Reductive Electrophotocatalytic α-C-H Arylation of Cyclic Ketones with Aryl Chlorides

被引:2
作者
Aman, Hasil [1 ]
Chang, Rui [1 ]
Ye, Juntao [1 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
electrophotocatalysis; arylation; aryl chlorides; cyclic ketones; electroreduction; CATALYZED DIRECT ARYLATION; ELECTRON-TRANSFER; 2-PHOTON EXCITATION; LIGHT; HALIDES; CYCLOPENTANONES; POTENTIALS; ACTIVATION; OXIDATION; EFFICIENT;
D O I
10.1002/cctc.202400635
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
alpha-Aryl cyclocarbonyls are important building blocks in organic synthesis. While many methods have been developed for their synthesis, the use of readily available and inexpensive aryl chlorides as the arylating reagent remains rare. Herein, we report an alpha-arylation of cyclic ketones with aryl chlorides under reductive electrophotocatalytic conditions. 2,6-Diisopropylphenyl-containing naphthalenemonoimide was identified as the optimal electrophotocatalyst, allowing for use of electron-deficient as well as electron-rich aryl chlorides under mild conditions. A transition metal-free approach for alpha-arylation of cyclic ketones using readily available and inexpensive aryl chlorides as the arylating reagent is achieved under electrophotocatalysis. image
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页数:5
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共 128 条
[1]   The standard redox potential of the phenyl radical/anion couple [J].
Andrieux, CP ;
Pinson, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (48) :14801-14806
[2]   Modular photoredox system with extreme reduction potentials based on pyridine catalysis [J].
Bai, Lutao ;
Jiao, Lei .
CHEM, 2023, 9 (11) :3245-3267
[3]   Synthetic Photoelectrochemistry [J].
Barham, Joshua P. ;
Koenig, Burkhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (29) :11732-11747
[4]   Organocatalytic regio- and asymmetric C-selective SNAr reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3′-oxoindoles [J].
Bella, M ;
Kobbelgaard, S ;
Jorgensen, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3670-3671
[5]   Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].
Bellina, Fabio ;
Rossi, Renzo .
CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146
[6]   The Rational Design of Reducing Organophotoredox Catalysts Unlocks Proton-Coupled Electron-Transfer and Atom Transfer Radical Polymerization Mechanisms [J].
Bortolato, Tommaso ;
Simionato, Gianluca ;
Vayer, Marie ;
Rosso, Cristian ;
Paoloni, Lorenzo ;
Benetti, Edmondo M. ;
Sartorel, Andrea ;
Leboeuf, David ;
Dell'Amico, Luca .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (03) :1835-1846
[7]   Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry [J].
Buglioni, Laura ;
Raymenants, Fabian ;
Slattery, Aidan ;
Zondag, Stefan D. A. ;
Noel, Timothy .
CHEMICAL REVIEWS, 2022, 122 (02) :2752-2906
[8]   Photoelectrochemically driven iron-catalysed C(sp3)-H borylation of alkanes [J].
Cao, Yangmin ;
Huang, Cheng ;
Lu, Qingquan .
NATURE SYNTHESIS, 2024, 3 (04) :537-544
[9]   Photoelectrochemical cross-dehydrogenative coupling of benzothiazoles with strong aliphatic C-H bonds† [J].
Capaldo, Luca ;
Quadri, Lorenzo L. ;
Merli, Daniele ;
Ravelli, Davide .
CHEMICAL COMMUNICATIONS, 2021, 57 (36) :4424-4427
[10]  
Carlo G., 1973, J AM CHEM SOC, V103, P7140