
中国国家自然科学基金;
关键词：
C-H BONDS; ALPHA-AMINO RADICALS; PHOTOREDOX CATALYSIS; DESATURATION; ARYLATION; HYDROAMINOALKYLATION; ADDITIONS; MILD;
D O I：
10.1039/d3qo00914a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report an effective C-H bond activation-alkylation strategy for 2-iodobenzoyl protected cyclic amines at the N-& alpha;-position through a visible-light mediated 1,5-hydrogen atom transfer (HAT) process. The readily reducible C-Ar-I bond was selected as an appropriate precursor to generate aryl radicals, which would further trigger an intramolecular HAT process to access the key N-& alpha;-radicals. Scale-up reaction and several examples of late-stage functionalization on structurally complex bio-active molecules demonstrate the synthetic potential of this protocol.
引用
收藏
页码：4394 / 4399
页数：6
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