- Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents
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The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de
- Liang, Hao,Zhu, Guoxun,Pu, Xiaoyun,Qiu, Liqin
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p. 9246 - 9250
(2021/12/06)
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- Metal-Free and syn-Selective Hydrohalogenation of Alkynes through a Pseudo-Intramolecular Process
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A new metal-free hydrohalogenation method for alkynes has been developed, which proceeds through a pseudo-intramolecular process. In this reaction, ethynylaniline serves as a substrate to quantitatively form an anilinium salt upon treatment with hydrochloric acid. The spatial proximity facilitates the efficient electrophilic addition of HCl to the ethynyl group in syn-mode, affording the corresponding chloroalkene without overaddition. This protocol was applied to HBr and HI, and the corresponding bromo- and iodoalkenes were obtained, respectively. The obtained chloroalkene was converted to tri-substituted alkenes possessing different aryl/alkynyl groups through Pd-catalyzed cross-coupling reactions.
- Asahara, Haruyasu,Mukaijo, Yusuke,Muragishi, Kengo,Iwai, Kento,Ito, Akitaka,Nishiwaki, Nagatoshi
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p. 5747 - 5755
(2021/10/20)
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- Copper(I)-Mediated Cascade Annulation via Dual C-H/C-H Activation: Access to Benzo[a]carbazolic AEEgens
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A Cu(I)-mediated cascade cyclization/annulation of unprotectedo-alkynylanilines with maleimides in one pot is developed. The protocol offers sequential formation of one C-N and two C-C bonds to deliver fused benzo[a]carbazoles having free NH skeletons. The annulated products display fluorescence emission in the range of 485-502 nm with a large Stokes shift and fluorescence lifetime of ~17 ns. The annulated3aadisplays AEE behavior in the ethanol/hexane system and possesses marigold-flower-like morphology at the aggregated state. Cell viability assays enumerate biocompatible AEEgens, while their high intracellular fluorescence depicts cell imaging applicability.
- Khandelia, Tamanna,Ghosh, Subhendu,Panigrahi, Pritishree,Shome, Rajib,Ghosh, Siddhartha Sankar,Patel, Bhisma K.
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p. 16948 - 16964
(2021/12/02)
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- Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides
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N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20–99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes—after fragmentation of the cyclobutane ring—leads to enyne-metathesis-like products.
- de Souza, Wanderson C.,Matsuo, Bianca T.,Matos, Priscilla M.,Correia, José Tiago M.,Santos, Marilia S.,K?nig, Burkhard,Paix?o, Marcio W.
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supporting information
p. 3722 - 3728
(2021/02/03)
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- Gold(I)-Catalyzed Reactions between N-(o-Alkynylphenyl)imines and Vinyldiazo Ketones to Form 3-(Furan-2-ylmethyl)-1 H-indoles via Postulated Azallyl Gold and Allylic Cation Intermediates
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This work describes gold-catalyzed additions of vinyldiazo ketones to N-(o-alkynylphenyl)imines to yield 3-(furan-2-ylmethyl)-1H-indoles involving skeletal rearrangement; these new catalytic reactions are applicable to a wide range of substrates. We postu
- Kulandai Raj, Antony Sekar,Narode, Akshay Subhash,Liu, Rai-Shung
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supporting information
p. 1378 - 1382
(2021/03/03)
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- Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes
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The copper(ii)-catalyzed (4+1) cyclizations and copper(i)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionaliz
- Liang, Hao,He, Xiaobo,Zhang, Yaqi,Chen, Bin,Ouyang, Jia-Sheng,Li, Yongsu,Pan, Bendu,Subba Reddy, Chitreddy V.,Chan, Wesley Ting Kwok,Qiu, Liqin
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p. 11429 - 11432
(2020/10/12)
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- A competitive and highly selective 7-, 6- And 5-annulation with 1,3-migration through C-H and N-H-alkyne coupling
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We demonstrated a highly competitive and selective C-C and N-C cross-coupled 7-, 6- and 5-annulation utilizing 2-ethynylanilides to afford functionalized 1H-benzo[b]azepin-2(5H)-ones, 2-quinolinones, and 3-acylindoles in high yield. ZnCl2 was f
- Ajarul, Sk,Kayet, Anirban,Pati, Tanmay K.,Maiti, Dilip K.
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supporting information
p. 474 - 477
(2020/01/13)
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- Palladium-Catalyzed Ligand-Free Double Cyclization Reactions for the Synthesis of 3-(1′-Indolyl)-phthalides
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Indole and phthalide are privileged heterocyclic scaffolds in numerous natural products and bioactive molecules. The synthesis and biological evaluation of the compounds combining these two scaffolds have rarely been reported. Herein, we repot the first palladium-catalyzed ligand-free double cyclization reactions that enable efficient synthesis of 3-(1′-indolyl)-phthalides (42 examples, up to 96% yield) under mild conditions. Notably, only 1.0 mol % of catalyst loading is used, suggesting high efficiency. Late-stage elaborations give highly functionalized analogues.
- Yuan, Shuo,Zhang, Dan-Qing,Zhang, Jing-Ya,Yu, Bin,Liu, Hong-Min
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supporting information
p. 814 - 817
(2020/02/04)
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- Syntheses of N-Alkyl 2-Arylindoles from Saturated Ketones and 2-Arylethynylanilines via Cu-Catalyzed Sequential Dehydrogenation/Aza-Michael Addition/Annulation Cascade
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We describe here a Cu-catalyzed and 4-OH-TEMPO-mediated sequential dehydrogenation/aza-Michael addition/annulation cascade reaction for the construction of N-alkyl 2-arylindoles from facilely available saturated ketones and 2-arylethynylanilines. This rea
- Chen, Linlin,Ling, Fei,Liu, Tao,Ma, Yan,Song, Dingguo,Xiao, Lian,Xu, Min,Yu, Mengyao,Zhong, Weihui
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p. 3224 - 3233
(2020/03/23)
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- One-Pot Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source
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An atom-economical method for synthesizing N-heterocyclic indoles from readily available o-alkynylphenyl isothiocyanates and propargylamine derivatives is reported. This method involves a copper-catalyzed cascade bicyclization process consisting of an int
- Xie, Jialin,Guo, Zhonglin,Huang, Yuanqiong,Qu, Yi,Song, Hongjian,Song, Haibin,Liu, Yuxiu,Wang, Qingmin
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supporting information
p. 490 - 495
(2019/01/04)
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- Facile Synthesis of π-Conjugated Quinazoline-Substituted Ethenes from 2-Ethynylanilines and Benzonitriles under Transition-Metal-Free Conditions
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A new transition-metal-free version for the synthesis of π-conjugated quinazoline-substituted ethene derivatives from readily available starting materials has been developed. Quinazoline-substituted ethenes were obtained in moderate to high yields with completely Z-selectivity, and the resulting quinazoline-substituted ethenes show typical aggregation-induced emission (AIE) properties.
- Wang, Xu,Li, Jiawei,Huang, Yubing,Zhu, Jiayi,Hu, Rongrong,Wu, Wanqing,Jiang, Huanfeng
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p. 10453 - 10464
(2018/09/06)
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- Palladium-Catalyzed Oxidative [2 + 2 + 1] Annulation of 1,7-Diynes with H2O: Entry to Furo[3,4- c]quinolin-4(5 H)-ones
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A novel cascade annulation of 1,7-diynes with water has been developed for the synthesis of furo[3,4-c]quinolin-4(5H)-one skeletons with high atom- and step-economy. The transformation was enabled by a palladium catalyst in the presence of copper salt as
- Ouyang, Xuan-Hui,Tan, Fang-Lin,Song, Ren-Jie,Deng, Wei,Li, Jin-Heng
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supporting information
p. 6765 - 6768
(2018/10/24)
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- Nickel Catalysis Enables Hetero [2+2+1] Cycloaddition between Yne-Isothiocyanates and Isonitriles with Low Catalyst Loading
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Nickel(II) can be used to catalyze the hetero [2+2+1] cycloaddition of 2-alkynylaryl isothiocyanates and isonitriles in 2-methyltetrahydrofuran (2-MeTHF) to give a wide array of thieno[2,3-b]indoles in excellent yields. The reaction is featured by employi
- Liu, Rui-Juan,Wang, Peng-Fei,Yuan, Wen-Kui,Wen, Li-Rong,Li, Ming
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supporting information
p. 1373 - 1378
(2017/04/18)
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- Copper-catalyzed trifluoromethylazidation and rearrangement of aniline-linked 1,7-enynes: Access to CF3-substituted azaspirocyclic dihydroquinolin-2-ones and furoindolines
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A set of reactions involving copper-catalyzed trifluoromethylazidation and then rearrangement of aniline-linked 1,7-enynes with the relatively poorly reactive Togni reagent I and TMSN3 was developed, and provided facile access to structurally d
- Yu, Liu-Zhu,Wei, Yin,Shi, Min
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supporting information
p. 8980 - 8983
(2017/08/15)
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- Visible-Light Induced and Oxygen-Promoted Oxidative Cyclization of Aromatic Enamines for the Synthesis of Quinolines Derivatives
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The dual transition metal-visible light photoredox catalysis for the synthesis of quinoline derivatives by using dioxygen as an oxygen source is developed. By using visible light, the direct oxidative cyclization of aromatic enamines with alkynes or alkenes can be achieved at mild conditions with an aid of copper or palladium catalysts, and a variety of multisubstituted quinoline derivatives could be obtained in good to moderate yields under mild reaction conditions.
- Xia, Xiao-Feng,Zhang, Guo-Wei,Wang, Dawei,Zhu, Su-Li
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p. 8455 - 8463
(2017/08/23)
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- Palladium-Catalyzed Construction of Tetracyclic Scaffolds via the 1,7-Enyne Carbocyclization/Iodophenol Dearomatization Cascade
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An efficient palladium-catalyzed dearomatizing [2+2+1] carbocyclization of 1,7-enynes with iodophenols has been developed. A type of tetracyclic scaffold was built in this reaction, exhibiting a broad substrate scope with moderate to excellent yields. More importantly, this method provides a potential strategy for the synthesis of tetracyclic skeleton natural products.
- Xia, Yu,Wang, Li-Jing,Wang, Jia,Chen, Si,Shen, Yi,Guo, Chun-Huan,Liang, Yong-Min
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p. 12386 - 12394
(2017/12/08)
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- Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinolines through Indium(III)-Promoted Halocyclizations of N-Propargylic Sulfonylhydrazones
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A novel method for the preparation of 5,6-dihydropyrazolo[5,1-a]isoquinoline via indium(III)-promoted halocyclizations of N-propargylic sulfonylhydrazones has been developed. The pyrazole and 3,4-dihydroisoquinoline moieties were synchronously formed via
- Li, Ren-Hao,Ding, Cheng-Ke,Jiang, Ya-Nan,Ding, Zong-Cang,An, Xiao-Ming,Tang, Hai-Tao,Jing, Qi-Wei,Zhan, Zhuang-Ping
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supporting information
p. 1666 - 1669
(2016/04/26)
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- Transition-Metal Controlled Diastereodivergent Radical Cyclization/Azidation Cascade of 1,7-Enynes
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A strategy for achieving diastereodivergent azidations of enynes has been developed, employing azide transfer from the M-N3 complex to alkyl radicals. Following this concept, the diastereoselectivity has been switched by modulating the transition metals and the ligands. The Mn(III)-mediated radical cyclization/azidation cascade of 1,7-enynes afforded trans-fused pyrrolo[3,4-c]quinolinones, whereas the Cu(II)/bipyridine system gave cis-products.
- Zhao, Yingying,Hu, Yancheng,Wang, Haolong,Li, Xincheng,Wan, Boshun
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p. 4412 - 4420
(2016/06/09)
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- Access to Indole Derivatives from Diaryliodonium Salts and 2-Alkynylanilines
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An efficient, environmentally friendly, and operationally simple procedure to 1,2-disubstituted indoles from 2-alkynylanilines and diaryliodonium salts has been developed. This reaction proceeds smoothly under metal-free conditions. The products obtained could be transferred into 3,3′-diindolylmethane with DMSO catalyzed by palladium. The isotopic label experiments indicated that the methylene group in 3,3′-diindolylmethane is derived from DMSO. The diverse indoles were obtained in up to 90% yield for 28 examples.
- Li, Pengfei,Weng, Yunxiang,Xu, Xianxiang,Cui, Xiuling
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p. 3994 - 4001
(2016/06/09)
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- Expedient Access to Unsymmetrical Diarylindolylmethanes through Palladium-Catalyzed Domino Electrophilic Cyclization-Extended Conjugate Addition Approach
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A palladium-catalyzed domino process to access unsymmetrical diarylindolylmethanes has been developed through the annulation of o-alkynylanilines followed by 1,6-conjugate addition with p-quinone methides (p-QMs) under relatively mild conditions. The broad substrate scope of this methodology was demonstrated through the use of a wide range of substituted o-alkynylanilines and p-quinone methides, and in most cases, the unsymmetrical diarylindolylmethanes could be prepared in moderate to excellent yields. Notably, this method does not require any amino group protection. Moreover, 100% atom economy makes this transformation attractive from a green chemistry perspective.
- Reddy, Virsinha,Vijaya Anand, Ramasamy
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supporting information
p. 3390 - 3393
(2015/07/28)
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- A robust, well-defined homogeneous silver(I) catalyst for mild intramolecular hydroamination of 2-ethynylanilines leading to indoles
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A highly efficient, chemically stable and well-defined homogeneous silver(I) catalyst is reported for the room temperature, intramolecular hydroamination of 2-alkynylanilines leading to indole derivatives. Copyright
- McNulty, James,Keskar, Kunal
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p. 1622 - 1629
(2014/03/21)
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- A Robust, Well-Defined Homogeneous Silver(I) Catalyst for Mild Intramolecular Hydroamination of 2-Ethynylanilines Leading to Indoles
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A highly efficient, chemically stable and well-defined homogeneous silver(I) catalyst is reported for the room temperature, intramolecular hydroamination of 2-alkynylanilines leading to indole derivatives.
- McNulty, James,Keskar, Kunal
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p. 1622 - 1629
(2015/10/05)
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- Palladium-catalyzed intermolecular aerobic oxidative cyclization of 2-ethynylanilines with isocyanides: Regioselective synthesis of 4-halo-2-aminoquinolines
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A robust and regioselective palladium-catalyzed intermolecular aerobic oxidative cyclization of 2-ethynylanilines with isocyanides to the synthesis of 4-halo-2-aminoquinolines is reported herein. The procedure constructs various 4-halo-2-aminoquinolines w
- Liu, Bifu,Gao, Hanling,Yu, Yue,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 10319 - 10328
(2013/11/06)
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- Nucleopalladation triggering the oxidative heck reaction: A general strategy to diverse β-indole ketones
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A simple and efficient palladium-catalyzed oxidative coupling between 2-alkynyl anilines and allylic alcohols is described by using cheap and green dioxygen as the oxidant. These cross-couplings have a large functional group tolerance and are of higher re
- Wang, Qian,Huang, Liangbin,Wu, Xia,Jiang, Huanfeng
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supporting information
p. 5940 - 5943
(2014/01/06)
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- p-Toluenesulfonic acid promoted annulation of 2-alkynylanilines with activated ketones: Efficient synthesis of 4-Alkyl-2, 3-disubstituted quinolines
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Reactions between readily available 2-alkynylanilines and activated ketones such as ss-keto esters promoted by p-toluenesulfonic acid afford 4-alkyl-2, 3-disubstituted quinolines in good to excellent yields. The generality of substituents at the other end of the triple bond of 2-alkynylanilines makes the method a valuable approach to diversified 4-alkylquinolines, which are difficult to obtain by classical methods such as the Friedlaender reaction. Quinoline dimers can be prepared efficiently with alkyl or aryl linkers at C-4.
- Peng, Changlan,Wang, Yong,Liu, Lanying,Wang, Honggen,Zhao, Jiaji,Zhu, Qiang
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supporting information; experimental part
p. 818 - 822
(2010/04/02)
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- Multicomponent cascade reactions: A novel and expedient approach to functionalized indoles by an unprecedented nucleophilic addition- heterocyclization-oxidative alkoxycarbonylation sequence
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A novel multicomponent cascade process is reported, based on the sequential combination between an initial nucleophilic attack step to an imine moiety and a palladium-catalyzed oxidative heterocyclization-alkoxycarbonylation process. By this new process, five simple molecules [2-alkynylaniline imines, alcohol (ROH), carbon monoxide (CO), alcohol (ROH), and oxygen (O2)] are sequentially activated, selectively leading to high value-added functionalized indole derivatives in a single operation. Copyright
- Gabriele, Bartolo,Veltri, Lucia,Salerno, Giuseppe,Mancuso, Raffaella,Costa, Mirco
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supporting information; experimental part
p. 3355 - 3363
(2011/03/17)
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- One-pot/four-step/palladium-catalyzed synthesis of indole derivatives: The combination of heterogeneous and homogeneous systems
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One-pot, four-step syntheses of indoles using both solid-supported heterogeneous and homogeneous palladium catalysts and reagents were carried out. Such a combination of these two-phase catalysts and reagents causes a dramatic increase in yield, and it is a simple process. The presented methodology is effective for four-step reactions to provide various functionalized indoles.
- Sakai, Hayato,Tsutsumi, Ken,Morimoto, Tsumoru,Kakiuchia, Kiyomi
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supporting information; experimental part
p. 2498 - 2502
(2009/08/14)
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- Cinnolines and Pyrazolopyridazines. - Novel Synthetic and Mechanistic Aspects of the Richter Reaction
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The thermal cyclization of 2-alkynylbenzenediazonium salts 2 known as the Richter reaction and leading, as described in the literature, only to 4-hydroxycinnolines 6 has been studied.A new probable route to these compounds involving intermediate formation
- Vasilevsky, Sergei F.,Tretyakov, Eugene V.
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p. 775 - 780
(2007/10/02)
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