Article
Chemistry, Applied
Hongmei Zhu, Lei Chen, Rongxian Bai, Yanlong Gu
Summary: Two classes of indole-tetrahydropyridine hybrid molecules were synthesized via three-component reactions, providing a straightforward approach for accessing diverse molecular structures. The reactions were likely triggered by Michael addition, leading to the formation of indol-3-ylimine intermediate, which was then trapped by the indole component. The resulting indol-3-yl-substituted tetrahydropyridines could be converted into indole-pyridine hybrid molecules with the aid of DDQ.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Xianjie Yin, Helin Wang, Lei Shen, Qingle Zeng
Summary: A copper chloride-catalyzed three-component reaction of olefins, indoles, and diaryl diselenides under irradiation of blue LED light is presented. Various diaryl diselenides, including diheteroaryl diselenides, are suitable for this bifunctionalization of olefins. The reaction provides 26 examples of β-(hetero)arylselenyl indoles in 60%-87% yields, and the proposed mechanism involves the activation of diaryl diselenides, electrophilic addition of arylselenium cations to styrenes, and Friedel-Crafts-type alkylation at the 3-position of NH-indoles.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wei Wu, Beibei Luo, Yi You, Zhiqiang Weng
Summary: A novel synthesis approach for the construction of 2-trifluoroethyl-substituted benzofurans under copper-catalyzed conditions has been developed, with moderate to excellent yields (up to 93%). This method is also applicable to the formation of 2-trifluoroethylated indoles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Lu Lei, Pei-Sen Zou, Zhi-Xin Wang, Cui Liang, Cheng Hou, Dong-Liang Mo
Summary: A regioselective Heck reaction catalyzed by a P-containing palladacycle was described, which affords 2-aryl-2,5-dihydrofurans and 2-aryl-2,3-dihydrofurans in good yields from 2,3-dihydrofuran with diaryliodonium salts and aryl iodides, respectively. Mechanistic studies and DFT calculations revealed the chemoselectivity and regioselectivity-determining step of this reaction.
Article
Chemistry, Organic
Chao Xu, Ze He, Hongqin Yang, Hongyi Chen, Qingle Zeng
Summary: This study reports a FeCl3-catalyzed three-component arylation of alkenes with good to excellent yields. The method allows for the synthesis of complex products in a single step, with simple operation and commercially available reagents. A reasonable mechanism for the FeCl3-catalyzed arylation is proposed in the study.
Article
Chemistry, Organic
Jia Seo, Che-Wei Chen, Woohyeong Lee, Ju Eun Jeon, Pei-Ling Chen, Shih-Ching Chuang, Jung Min Joo
Summary: A benzannulation strategy was developed involving activation of two C-H bonds of five-membered heteroarenes, resulting in fluorescent benzofuran and indole derivatives through Pd-catalyzed oxidative reactions. This strategy provides a potential pathway for further development of functionalized polycyclic heteroaromatic compounds.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Yi-Ming Zhao, Xu Wang, Zi-Yi Guo, Hang Li, Ji-Tan Zhang, Mei-Hua Xie
Summary: A copper-catalyzed three-component reaction has been established for the synthesis of (Z)-1,2-bis(arylthio)alkenes via a syn-addition process involving ynones, aryl iodides, and elemental sulfur. The reaction shows practicality in operation, broad substrate scope, and the possibility of readily accessible scale-up synthesis with good to excellent yields. Additionally, benzo[b][1,4]dithiines can be efficiently constructed using 1,2-diiodobenzene as the coupling partner.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shubham Dutta, Akhila K. K. Sahoo
Summary: This paper describes a Pd-catalyzed three-component syn-1,2-arylmethylation method, which successfully synthesizes methyl-containing tetra-substituted olefins by using readily available and stable coupling partners iodo-arenes and methyl boronic acid. The reaction shows a broad scope with excellent functional-group tolerance and exhibits remarkable regio- and stereoselectivity. Biologically relevant motifs (BRM) bearing iodo-arenes and ynamides are also used for late-stage syn-1,2-arylmethylation of alkynes. Additionally, aryl-alkylation, aryl-trideuteriomethylation, alkynyl-methylation, and alkenyl-methylation of ynamides are presented, leading to the synthesis of synthetically important beta-amino-indenones and alpha-fluoro-alpha '-methyl ketones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Sudarshan Debnath, Lingli Liang, Mei Lu, Yian Shi
Summary: This study describes an efficient palladium-catalyzed multiple-C-N bond formation reaction for the synthesis of highly pi-conjugated N-heterocycles, indolo[3,2-b]indoles. The reaction likely proceeds through the initial formation of an indole-fused palladacycle by nucleophilic aminopalladation and subsequent bisamination to give indolo[3,2-b]indoles.
Article
Chemistry, Organic
Peng Wang, Ji Yang, Kangkang Sun, Helfried Neumann, Matthias Beller
Summary: The direct palladium-catalyzed selective carbonylative coupling of less reactive aryl chlorides with primary and secondary amines is achieved using a palladium/Xantphos catalyst system and cesium chloride as an additive. This reaction shows high conversion for various aryl chlorides and good functional group compatibility.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Jianxiao Li, Chenjing Hong, Yanan Niu, Bowen Wang, Wenfang Xiong, Huanfeng Jiang
Summary: A novel and reliable palladium-catalyzed oxylallylation reaction was developed for the synthesis of gem-difluorinated isoxazole derivatives. This strategy enables the direct combination of isoxazole motifs and gem-difluoroalkene units, which is challenging to achieve through conventional synthetic methods. The reaction proceeded with high atom- and step-economy and excellent functional group compatibility, providing structurally diverse products in moderate to good yields.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Inorganic & Nuclear
Qiang Li, Maoshuai Zhu, Xufei Yan, Ying Xia, Xiangge Zhou
Summary: A palladium-catalyzed annulative reaction between aniline and propargyl alcohol has been developed, resulting in versatile indole skeletons with potential applications. The reaction utilizes propargyl alcohols as internal or terminal alkynes for the formation of 3-alkenylindoles or 3-alkynylindoles through C-H/C-C activation.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Zhan-Yong Wang, Zhantong Liu, Aili Sun, Kai-Kai Wang
Summary: This review summarizes the recent advances in the three-component reactions of indoles between 2011-2021, including the classification and trigger mechanisms of the reactions, as well as their reactions with alkenes, alkynes, aldehydes, etc. The review also provides specific analysis to highlight the mechanisms involved, which will serve as references for future research in the field of indoles.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Adesh Kumar Singh, Rapelly Venkatesh, Vimlesh Kumar Kanaujiya, Varsha Tiwari, Jeyakumar Kandasamy
Summary: An efficient method for the synthesis of C-1 aryl enones from aryl iodides and glycal enones through palladium-catalyzed cross-coupling reactions under ligand-free conditions was developed. This method is applicable to a wide range of aryl iodides with different electron-donating and withdrawing groups, and can be carried out under mild reaction conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jianjun Wang, Xiaofeng Sun, Daguo Hu, Yian Shi
Summary: This work presents an efficient Pd-catalyzed method for synthesizing indoles, which involves the reaction of readily available vinyl bromides to produce a wide variety of indoles in high yields. The reaction likely proceeds through a sequential aryl C-H activation and bisamination process involving a resulting pallada(II)cycle with diaziridinone.
