Dual Photoredox/Nickel-Catalyzed Three-Component Carbofunctionalization of Alkenes

被引:152
作者
Garcia-Dominguez, Andres [1 ]
Mondal, Rahul [1 ]
Nevado, Cristina [1 ]
机构
[1] Univ Zurich, Dept Chem, Winterthurerstr 190, CH-8057 Zurich, Switzerland
基金
瑞士国家科学基金会; 欧洲研究理事会;
关键词
alkenes; multicomponent reactions; nickel; photochemistry; reaction mechanisms; CROSS-COUPLING REACTIONS; CARBONYL ALKYL BROMIDES; INTERMOLECULAR TRIFLUOROMETHYLARYLATION; SULFONATED OXINDOLES; RADICAL GENERATION; NICKEL CATALYSIS; SULFINATE SALTS; ARYL BROMIDES; ONE-POT; LIGHT;
D O I
10.1002/anie.201906692
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The potential of merging photoredox and nickel catalysis to perform multicomponent alkene difunctionalizations under visible-light irradiation is demonstrated here. Secondary and tertiary alkyl groups, as well as sulfonyl moieties can be added to the terminal position of the double bond with simultaneous arylation of the internal carbon atom in a single step under mild reaction conditions. The process, devoid of stoichiometric additives, benefits from the use of bench-stable and easy-to-handle reagents, is operationally simple, and tolerates a wide variety of functional groups.
引用
收藏
页码:12286 / 12290
页数:5
相关论文
共 89 条
[1]   Direct Synthesis of Secondary Benzylic Alcohols Enabled by Photoredox/Ni Dual-Catalyzed Cross-Coupling [J].
Alam, Rauful ;
Molander, Gary A. .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24) :13728-13734
[2]  
[Anonymous], 2016, ANGEW CHEM
[3]   Sulfinate derivatives: dual and versatile partners in organic synthesis [J].
Aziz, Jessy ;
Messaoudi, Samir ;
Alami, Mouad ;
Hamze, Abdallah .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (48) :9743-9759
[4]   Engaging sulfinate salts via Ni/photoredox dual catalysis enables facile Csp2-SO2R coupling [J].
Cabrera-Afonso, Maria Jesus ;
Lu, Zhi-Peng ;
Kelly, Christopher B. ;
Lang, Simon B. ;
Dykstra, Ryan ;
Gutierrez, Osvaldo ;
Molander, Gary A. .
CHEMICAL SCIENCE, 2018, 9 (12) :3186-3191
[5]   One pot and selective intermolecular aryl- and heteroaryl-trifluoromethylation of alkenes by photoredox catalysis [J].
Carboni, Aude ;
Dagousset, Guillaume ;
Magnier, Emmanuel ;
Masson, Geraldine .
CHEMICAL COMMUNICATIONS, 2014, 50 (91) :14197-14200
[6]   Visible light photoredox-controlled reactions of N-radicals and radical ions [J].
Chen, Jia-Rong ;
Hu, Xiao-Qiang ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2044-2056
[7]   Transition Metal-Free 1,2-Carboboration of Unactivated Alkenes [J].
Cheng, Ying ;
Mueck-Lichtenfeld, Christian ;
Studer, Armido .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (20) :6221-6225
[8]   One-Pot Synthesis of Allylic Sulfones, Ketosulfones, and Triflyl Allylic Alcohols from Domino Reactions of Allylic Alcohols with Sulfinic Acid under Metal-Free Conditions [J].
Chu, Xue-Qiang ;
Meng, Hua ;
Xu, Xiao-Ping ;
Ji, Shun-Jun .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (32) :11359-11368
[9]  
Corce V., 2015, Angewandte Chemie, V127, P11576, DOI DOI 10.1021/ol5021477
[10]   Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds [J].
Corce, Vincent ;
Chamoreau, Lise-Marie ;
Derat, Etienne ;
Goddard, Jean-Philippe ;
Ollivier, Cyril ;
Fensterbank, Louis .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (39) :11414-11418