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
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
收藏
页码:5484 / 5488
页数:5
相关论文
共 41 条
[21]  
Liautard V, 2015, MULTICOMPONENT REACTIONS IN ORGANIC SYNTHESIS, P401
[22]   Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development [J].
Matsui, Jennifer K. ;
Lang, Simon B. ;
Heitz, Drew R. ;
Molander, Gary A. .
ACS CATALYSIS, 2017, 7 (04) :2563-2575
[23]   Cascade reactions in total synthesis [J].
Nicolaou, K. C. ;
Edmonds, David J. ;
Bulger, Paul G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) :7134-7186
[24]   Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids [J].
O'Hagan, D .
NATURAL PRODUCT REPORTS, 2000, 17 (05) :435-446
[25]   Heteroaromatic Rings of the Future [J].
Pitt, William R. ;
Parry, David M. ;
Perry, Benjamin G. ;
Groom, Colin R. .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (09) :2952-2963
[26]   Radical cascade reactions triggered by single electron transfer [J].
Plesniak, Mateusz P. ;
Huang, Huan-Ming ;
Procter, David J. .
NATURE REVIEWS CHEMISTRY, 2017, 1 (10)
[27]   Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis [J].
Prier, Christopher K. ;
Rankic, Danica A. ;
MacMillan, David W. C. .
CHEMICAL REVIEWS, 2013, 113 (07) :5322-5363
[28]  
Quiclet-Sire M, 2008, ORG LETT, V10, P3279, DOI [10.1021/lo801162m, 10.1021/ol801162m]
[29]   Experimental and Calculated Electrochemical Potentials of Common Organic Molecules for Applications to Single-Electron Redox Chemistry [J].
Roth, Hudson G. ;
Romero, Nathan A. ;
Nicewicz, David A. .
SYNLETT, 2016, 27 (05) :714-723
[30]   Radical-mediated three-component coupling of alkenes [J].
Schaffner, Arnaud Pierre ;
Sarkunam, Kandhasamy ;
Renaud, Philippe .
HELVETICA CHIMICA ACTA, 2006, 89 (10) :2450-2461