106662-18-4Relevant articles and documents
Electrophotocatalytic Decarboxylative C?H Functionalization of Heteroarenes
Lai, Xiao-Li,Shu, Xiao-Min,Song, Jinshuai,Xu, Hai-Chao
, p. 10626 - 10632 (2020)
Decarboxylative C?H functionalization reactions are highly attractive methods for forging carbon–carbon bonds considering their inherent step- and atom-economical features and the pervasiveness of carboxylic acids and C?H bonds. An ideal approach to achieve these dehydrogenative transformations is through hydrogen evolution without using any chemical oxidants. However, effective couplings by decarboxylative carbon–carbon bond formation with proton reduction remain an unsolved challenge. Herein, we report an electrophotocatalytic approach that merges organic electrochemistry with photocatalysis to achieve the efficient direct decarboxylative C?H alkylation and carbamoylation of heteroaromatic compounds through hydrogen evolution. This electrophotocatalytic method, which combines the high efficiency and selectivity of photocatalysis in promoting decarboxylation with the superiority of electrochemistry in effecting proton reduction, enables the efficient coupling of a wide range of heteroaromatic bases with a variety of carboxylic acids and oxamic acids. Advantageously, this method is scalable to decagram amounts, and applicable to the late-stage functionalization of drug molecules.
C-H alkylation of heteroarenes with alkyl oxalates by molecular photoelectrocatalysis
Xu, Fan,Lai, Xiao-Li,Xu, Hai-Chao
, p. 369 - 372 (2021)
An oxidant- and metal-free photoelectrocatalytic C-H alkylation reaction of heteroarenes with alkyl oxalates has been developed. Several classes of heteroaromatics, such as quinolines, isoquinolines, pyridines, and phenanthridines, can be alkylated with t
Direct Arylation of Unactivated Alkanes with Heteroarenes by Visible-Light Catalysis
Huang, Cheng,Wang, Jing-Hao,Qiao, Jia,Fan, Xiu-Wei,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
, p. 12904 - 12912 (2019)
The functionalization of aliphatic C-H bonds is both a major challenge and a desirable goal in organic synthesis. Here, we describe the successful arylation of unactivated alkanes with heteroarenes by using iridium polypyridyl complexes as the photocatalyst and persulfate as the HAT catalyst precursor under visible-light irradiation. This reaction features good functional group tolerance and broad scope with regard to both alkane and heteroarene substrates (37 examples), which allows direct access to alkyl-substituted N-heteroarenes, a key structural motif in natural products and bioactive molecules.
Late-Stage Alkylation of N-Containing Heteroarenes Enabled by Homolysis of Alkyl-1,4-dihydropyridines under Blue LED Irradiation
Chen, Xiaoping,Luo, Xiaosheng,Wang, Kaiqian,Liang, Feng,Wang, Ping
, p. 733 - 737 (2021)
Alkylated heteroarenes are widely found in bioactive molecules and pharmaceuticals. Therefore, there is great interest in developing a chemoselective alkylation of heteroarenes under mild conditions, particularly during a late-stage functionalization step for the purpose of rapid derivatization. Herein, we introduce an efficient visible-light-promoted C-H alkylation of nitrogen-containing heteroarenes by using C4-Alkyl 1,4-dihydropyridines (DHPs) as radical precursors at ambient temperatures. A broad scope of heteroarenes, such as 4-hydroxyquinazoline and its derivatives, including those bearing electron-donating or electron-withdrawing groups, can be successfully alkylated in good yields by using various C4-Alkyl DHPs.
Development of a Quinolinium/Cobaloxime Dual Photocatalytic System for Oxidative C-C Cross-Couplings via H2Release
Li, Jianbin,Huang, Chia-Yu,Han, Jing-Tan,Li, Chao-Jun
, p. 14148 - 14158 (2021/11/27)
Designing molecular photocatalysts for potent photochemical reactivities ranks among the most challenging but rewarding endeavors in synthetic photochemistry. Herein, we document a quinoline-based organophotoredox catalyst, 2,4-bis(4-methoxyphenyl)quinoli
