- Graphene oxide-catalyzed synthesis of benzothiazoles with amines and elemental sulfur via oxidative coupling strategy of amines to imines
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The graphene oxide-catalyzed coupling and cyclization reactions of primary amines with elemental sulfur was developed to afford various optically property benzothiazoles. This coupling and cyclization strategies proceeded under the oxidant system graphene oxide/O2 and constructed carbon-heteroatom (N, S) bonds with amines and elemental sulfur. Due to benzothiazoles as common chromophores, these products exhibited intriguing fluorescence properties, including outstanding Stokes shifts (up to 161 nm) and quantum yields (up to 74%). Utilizing the products’ unique fluorescence response in different solvents, β-naphthothiazole 4a showed excellent aggregation-induced emission properties in 1,2-dichloroethane, which was 60 times higher than in tetrahydrofuran.
- He, Haiping,Duan, Dehao,Li, Hong,Wei, Yifei,Nie, Liang,Tang, Bo,Wang, Hanyu,Han, Xiaowei,Huang, Panpan,Peng, Xiangjun
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- Inkable CF3-functionalized benzothiazole/benzimidazole-Ir(III) complexes for efficient bilayer-inkjet-printed OLEDs
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The inkjet-printed organic light-emitting diodes (OLEDs) are gradually gaining popularity due to their low cost, free vacuum environment, patterning, and large-area display capability, but inkable phosphors are yet less reported. In order to develop inkab
- Chi, Hai-Jun,Dong, Yan,Hu, Yong-Xu,Li, Xiao,Li, Xing-Chen,Liao, Hao-Sen,Lv, Yan-Li,Xia, Xin,Xie, Dong-Dong,Zhang, Dong-Yu
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supporting information
(2021/11/19)
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- Photoinduced Heterogeneous C?H Arylation by a Reusable Hybrid Copper Catalyst
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Heterogeneous copper catalysis enabled photoinduced C?H arylations under exceedingly mild conditions at room temperature. The versatile hybrid copper catalyst provided step-economical access to arylated heteroarenes, terpenes and alkaloid natural products with various aryl halides. The hybrid copper catalyst could be reused without significant loss of catalytic efficacy. Detailed studies in terms of TEM, HRTEM and XPS analysis of the hybrid copper catalyst, among others, supported its outstanding stability and reusability.
- Choi, Isaac,Müller, Valentin,Lole, Gaurav,K?hler, Robert,Karius, Volker,Vi?l, Wolfgang,Jooss, Christian,Ackermann, Lutz
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supporting information
p. 3509 - 3514
(2020/03/03)
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- Benzothiazole Synthesis: Mechanistic Investigation of an in Situ-Generated Photosensitizing Disulfide
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The use of a visible light absorbing intermediate as a photosensitizer makes a chemical process simple and sustainable, obviating the need for the use of chemical additives. Herein, the formation of a photosensitizing disulfide in benzothiazole synthesis from 2-Aminothiophenol and aldehydes was proposed and confirmed through in-depth mechanistic studies. A series of photophysical and electrochemical investigations revealed that an in situ-generated disulfide photosensitizes molecular oxygen to generate the key oxidants, singlet oxygen and superoxide anion, for the dehydrogenation step.
- Hwang, Ho Seong,Lee, Sumin,Han, Sung Su,Moon, Yu Kyung,You, Youngmin,Cho, Eun Jin
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p. 11835 - 11843
(2020/10/23)
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- Cuprous cluster as effective single-molecule metallaphotocatalyst in white light-driven C[sbnd]H arylation
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This study investigated a series of ferrocenyltelluroether based cuprous halide clusters as effective single-molecule metallaphotocatalysts (SMP) in white light-driven C[sbnd]H arylation at room temperature and air. A systematic mechanistic study reveals that Cu(I) cluster can be irradiated by visible light to promote proton-coupled electron transfer (PCET), during which the electron from Cu(I)* leaves together with the proton from benzothiazole C[sbnd]H, leading to the formation of benzothiazolate-coordinated Cu(II) intermediate and aryl radical. Subsequently, the electron transfer (ET) from the ferrocene unit to the Cu(II) center releases the reactive benzothiazolate to form the target product with aryl radical. The advantages of these copper(I) halide clusters as SMP include high photocatalytic efficiency, structure adjustability, mild reaction conditions and good functional group tolerance.
- Ji, Wei,Wang, Hao,Li, Cheng-An,Gao, Fei,An, Zhong-Fu,Huang, Ling,Wang, He,Pan, Yue,Zhu, Dun-Ru,Wang, Jian-Qiang,Guo, Cheng,Mayoral, José A.,Jing, Su
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p. 270 - 276
(2019/09/30)
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- Synthesis of 2-substituted benzothiazoles via the Br?nsted acid catalyzed cyclization of 2-amino thiophenols with nitriles
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A convenient and efficient method for the synthesis of 2-substituted benzothiazoles from simple and readily available 2-amino thiophenols and nitriles is described. The Br?nsted acid-catalyzed cyclization reaction was performed under metal and solvent-free conditions.
- Yu, Xiaoqiang,Yin, Qing,Zhang, Zhiheng,Huang, Tianyu,Pu, Zichao,Bao, Ming
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supporting information
p. 1964 - 1966
(2019/06/27)
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- Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands
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Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.
- Mishra, Nidhi,Singh, Anoop S.,Agrahari, Anand K.,Singh, Sumit K.,Singh, Mala,Tiwari, Vinod K.
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p. 389 - 399
(2019/05/06)
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- Elemental Sulfur-Mediated Decarboxylative Redox Cyclization Reaction: Copper-Catalyzed Synthesis of 2-Substituted Benzothiazoles
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A S 8 -mediated directed decarboxylative redox-cyclization strategy for the synthesis of 2-substituted benzothiazoles from o -iodoanilines, arylacetic acids, and elemental sulfur catalyzed by cheap copper metal has been developed. This reaction is operationally simple, ligand-free, compatible with a wide range of functional groups, and provides the desired products in good to excellent yields. In addition, a gram-scale experiment was carried out to furnish PMX 610, an antitumor drug.
- Wang, Xin,Li, Xiaotong,Hu, Renhe,Yang, Zhao,Gu, Ren,Ding, Sai,Li, Pengyi,Han, Shiqing
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supporting information
p. 219 - 224
(2017/10/09)
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- Nickel-Catalyzed Coupling of Azoles with Aromatic Nitriles
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This manuscript describes the Ni-catalyzed coupling of azoles with aromatic nitriles. The use of BPh3 promotes these arylations with electronically diverse azoles and benzonitriles. While the nickel catalyst is necessary for the arylations of phenyl oxazoles, arylation of benzoxazoles with some nitriles affords the arylated products even in the absence of the Ni catalyst albeit in lower yield than the catalyzed process. The Ni-catalyzed process exhibits higher rates and a broader scope than the uncatalyzed transformation.
- Hanson, McKenna G.,Olson, Noelle M.,Yi, Zubaoyi,Wilson, Grace,Kalyani, Dipannita
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supporting information
p. 4271 - 4274
(2017/08/23)
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- A 2 - aryl benzo thiazole synthetic method of compound
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The invention relates to the technical field of pharmaceutical chemical engineering intermediates and provides a synthesis method of a 2-arylbenzothiazole compound. The synthesis method comprises the following steps: (a) orderly adding an o-aminophenylthiophenol derivative, an aryl nitrile derivative and a protonic acid catalyst to a Schlenk bottle, putting the Schlenk bottle into oil bath for heating for reacting for 14 hours, and controlling the temperature within the range of 25-120 DEG C, wherein the molar ratio of the o-aminophenylthiophenol derivative to the aryl nitrile derivative is 1: 1, and the molar ratio of the o-aminophenylthiophenol derivative to the protonic acid catalyst is 1: (0.01-0.2); (b) after the reaction is ended, taking water and ethyl acetate as an extracting agent for extracting, and drying the organic phase after extracting by use of anhydrous Na2SO4, thereby obtaining a coarse target product benzothiazole; and (c) recrystallizing the coarse target product benzothiazole, and filtering by use of filter paper after white crystals are completely separated out, thereby obtaining the 2-arylbenzothiazole compound. The synthesis method is simple in steps, easily available in raw materials and mild in reaction conditions.
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Paragraph 0048; 0049; 0050
(2017/08/25)
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- Elemental sulfur mediated cyclization via redox strategy: Synthesis of benzothiazoles from o-chloronitrobenzenes and benzyl chlorides
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A novel metal-free synthesis of 2-substituted benzothiazoles from easily available o-chloronitrobenzenes and benzyl chlorides using elemental sulfur as traceless oxidizing agent has been developed. The protocol provides a simple, efficient, and atom-economic way to access to benzothiazoles in moderate to excellent yields. And the approach exhibited good functional group tolerance.
- Wang, Xin,Miao, Dazhuang,Li, Xiaotong,Hu, Renhe,Yang, Zhao,Gu, Ren,Han, Shiqing
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supporting information
p. 5194 - 5199
(2017/07/28)
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- Photoinduced Copper-Catalyzed C-H Arylation at Room Temperature
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Room-temperature azole C-H arylations were accomplished with inexpensive copper(I) compounds by means of photoinduced catalysis. The expedient copper catalysis set the stage for site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine. Copper light: Room-temperature C-H arylations of heteroarenes were accomplished with inexpensive copper compounds by photoinduced catalysis. The expedient copper catalysis leads to site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine.
- Yang, Fanzhi,Koeller, Julian,Ackermann, Lutz
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supporting information
p. 4759 - 4762
(2016/04/19)
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- Copper-catalyzed multicomponent reactions of 2-iodoanilines, benzylamines, and elemental sulfur toward 2-arylbenzothiazoles
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A relatively cheap copper salt-catalyzed, three-component approach providing 2-arylbenzothiazoles in good to excellent yields from readily available 2-iodoanilines, benzylamines, and sulfur powder is reported. This methodology allows preparation of various classes of 2-arylbenzothiazoles and provides a general, reliable approach.
- Wang, Rui,Ding, Yong-Liang,Liu, Hong,Peng, Shu,Ren, Jie,Li, Lei
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p. 945 - 949
(2015/02/19)
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- METHOD FOR PREPARING BENZOTHIAZOLE AND DERIVATIVES
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The present invention relates to a method for preparing benzothiazole and derivatives of the same and, more specifically, to a method for preparing benzothiazole derivatives using aminothiophenol derivatives, aldehyde, oxygen, and photocatalyst under the condition in which visible rays are radiated to react in a simple condition while synthesizing benzothiazole derivatives having various forms in high yield.COPYRIGHT KIPO 2015
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Paragraph 0223-0230
(2016/10/24)
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- Iron catalyzed oxidative assembly of N-heteroaryl and aryl metal reagents using oxygen as an oxidant
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An equivalent amount of N-heteroaryl and aryl Grignard or lithium reagents, after mediation by an equivalent of titanate, was facilely coupled to furnish N-heteroaryl-aryl compounds under the catalysis of FeCl3/TMEDA at ambient temperature using oxygen as an oxidant. Most of the common N-heteroaryls were all good candidates, and thus provided a general, green and pratical protocol for the flexible construction of various N-heteroaryl-aryl structures. This journal is
- Liu, Kun Ming,Liao, Lian Yan,Duan, Xin Fang
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supporting information
p. 1124 - 1127
(2015/01/09)
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- Copper-catalyzed multicomponent reactions of 2-iodoanilines, benzylamines, and elemental sulfur toward 2-arylbenzothiazoles
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A relatively cheap copper salt-catalyzed, three-component approach providing 2-arylbenzothiazoles in good to excellent yields from readily available 2-iodoanilines, benzylamines, and sulfur powder is reported. This methodology allows preparation of various classes of 2-arylbenzothiazoles and provides a general, reliable approach.
- Wang, Rui,Ding, Yong-Liang,Liu, Hong,Peng, Shu,Ren, Jie,Li, Lei
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p. 945 - 949
(2014/02/14)
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- Synthesis of 2-substituted benzothiazoles by visible light-driven photoredox catalysis
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An efficient method for synthesis of the widely applicable 2-substituted benzothiazoles has been developed. The process requires only 0.1 mol% [Ru(bpy)3Cl2], O2, and visible light irradiation with substrates: 2-aminothiophenol and a variety of aldehydes. We established an oxidative quenching of the photoredox catalyst as being the key process in this photoelectrocatalytic cycle. Copyright
- Yu, Chunghyeon,Lee, Kyungyub,You, Youngmin,Cho, Eun Jin
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supporting information
p. 1471 - 1476
(2013/06/27)
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- Efficient 2-aryl benzothiazole formation from aryl ketones and 2-aminobenzenethiols under metal-free conditions
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2-Aryl benzothiazole formation from aryl ketones and 2-aminobenzenethiols under metal- and I2-free conditions was described. Various 2-aryl benzothiazoles were selectively obtained in good yields using molecular oxygen as oxidant. DMSO played an important role in this transformation. Functional groups such as methyl, methoxy, fluoro, chloro, bromo and nitro groups were tolerated under the optimized reaction conditions.
- Liao, Yunfeng,Qi, Hongrui,Chen, Shanping,Jiang, Pengcheng,Zhou, Wang,Deng, Guo-Jun
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supporting information
p. 6004 - 6007
(2013/02/22)
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- Nickel-catalyzed C-H arylation of azoles with haloarenes: Scope, mechanism, and applications to the synthesis of bioactive molecules
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Novel nickel-based catalytic systems for the C-H arylation of azoles with haloarenes and aryl triflates have been developed. We have established that Ni(OAc)2/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)2/dppf (dppf=1,1′-bis(diphenylphosphino)ferrocene) system was found to be effective. Thiazoles, benzothiazoles, oxazoles, benzoxazoles, and benzimidazoles can be used as the heteroarene coupling partner. Upon further investigation, we discovered a new protocol for the present coupling using Mg(OtBu)2 as a milder and less expensive alternative to LiOtBu. Attempts to reveal the mechanism of this nickel-catalyzed heterobiaryl coupling are also described. This newly developed methodology has been successfully applied to the syntheses of febuxostat (a xanthine oxidase inhibitor that is effective for the treatment of gout and hyperuricemia), tafamidis (effective for the treatment of TTR amyloid polyneuropathy), and texaline (a natural product having antitubercular activity). Copyright
- Yamamoto, Takuya,Muto, Kei,Komiyama, Masato,Canivet, Jerome,Yamaguchi, Junichiro,Itami, Kenichiro
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supporting information; experimental part
p. 10113 - 10122
(2011/10/08)
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- A palladium/copper bimetallic catalytic system: Dramatic improvement for Suzuki-Miyaura-type direct C-H arylation of azoles with arylboronic acids
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Bimetallic catalytic system: Palladium/copper bimetallic-catalyzed Suzuki-Miyaura-type coupling has been disclosed for direct C-H arylation of azoles, instead of azole halides or pseudohalides, with arylboronic acids (see scheme).
- Liu, Bo,Qin, Xurong,Li, Kaizhi,Li, Xiyu,Guo, Qiang,Lan, Jingbo,You, Jingsong
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supporting information; experimental part
p. 11836 - 11839
(2011/01/12)
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- Palladium(0) nanoparticles-catalyzed ligand-free direct arylation of benzothiazole via C-H bond functionalization
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Palladium nanoparticles, generated in situ efficiently catalyzes direct 2-C-H arylation of benzothiazole without requirement of any ligand. A wide range of substituted aryl and heteroaryl iodides participate in this reaction producing a series of 2-aryl/heteroaryl-benzothiazoles in high yields.
- Saha, Debasree,Adak, Laksmikanta,Ranu, Brindaban C.
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experimental part
p. 5624 - 5627
(2010/11/03)
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- Nickel-catalyzed biaryl coupling of heteroarenes and aryl halides/triflates
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Ni-based catalytic systems for the arylation of heteroarenes with aryl halides and triflates have been established. Ni(OAc)2/bipy is a general catalyst for aryl bromides/iodides, and Ni(OAc)2/dppf is effective for aryl chlorides/triflates. Thiazole, benzothiazole, oxazole, benzoxazole, and benzimidazole are applicable as heteroarene coupling partners. A rapid synthesis of febuxostat, a drug for gout and hyperuricemia, is also demonstrated.
- Canivet, Jerome,Yamaguchi, Junichiro,Ban, Ikuya,Itami, Kenichiro
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supporting information; experimental part
p. 1733 - 1736
(2009/08/15)
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- A SYNTHESIS OF 2-SUBSTITUTED PHENYLBENZOTHIAZOLES
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A one-pot synthesis of 2-substituted phenylbenzothiazoles is achieved when 2-aminobenzenethiol is treated with an excess of sodium hydride and aromatic nitriles in THF.This method allows to obtain substituted products (F, CF3, Cl or OCH3) in each ortho, m
- Mettey, Yvette,Michaud, Sabine,Vierfond, Jean Michel
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p. 1001 - 1006
(2007/10/02)
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- 1-Methyl-2-pyrrolidinone: A Well-Adapted Solvent in the Benzothiazoles Synthesis
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We describe the synthesis of a series of 2-aryl and 2-alkyl benzothiazoles with high yields using 1-methyl-2-pyrrolidinone as reaction solvent.
- Brembilla, A.,Roizard, D.,Lochon, P.
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p. 3379 - 3384
(2007/10/02)
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