A visible-light mediated three-component radical process using dithiocarbamate anion catalysis

被引：45

作者：

Cuadros, Sara ^{[1
]}

Horwitz, Matthew A. ^{[1
]}

Schweitzer-Chaput, Bertrand ^{[1
]}

Melchiorre, Paolo ^{[1
,2
,3
]}

机构：

[1] Barcelona Inst Sci & Technol, ICIQ Inst Chem Res Catalonia, Ave Paisos Catalans 16, Tarragona 43007, Spain

[2] IIT, Lab Asymmetr Catalysis & Photochem, Via Morego 30, I-16163 Genoa, Italy

[3] ICREA Catalan Inst Res & Adv Studies, Passeig Lluis Co 23, Barcelona 08010, Spain

来源：

CHEMICAL SCIENCE | 2019年 / 10卷 / 21期

基金：

欧洲研究理事会;

关键词：

PHOTOREDOX CATALYSIS; CHEMISTRY; PYRROLES;

D O I：

10.1039/c9sc00833k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a photoinduced three-component radical process, which couples readily available alkyl chlorides, maleimides, and heteroaromatic fragments to rapidly generate complex chiral products with high diastereocontrol. This method generates radicals via an S(N)2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the precursors. It therefore grants access to open-shell intermediates from substrates that would be incompatible with or inert to classical radical-generating strategies. The redox-neutral conditions of this process make it tolerant of redox-sensitive substrates and allow the installation of multiple biologically relevant heterocycles within the cascade products.

引用

页码：5484 / 5488

页数：5

共 41 条

[1] TANDEM NUCLEOPHILIC AND RADICAL CHEMISTRY IN THE REPLACEMENT OF THE HYDROXYL GROUP BY A CARBON CARBON BOND - A CONCISE SYNTHESIS OF SHOWDOMYCIN [J].