Photoredox-Catalyzed N-Directed Regioselective Difluoroalkylation of Unactivated C(sp3)-H Bonds

被引：19

作者：

Chen, Xi ^{[1
]}

Zhang, Zhe ^{[1
]}

Shi, Wei-Yu ^{[1
]}

Ding, Ya-Nan ^{[1
]}

Luan, Yu-Yong ^{[1
]}

Huang, Yan-Chong ^{[1
]}

Wang, Qiang ^{[2
]}

Liu, Xue-Yuan ^{[1
]}

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, Sch Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Dongguan Univ Technol, Coll Chem Engn & Energy Technol, Guangdong Prov Key Lab Distributed Energy Syst, Dongguan 523808, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 24期

基金：

中国国家自然科学基金;

关键词：

ENOL SILYL ETHERS; C-H BONDS; MANNICH REACTION; DIFLUOROENOXYSILANES; FUNCTIONALIZATION; ALKYLATION; INHIBITORS; FLUORINE; AMINES;

D O I：

10.1021/acs.orglett.3c01361

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a redox-neutral, visible-light-mediated difluoroalkylationof unactivated C(sp(3))-H bonds in amides via nitrogen-centeredradicals triggered intramolecular hydrogen atom transfer. Notably,all types (tertiary, secondary, and primary) of gamma-C(sp(3))-H bonds displayed excellent reactivity. This methodologypresents a facile route for the regioselective introduction of alpha,alpha-difluoroketonefragments into organic molecules. Moreover, the resulting gem-difluoroketones can be readily converted to structurallydiverse difluoro-containing molecules, offering broad potential applicationsin medicinal chemistry and chemical biology.

引用

页码：4456 / 4461

页数：6