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

页码：4394 / 4399

页数：6

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