- Synthesis of 1,2,3-Fused Indole Polyheterocycles by Copper-Catalyzed Cascade Reaction
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A one-pot reaction has been devloped for the preparation of 1,2,3-fused indole polyheterocycles by starting from 2-iodobenzamide and 2-iodobenzyl cyanide in the presence of a copper catalyst. The cascade process involves the efficient formation of one C–C
- Kavala, Veerababurao,Yang, Zonghan,Konala, Ashok,Yang, Tang-Hao,Kuo, Chun-Wei,Ruan, Jian-Yao,Yao, Ching-Fa
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- Palladium-Catalyzed Dearomative Arylvinylation Reaction of Indoles with N-Arylsulfonylhydrazones
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A Pd-catalyzed dearomative arylvinylation reaction of indoles with N-arylsulfonylhydrazones as coupling partners is developed, which proceeds via a domino sequence involving dearomative carbopalladation, Pd-carbene migratory insertion, and regioselective
- Liang, Ren-Xiao,Wang, Ke,Wu, Quan,Sheng, Wei-Jian,Jia, Yi-Xia
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- α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles
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A novel palladium-catalyzed decarboxylative cascade cyclization for the assembly of diverse fused heteropolycycles by employing α-oxocarboxylic acids as three-carbon insertion units is reported. This protocol enables the synthesis of isoquinolinedione- and indolo[2,1-a]isoquinolinone-fused benzocycloheptanones in moderate to good yields by the use of different aryl iodides, including alkene-tethered 2-iodobenzamides and 2-(2-iodophenyl)-1H-indoles. Notably, the approach achieves simultaneous construction of both six- and seven-membered rings via sequential intramolecular carbopalladation, C-H activation, and decarboxylation.
- Zhou, Liwei,Qiao, Shujia,Zhou, Fengru,Xuchen, Xinyu,Deng, Guobo,Yang, Yuan,Liang, Yun
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supporting information
p. 2878 - 2883
(2021/05/05)
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- Palladium-Catalyzed Asymmetric Intramolecular Dearomative Heck Annulation of Aryl Halides to Furnish Indolines
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An unprecedented Pd-catalyzed asymmetric intramolecular cascade cyclization of aryl halides with readily available arylboronic acids proceeds through a Heck-type dearomative cyclization terminated with arylation in the presence of Pd2(dba)3 (10 mol %), Cu
- Li, Yuanfeng,Zhang, Hong-Yu,Zhang, Yuecheng,Han, Ya-Ping,Zhao, Jiquan,Liang, Yong-Min
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p. 14640 - 14651
(2021/11/01)
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- Palladium-Catalyzed Amination/Dearomatization Reaction of Indoles and Benzofurans
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This report describes a palladium-catalyzed dearomatization and amination tandem reaction of 2,3-disubstituted indoles and benzofurans via the Catellani strategy. This reaction provides a new method for the construction of amino-substituted indoline-fused cyclic and benzofuran spiro compounds in good yields. The reaction has broad functional group compatibility and substrate scope.
- Zhang, Zhe,Zhang, Bo-Sheng,Li, Kai-Li,An, Yang,Liu, Ce,Gou, Xue-Ya,Liang, Yong-Min
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p. 7817 - 7839
(2020/07/16)
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- Palladium-Catalyzed Domino Heck/C-H Activation/Decarboxylation: A Rapid Entry to Fused Isoquinolinediones and Isoquinolinones
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A new palladium-catalyzed tandem cyclization of various alkene-tethered aryl iodides has been presented. In this protocol, o-bromobenzoic acids are employed as coupling parters to achieve the insertion of aromatic rings by the cleavage of C(sp2)-Br and decarboxylation, thus assembling various dibenzoisoquinolinediones and dibenzoisoquinolinones. In addition, a seven-membered ring can be constructed by the use of 8-bromo-1-naphthoic acid. Notably, this approach enables regioselective product formation and features broad substrate scope.
- Luo, Xiai,Zhou, Liwei,Lu, Haiyan,Deng, Guobo,Liang, Yun,Yang, Chunming,Yang, Yuan
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supporting information
p. 9960 - 9964
(2019/12/24)
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- Palladium-Catalyzed Domino Allenamide Carbopalladation/Direct C-H Allylation of Heteroarenes: Synthesis of Primprinine and Papaverine Analogues
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Palladium-catalyzed intramolecular carbopalladation onto allenamides completed by direct C-H allylation of heterocycles is studied. The domino construction/heteroarylation of isoquinolone process is first achieved. A general three-step one-pot strategy, i
- Hédouin, Jonathan,Schneider, Cédric,Gillaizeau, Isabelle,Hoarau, Christophe
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supporting information
p. 6027 - 6032
(2018/10/05)
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- Copper-Catalyzed C(sp3)-S Bond and C(sp2)-S Bond Cross-Coupling of 2-(2-Iodobenzoyl) Substituted or 2-(2-Iodobenzyl) Substituted 1,2,3,4-Tetrahydroisoquinolines with Potassium Sulfide: Synthesis of Isoquinoline-Fused 1,3-Benzothiazine Scaffolds
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The sulfuration reaction of 2-(2-iodobenzoyl) substituted, or 2-(2-iodobenzyl) substituted 1,2,3,4-tetrahydroisoquinolines with potassium sulfide proceeded in the presence of copper catalysts to give tetrahydroisoquinoline-fused 1,3-benzothiazine scaffolds in moderate to appropriate yields. This protocol provided an efficient and simple strategy to construct the corresponding benzothiazine derivatives via formation of C(sp3)-S bond and C(sp2)-S bond, which the C-S bonds formed via different routes in this reaction (traditional cross-coupling reaction via the cleavage of C-I bond and oxidative cross-coupling reaction via C(sp3)-H bond functionalization).
- Dang, Pan,Zheng, Zhilei,Liang, Yun
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p. 2263 - 2268
(2017/02/26)
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- Palladium-Catalyzed Alkylation with Alkyl Halides by C(sp3)?H Activation
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Utilizing halogens as traceless directing goups represents an attractive strategy for C?H functionalization. A two C?H alkylation system, initiated by the oxidative addition of organohalides to Pd0, has been developed. The first reaction involves an intermolecular alkylation of palladacycles to form C(sp3)?C(sp2) bonds followed by C(sp2)?H activation/cyclization to deliver alkylated benzocyclobutenes as the final products. In the second reaction, two C?C bonds are formed by the reaction of palladacycles with CH2Br2, and provides a facile and efficient method for the synthesis of indanes. The alkylated benzocyclobutene products can be transformed into tricyclic hyrocarbons, and the indane derivatives are essential structural motifs in bioactive and odorant molecules.
- Wu, Zhuo,Ma, Ding,Zhou, Bo,Ji, Xiaoming,Ma, Xiaotian,Wang, Xiaoling,Zhang, Yanghui
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supporting information
p. 12288 - 12291
(2017/09/06)
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- Magnetically recyclable copper modified GO/Fe3O4 catalyst for efficient synthesis of quinazolinones
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A series of bioactive quinazolinones were effectively synthesized by the condensation of halide benzamide with amino acid using magnetically recyclable GO/Fe3O4-CuI as catalyst. Magnetic GO/Fe3O4-CuI was prepared via a simple chemical method and characterized by FTIR, powder XRD, and SEM. This heterogeneous copper catalyst can be easily separated from reaction mixtures by an external permanent magnet and reused without any obvious loss in activity which shows its applicability as a reusable and promising catalyst for quinazolinones synthesis.
- Kong, Lu-Lu,Fan, Li-Yan
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supporting information
p. 827 - 831
(2016/06/14)
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- Palladium-Catalyzed Carbonylative Annulation Reactions Using Aryl Formate as a CO Source: Synthesis of 2-Substituted Indene-1,3(2H)-dione Derivatives
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An efficient synthesis of 2-substituted indene-1,3(2H)-diones from stable and readily available 1-(2-halophenyl)-1,3-diones by employing phenyl formate as a CO source has been developed. The reaction occurred via palladium-catalyzed intramolecular carbonylative annulation using K3PO4 as a base and DMSO as a solvent at 95 °C. In this protocol, the reaction showed a broad substrate scope with good to excellent yields.
- Zhang, Ying,Chen, Jing-Lei,Chen, Zhen-Bang,Zhu, Yong-Ming,Ji, Shun-Jun
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p. 10643 - 10650
(2015/11/18)
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- Copper-catalyzed cross-coupling interrupted by an opportunistic smiles rearrangement: An efficient domino approach to dibenzoxazepinones
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Unexpected Smiles! An unusual and highly regioselective synthesis of dibenzoxazepinones by a domino sequence assisted by an unexpected Smiles rearrangement is reported. The process is effective on electronically differentiated phenols and shows a high tolerance to variation in the benzamide substituents. A plausible path for the reaction, supported by preliminary mechanistic data, is offered. Copyright
- Kitching, Matthew O.,Hurst, Timothy E.,Snieckus, Victor
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supporting information; experimental part
p. 2925 - 2929
(2012/05/04)
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