Palladium-Catalyzed Oxidative Carbonylation of Diarylamines for the Synthesis of Acridone Derivatives

被引:0
作者
Guo, Wenting [1 ]
Wu, Wenting [1 ]
Huang, Jiali [1 ]
Zhang, Chengyan [1 ]
Wang, Huiyan [1 ]
Zhou, Hualan [1 ]
Hu, Weiming [1 ]
机构
[1] Jiangsu Ocean Univ, Sch Environm & Chem Engn, Lianyungang 222005, Jiangsu, Peoples R China
关键词
Pd-catalyzed; Dual C-H activation; Carbonylation; Acridone derivatives; Safe CO source; MICROWAVE-ASSISTED SYNTHESIS; METAL-FREE SYNTHESIS; ONE-POT SYNTHESIS; C-BOND FORMATION; DIMETHYL-SULFOXIDE; MEDIATED SYNTHESIS; ARYL BROMIDES; H ACTIVATION; AMINOCARBONYLATION; ALCOHOLS;
D O I
10.1002/ajoc.202300584
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd-catalyzed oxidative dual C-H carbonylation has been developed starting from commercially available diarylamines, in which the Cr(CO)6 served as a safe carbonyl source. This method provides a facile and atom-economic approach toward diversified acridone derivatives in moderate to good yields, which features with good functional group compatibility, operational safety and easy scale-up. A Pd-catalyzed oxidative dual C-H carbonylation has been developed starting from commercially available diarylamines, in which the Cr(CO)6 served as a safe carbonyl source. This method provides a facile and atom-economic approach toward diversified acridone derivatives in moderate to good yields, which features with good functional group compatibility, operational safety and easy scale-up.image
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页数:5
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共 118 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]   Palladium-Catalyzed Molybdenum Hexacarbonyl-Mediated Gas-Free Carbonylative Reactions [J].
Akerbladh, Linda ;
Odell, Luke R. ;
Larhed, Mats .
SYNLETT, 2019, 30 (02) :141-155
[3]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[4]   Microwave-assisted, Mo(CO)6-mediated, palladium-catalyzed amino-carbonylation of aryl halides using allylamine:: from exploration to scale-up [J].
Appukkuttan, Prasad ;
Axelsson, Linda ;
Van der Eycken, Erik ;
Larhed, Mats .
TETRAHEDRON LETTERS, 2008, 49 (39) :5625-5628
[5]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
[6]   Intermolecular Pauson-Khand-Type Reaction of Vinyl Iodides with Alkynes and a CO Surrogate [J].
Boehm, Philip ;
Denton, Elliott H. ;
Wick, Joel ;
Morandi, Bill .
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (08) :5069-5077
[7]   Chiral N,NLigands Enabling Palladium-Catalyzed Enantioselective Intramolecular Heck-Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions [J].
Carmona, Rafaela C. ;
Koster, Otto D. ;
Duarte Correia, Carlos Roque .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (37) :12067-12070
[8]   A Palladium-Catalyzed Domino Procedure for the Synthesis of Unsymmetrical Ureas [J].
Chen, Bo ;
Peng, Jin-Bao ;
Ying, Jun ;
Qi, Xinxin ;
Wu, Xiao-Feng .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (15) :2820-2824
[9]   Atroposelective carbonylation of aryl iodides with amides: facile synthesis of enantioenriched cyclic and acyclic amides [J].
Chen, Li-Ping ;
Chen, Jiang-Fei ;
Zhang, Yu-Jiao ;
He, Xing-Yi ;
Han, Ya-Fei ;
Xiao, Yu-Ting ;
Lv, Gui-Fen ;
Lu, Xin ;
Teng, Fan ;
Sun, Qing ;
Li, Jin-Heng .
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (21) :6067-6073
[10]   Palladium-Catalyzed Enantioselective Heck Carbonylation with a Monodentate Phosphoramidite Ligand: Asymmetric Synthesis of (+)-Physostigmine, (+)-Physovenine, and (+)-Folicanthine [J].
Chen, Ming ;
Wang, Xucai ;
Yang, Pengfei ;
Kou, Xun ;
Ren, Zhi-Hui ;
Guan, Zheng-Hui .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (29) :12199-12205