- Solid state fluorescent palladacycles with N-heterocyclic carbene-based ancillary ligands at room temperature
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Two pyrazine ligands 1-2 and their NHC-palladacycles 3-10 have been synthesized and fully characterized. Additionally, the detailed structures of 5-7 and 9 have been determined by X-ray diffraction and intermolecular π ? π and C-H ? X (Cl, N) interactions
- Xu, Chen,Wang, Zhi-Qiang,Yuan, Xiao-Er,Han, Xin,Xiao, Zhi-Qiang,Fu, Wei-Jun,Ji, Bao-Ming,Hao, Xin-Qi,Song, Mao-Ping
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Read Online
- Bis/hetero aromatic compound and preparation method thereof
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The invention discloses a bi/hetero aromatic compound and a preparation method thereof. The structural formula of the bi/hetero aromatic compound is as shown in formula 3. The preparation method comprises the following steps: taking an aryl tetrafluorobor
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Paragraph 0039-0040
(2021/07/17)
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- NaH-mediated direct C-H arylation in the presence of 1,10-phenanthroline
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Transition-metal-free coupling of haloarenes with unactivated arenes has been developed in the presence of NaH and 1,10-phenanthroline. Various haloarenes bearing methyl, methoxy, halogen (fluoride, chloride, and bromide), cyano, trifluoromethyl, ester, and amide groups can be cross-coupled with unactivated arenes, or heteroarenes in this reaction.
- Nozawa-Kumada, Kanako,Iwakawa, Yuki,Onuma, So,Shigeno, Masanori,Kondo, Yoshinori
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supporting information
p. 7773 - 7776
(2020/07/27)
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- Direct C-H photoarylation of diazines using aryldiazonium salts and visible-light
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In this study, direct C-H photoarylation of pyrazine with aryldiazonium salts under visible-light irradiation (blue-LEDs) is described, and additional examples including photoarylations of pyrimidine and pyridazine are also covered. The corresponding aryl-diazines were prepared in yields up to 84% only by mixing and irradiating the reaction with no need for an additional photocatalyst. We demonstrate the efficacy of this protocol by the scope with electron-donor, -neutral, and -withdrawing groups attached at the ortho, meta, and para positions of the aryldiazonium salts; the results are better than those reported for ruthenium-complex mediated photoarylations. Additionally, we demonstrate the robustness of this methodology with a 5 mmol scaled-up experiment. Mechanistic studies were carried out giving support to the proposal of a photocatalyzed approach by an electron donor-acceptor (EDA) complex, also highlighting the crucial role that solvents play in the formation of the EDA complex. This journal is
- Silva, Rodrigo C.,Villela, Lucas F.,Brocksom, Timothy J.,De Oliveira, Kleber T.
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p. 31115 - 31122
(2020/09/23)
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- Palladium-Catalyzed Electrophilic Functionalization of Pyridine Derivatives through Phosphonium Salts
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Herein, we report a highly efficient and practical method for pyridine-derived heterobiaryl synthesis through palladium-catalyzed electrophilic functionalization of easily available pyridine-derived quaternary phosphonium salts. The nice generality of this reaction was goes beyond arylation, enabling facile incorporation of diverse carbon-based fragments, including alkenyl, alkynyl, and also allyl fragments, onto the pyridine core. Notably, the silver salt additive is revealed to be of vital importance for the success of this transformation and its pivotal role as transmetallation mediator, which guarantees a smooth transfer of pyridyl group to palladium intermediate, is also described.
- Che, Yuan-Yuan,Deng, Xuezu,Feng, Chao,Lin, Ling-Zhi,Pei, Bingbing,Yue, Yanni
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supporting information
p. 16414 - 16419
(2020/07/20)
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- Electrochemical oxidation synergizing with Br?nsted-acid catalysis leads to [4 + 2] annulation for the synthesis of pyrazines
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An electrochemical dehydrogenative [4 + 2] annulation for the synthesis of pyrazines has been developed under undivided electrolytic conditions. In this protocol, neither external chemical oxidants nor transition-metal catalysts are needed, and a wide range of substituted pyrazines could be obtained from simple ketones and diamines in high efficiencies. Of note is that this electrolysis could also be extended for the construction of biheteroarenes and large π systems with good yields.
- Liu, Kun,Song, Chunlan,Wu, Jiarong,Deng, Yuqi,Tang, Shan,Lei, Aiwen
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supporting information
p. 765 - 769
(2019/02/27)
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- Urea-based organocatalyst catalyzed direct C–H bond arylations of unactivated arenes
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A simple 1,3-diethylurea was demonstrated to catalyze transition-metal-free arylations of unactivated aromatic C–H bonds with aryl iodides in the presence of t-BuOK. A broad range of aryl iodides with different arenes could couple in moderate to excellent yields. The mechanistic experiment results indicated that the radical is involved in this transformation.
- Zhao, Huaiqing,Xu, Xiangwen,Wu, Wei,Zhang, Wei,Zhang, Yunxian
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- Graphene oxide-phenalenyl composite: transition metal-free recyclable and catalytic C-H functionalization
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An efficient route towards a heterogeneous transition metal-free catalytic C-H functionalization using a covalently linked graphene oxide-phenalenyl conjugate is described herein (28 examples, which include a core of some biologically relevant biaryl and hetero-biaryls). It is an environmentally benign, economical and heterogeneous platform, whose catalytic activity can easily be regenerated through a simple washing-drying technique and the catalytic activity can be retained even after 10 cycles.
- Singh, Bhagat,Paira, Rupankar,Biswas, Goutam,Shaw, Bikash Kumar,Mandal, Swadhin K.
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supporting information
p. 13220 - 13223
(2018/12/10)
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- A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat-Water-Mediated Cross-Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents
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The Suzuki–Miyaura cross-coupling (SMC) reactions of several heteroaryl chlorides, benzyl chlorides, and aryl acid chlorides with (hetero)arylboron reagents have been investigated in the presence of [Pd(HL1)(PPh3)Cl2] (I) [HL1 = 3-[(2,6-diisopropylphenyl)-1-imidazolio]-2-quinoxalinide] as catalyst and K2CO3 as base in neat water. The synthesis of the heterocycle-containing biaryls required the addition of 2 mol-% of a phosphine ligand (PPh3 or X-Phos). A combination of more than 115 substrates were screened and it was found that I is a versatile catalyst that can produce heterocycle-containing biaryls, diarylmethanes, and benzophenones in moderate-to-excellent yields.
- Ramakrishna, Visannagari,Rani, Morla Jhansi,Reddy, Nareddula Dastagiri
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p. 7238 - 7255
(2018/01/01)
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- An active catalytic system for Suzuki-Miyaura cross-coupling reactions using low levels of palladium loading
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An easily available Pd(OAc)2/(2-(anthracen-9-yl)-1H-inden-3-yl) dicyclohexylphosphine/toluene/iPrOH/water catalytic system was developed, which shows high catalytic activity in the Suzuki-Miyaura cross-coupling reactions of a diverse array of aryl and heteroaryl chlorides with Pd loadings down to 0.01 mol%.
- Yan, Meng-Qi,Yuan, Jia,Lan, Fang,Zeng, Si-Hao,Gao, Meng-Yue,Liu, Sheng-Hua,Chen, Jian,Yu, Guang-Ao
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supporting information
p. 3924 - 3929
(2017/07/10)
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- Synthesis and Photophysical Properties of a Series of Pyrazine-Based Push–Pull Chromophores
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Eighteen push–pull pyrazine fluorophores are described. Methoxy, dimethylamino, and diphenylamino groups were used as electron-donating groups (EDGs), and six π-conjugated systems consisting of multiple bonds and 1,4-phenylene moieties were used to connec
- Hoffert, Kellyn,Durand, Rapha?l J.,Gauthier, Sébastien,Robin-le Guen, Fran?oise,Achelle, Sylvain
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p. 523 - 529
(2017/02/05)
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- Selective aryl radical transfers into N-heteroaromatics from diaryliodonoium salts with trimethoxybenzene auxiliary
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We have found that a series of trimethoxybenzene-based diaryliodonium(III) salts I (ArI+Ar’X-, where Ar = various aryl groups, Ar’ = 2,4,6-trimethoxyphenyl, X- = counterion) can exclusively cause Ar-transfers during the base-induced radical couplings with N-heteroaromatic compounds 1 by working the trimethoxybenzene ring (Ar’) as an inert coupling auxiliary. By the treatment with N-heteroaromatics 1 as the solvent, the metal-free arylations utilizing the specific salts I initiated by solid NaOH upon heating selectively produced the corresponding biaryls 2 in good yields without the formation of the trimethoxybenzene (Ar’) coupling product.
- Dohi, Toshifumi,Ueda, Shohei,Hirai, Akiko,Kojima, Yusuke,Morimoto, Koji,Kita, Yasuyuki
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p. 1272 - 1284
(2019/11/14)
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- Palladium-Catalyzed Decarbonylative Cross-Coupling of Azinecarboxylates with Arylboronic Acids
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The first palladium-catalyzed decarbonylative coupling of phenyl 2-azinecarboxylates and arylboronic acids is presented. The key for the development of this decarbonylative coupling is the use of Pd/dcype as a catalyst. A wide range of 2-azinecarboxylates can undergo the present coupling reaction to afford 2-arylazines. By combination with previously reported nickel-catalyzed decarbonylative coupling, we achieved a chemoselective sequential decarbonylative coupling of pyridine dicarboxylate to synthesize 2,4-diarylpyridine.
- Muto, Kei,Hatakeyama, Taito,Itami, Kenichiro,Yamaguchi, Junichiro
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supporting information
p. 5106 - 5109
(2016/10/14)
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- Efficient Iron-Catalyzed Kumada Cross-Coupling Reactions Utilizing Flow Technology under Low Catalyst Loadings
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An efficient continuous flow iron-catalyzed Kumada cross-coupling was developed for the coupling of 2-chloropyrazine and various aryl Grignard reagents in presence of low catalyst loadings (0.5 mol-%). Compared to batch mode, the continuous flow approach
- Buono, Frederic G.,Zhang, Yongda,Tan, Zhulin,Brusoe, Andrew,Yang, Bing-Shiou,Lorenz, Jon C.,Giovannini, Riccardo,Song, Jinhua J.,Yee, Nathan K.,Senanayake, Chris H.
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supporting information
p. 2599 - 2602
(2016/06/08)
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- Solid state fluorescent palladacycles with N-heterocyclic carbene-based ancillary ligands at room temperature
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Two pyrazine ligands 1-2 and their NHC-palladacycles 3-10 have been synthesized and fully characterized. Additionally, the detailed structures of 5-7 and 9 have been determined by X-ray diffraction and intermolecular ππ and C-HX (Cl, N) interactions were found in their crystal structures. These palladacycles are fluorescent in both the solid state and solution at room temperature.
- Xu, Chen,Wang, Zhi-Qiang,Fu, Wei-Jun,Ji, Bao-Ming,Yuan, Xiao-Er,Han, Xin,Xiao, Zhi-Qiang,Hao, Xin-Qi,Song, Mao-Ping
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supporting information
p. 1 - 5
(2015/09/02)
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- Photoinduced C-H direct arylation of unactivated arenes
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Two general protocols have been developed for the photoinduced, metal-free direct arylation of unactivated arenes with aryl iodide. Both methods gave good to excellent yields for most substrates. Notably, the C-F bond in method A and the C-F, C-Cl, and C-Br bonds in method B could survive the arylation reaction. These methods offered excellent options for syntheses of biaryls.
- Kan, Jian,Huang, Shijun,Zhao, Huaiqing,Lin, Jin,Su, Weiping
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p. 1329 - 1333
(2015/08/06)
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- Copper-catalyzed cross-coupling of aryl- and heteroaryltriethoxysilanes with aryl and heteroaryl iodides and bromides
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Copper(I)-catalyzed coupling of aryl- and heteroaryltriethoxysilanes with aryl and heteroaryl iodides is described. The transformation also proceeds with activated aryl bromides, but in this case it requires a stoichiometric amount of the catalyst for best product yields. The current reaction requires a P,N-based bidentate ligand for aryl-aryl coupling while it proceeds without external ligands for aryl-heteroaryl coupling to afford good product yields. The reaction protocol can also be applied to achieve biarylation of diiodoarenes in reasonable yields. Georg Thieme Verlag Stuttgart New York.
- Gurung, Santosh K.,Thapa, Surendra,Shrestha, Bijay,Giri, Ramesh
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p. 1933 - 1937
(2014/07/22)
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- Total syntheses of menisporphine and daurioxoisoporphine c enabled by photoredox-catalyzed direct C-H arylation of isoquinoline with aryldiazonium Salt
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Isoquinoline alkaloids are attractive natural products due to their diverse chemical structures as well as remarkable bioactivities. Herein, we report the concise total syntheses of two isoquinoline alkaloids, menisporphine and daurioxoisoporphine C, through a mild and efficient photoredox-catalyzed direct C-H arylation of isoquinoline core with aryldiazonium salt. This new strategy is complementary to the conventional isoquinoline synthesis and would provide us a useful means to achieve a more convergent and flexible approach to access diverse isoquinoline structures.
- Zhang, Jing,Chen, Jie,Zhang, Xiaoyun,Lei, Xiaoguang
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p. 10682 - 10688
(2015/02/19)
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- Direct arylation of n-heteroarenes with aryldiazonium salts by photoredox catalysis in water
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A highly effective visible light-promoted "radical-type" coupling of N-heteroarenes with aryldiazonium salts in water has been developed. The reaction proceeds at room temperature with [Ru(bpy)3]Cl 2×6 H2O as a photosensit
- Xue, Dong,Jia, Zhi-Hui,Zhao, Cong-Jun,Zhang, Yan-Yan,Wang, Chao,Xiao, Jianliang
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supporting information
p. 2960 - 2965
(2014/03/21)
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- p-toluenesulfonohydrazide as highly efficient initiator for direct C-H arylation of unactivated arenes
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p-Toluenesulfonohydrazide (PTSH) was shown to promote the highly efficient direct arylation of unactivated arenes with aryl iodides, bromides, or chlorides in the presence of potassium tert-butoxide without the assistance of any transition metals. The reaction proceeds through base-promoted homolytic aromatic substitution (BHAS) involving aryl radicals and arylradical anions as intermediates. (Chemical Equation Presented).
- Song, Qiao,Zhang, Dongmei,Zhu, Qihua,Xu, Yungen
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supporting information
p. 5272 - 5274
(2015/02/05)
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- Iodine-mediated oxidative annulation for one-pot synthesis of pyrazines and quinoxalines using a multipathway coupled domino strategy
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An efficient iodine-mediated oxidative annulation of aryl acetylenes-arylethenes-aromatic ketones with 1,2-diamines for the synthesis of pyrazines and regioselective synthesis of quinoxalines is presented. A multipathway coupled domino approach has been developed for the one-pot synthesis of 1,4-diazines with high functional group compatibility.
- Viswanadham, K. K. Durga Rao,Prathap Reddy, Muktapuram,Sathyanarayana, Pochampalli,Ravi, Owk,Kant, Ruchir,Bathula, Surendar Reddy
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p. 13517 - 13520
(2015/01/09)
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- Direct arylation of pyridines without the use of a transition metal catalyst
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A method for achieving the direct arylation of pyridines with phenylhydrazine hydrochloride was developed in this study. This new reaction proceeds readily at room temperature without the use of any transition metal catalysts. This method allows rapid access to various arylated heterocycles that are more difficult to access through traditional methods.
- Li, Yahui,Liu, Wei,Kuang, Chunxiang
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supporting information
p. 7124 - 7127
(2014/07/07)
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- A general Suzuki cross-coupling reaction of heteroaromatics catalyzed by nanopalladium on amino-functionalized siliceous mesocellular foam
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Suzuki-Miyaura cross-coupling reactions of heteroaromatics catalyzed by palladium supported in the cavities of amino-functionalized siliceous mesocellular foam are presented. The nanopalladium catalyst effectively couples not only heteroaryl halides with
- Bratt, Emma,Verho, Oscar,Johansson, Magnus J,Baeckvall, Jan-Erling
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p. 3946 - 3954
(2014/05/20)
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- Phenyl hydrazine as initiator for direct arene C-H arylation via base promoted homolytic aromatic substitution
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A simple and efficient direct radical arylation of unactivated arenes is described which uses cheap and commercially available phenyl hydrazine as an initiator. The reaction occurs through a base promoted homolytic aromatic substitution (BHAS) mechanism involving aryl radicals and aryl radical anions as intermediates and offers a practical approach for preparation of an array of substituted biaryls.
- Dewanji, Abhishek,Murarka, Sandip,Curran, Dennis P.,Studer, Armido
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supporting information
p. 6102 - 6105
(2014/01/06)
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- Efficient chromium(II)-catalyzed cross-coupling reactions between Csp 2 centers
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Low-toxicity chromium(II) chloride catalyzes at 25 C within minutes the coupling reactions of various (hetero)arylmagnesium reagents with N-heterocyclic halides, aromatic halogenated ketones or imines, and alkenyl iodides. Remarkably, much lower amounts o
- Steib, Andreas K.,Kuzmina, Olesya M.,Fernandez, Sarah,Flubacher, Dietmar,Knochel, Paul
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supporting information
p. 15346 - 15349
(2013/11/06)
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- Iron-catalyzed cross-coupling of electron-deficient heterocycles and quinone with organoboron species via innate C-H functionalization: Application in total synthesis of pyrazine alkaloid botryllazine A
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Here, we report an iron-catalyzed cross-coupling reaction of electron-deficient heterocycles and quinone with organoboron species via innate C-H functionalization. Iron(II) acetylacetonate along with oxidant (K 2S2O8) and phase-transfer catalyst (TBAB) under open flask conditions efficiently catalyzed the cross-coupling of pyrazine with arylboronic acids and gave monoarylated products in good to excellent yields. Optimized conditions also worked for other heterocylces such as quinoxalines, pyridines, quinoline, and isoquinoline as well as quinones. In addition, we demonstrated as a first example its application for the synthesis of anticancer marine pyrazine alkaloid botryllazine A.
- Singh, Parvinder Pal,Aithagani, Sravan Kumar,Yadav, Mahipal,Singh, Varun Pratap,Vishwakarma, Ram A.
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p. 2639 - 2648
(2013/04/24)
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- A highly active catalytic system for Suzuki-Miyaura cross-coupling reactions of aryl and heteroaryl chlorides in water
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An easily available Pd(OAc)2/(2-mesitylindenyl) dicyclohexylphosphine/Me(octyl)3N+Cl-/K 3PO4·3H2O catalytic system was developed and it shows high catalytic activity in the Suzuki-Miyaura cross-coupling reaction of a diverse array of aryl and heteroaryl chlorides in water. Notably, this catalytic system also works with ultra-low loading of the catalyst with high turnover numbers.
- Mao, Shu-Lan,Sun, Yue,Yu, Guang-Ao,Zhao, Cui,Han, Zhi-Jun,Yuan, Jia,Zhu, Xiaolei,Yang, Qihua,Liu, Sheng-Hua
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p. 9410 - 9417
(2013/01/15)
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- Proline catalyzes direct C-H arylations of unactivated arenes
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Several amino acids were tested to catalyze the transition-metal-free direct C-H arylation of unactivated benzene derivatives. Among them, proline was found to be an excellent catalyst for the cross-coupling between aryl halides and unactivated arenes. The reaction presumably involves an aryl radical anion as the intermediate based on several experiments. The reaction using this catalyst system offers an option toward establishing an environmentally benign and cost-effective route to biaryls.
- Tanimoro, Kouichi,Ueno, Minoru,Takeda, Kazutaka,Kirihata, Mitsunori,Tanimori, Shinji
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p. 7844 - 7849
(2013/01/15)
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- Nickel-catalyzed cross-coupling of organogold reagents
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Organogold compounds undergo nickel-catalyzed cross-coupling reactions with aryl and vinyl bromides in high yield under mild conditions. The reaction tolerates both electron-rich and electron-poor organogold complexes, and olefinic bromides undergo cross-coupling with high stereoselectivity. This novel transformation links well-established nickel catalysis with more recent developments in organogold transformations.
- Hirner, Joshua J.,Blum, Suzanne A.
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scheme or table
p. 1299 - 1302
(2011/04/22)
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- Synthesis and in vitro evaluation of botryllazine B analogues as a new class of inhibitor against human aldose reductase
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Botryllazine B analogues of diverse substitution patterns have been prepared, and their in vitro inhibitory activities against recombinant human aldose reductase (h-ALR2) evaluated. Among the 15 compounds tested, 6-(4-aminophenyl)-2-(4-hydroxyphenyl)carbonylpyrazine (7b) proved to be the most potent inhibitor, with IC50=0.91 μM. Kinetic analyses of 7b and botryllazine B (1) revealed that these inhibitors exhibit an unprecedented mixed-type inhibition on h-ALR2 with respect to the substrate d,l-glyceraldehyde, in the presence of NADPH at inhibitor concentrations near the IC50 values.
- Saito, Ryota,Tokita, Mai,Uda, Keisuke,Ishikawa, Chikako,Satoh, Mitsutoshi
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experimental part
p. 3019 - 3026
(2009/06/18)
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- Gold(I)-catalyzed direct C-H arylation of pyrazine and pyridine with aryl bromides
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An efficient procedure for the direct C-H arylation of electron-poor aromatics such as pyrazine and pyridine with aryl bomides is described. In the presence of catalytic amount of Cy3PAuCl and with the use of t-BuOK as base, pyrazine undergoes the direct C-H arylation with aryl bromides at 100 °C, and the yields of the arylated products depend on the nature of aryl bromides. In the cases of electron-rich aryl bromides used, the arylated pyrazines can be obtained in good to high yields. For electron-poor aryl bromides, the addition of AgBF4 is the crucial point to accelerate the coupling reaction to give the arylated products in moderate yields. Pyridine also reacts with electron-rich aryl bromides catalyzed by Cy3PAuCl to give a mixture of arylated regioisomers in moderate yield. However, in order to realize the direct C-H arylation of pyridine with electron-poor aryl bromides, the addition of silver salt as additive and a milder reaction temperature (60 °C) are required.
- Li, Ming,Hua, Ruimao
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supporting information; experimental part
p. 1478 - 1481
(2009/06/08)
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- Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species
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In situ mixtures of CdCl2TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2-TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt2, CO2Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Fivemembered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.
- Snegaroff, Katia,L'Helgoual'ch, Jean-Martial,Bentabed-Ababsa, Ghenia,Nguyen, Tan Tai,Chevallier, Floris,Yonehara, Mitsuhiro,Uchiyama, Masanobu,Derdour, Aicha,Mongin, Florence
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experimental part
p. 10280 - 10290
(2010/04/24)
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- Potassium t-butoxide alone can promote the biaryl coupling of electron-deficient nitrogen heterocycles and haloarenes
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(Chemical Equation Presented) The biaryl coupling of electron-deficient nitrogen heterocycles and haloarenes can be promoted by potassium t-butoxide alone, without the addition of any exogenous transition metal species. Electron-deficient nitrogen heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, and quinoxaline are arylated with haloarenes. Control experiments support a radical-based mechanism. Taking these findings into account, radical processes may be partially involved in the reported transition-metal-catalyzed arylation reactions employing t-butoxide bases and haloarenes under elevated temperatures or under microwave irradiation.
- Yanagisawa, Shuichi,Ueda, Kirika,Taniguchi, Tadashi,Itami, Kenichiro
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supporting information; scheme or table
p. 4673 - 4676
(2009/05/13)
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- Use of N-oxide compounds in coupling reactions
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Metal-catalyzed coupling process comprising reacting a compound of general formula 1 with a compound A-X, to obtain a compound of general formula 2, which may further be converted to a compound of general formula 3
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Page/Page column 15; 26
(2008/12/05)
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- Palladium-catalyzed cross-coupling reactions of diazine N-oxides with aryl chlorides, bromides, and iodides
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New aspects of N-oxides: Pyrazine, pyridazine, and pyrimidine N-oxides are regioselectively arylated with aryl iodides, bromides, and chlorides in the presence of a palladium catalyst (see scheme). The resulting products can be deoxygenated in high yield
- Leclerc, Jean-Philippe,Fagnou, Keith
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p. 7781 - 7786
(2007/10/03)
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- Aryl-aryl bonds formation in pyridine and diazine series. Diazines part 41
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The synthesis of several symmetrical polyaromatic compounds with pyridine or diazine units has been achieved by homocoupling of aryl halides with Pd(OAc)2 as catalyst. Cross-coupling reactions of aryl Grignard reagents with Fe(acac)3 as catalyst allowed the synthesis of various unsymmetrical polyaryl- or polyheteroaryl compounds with π-deficient rings.
- Boully, Ludovic,Darabantu, Mircea,Turck, Alain,Ple, Nelly
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p. 1423 - 1428
(2007/10/03)
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- A novel synthetic method for 2-arylmethyl substituted imidazolines and imidazoles from 2-aryl-1,1-dibromoethenes
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Various 2-arylmethylimidazolines were prepared by treating readily available 2-aryl-1,1-dibromoethenes with ethylenediamine under mild conditions and further converted into the corresponding imidazoles smoothly with Swern oxidation. Graphical Abstract
- Huh, Dal Ho,Ryu, Hoejin,Kim, Young Gyu
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p. 9857 - 9862
(2007/10/03)
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- Pyrazole and Isoxazole Derivatives as New, Potent, and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors
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In a previous paper, we reported the N-hydroxyformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor. Despite its attraction as a potential therapeutic agent for cerebral diseases, the preparation of an injectable formulation
- Nakamura, Toshio,Sato, Masakazu,Kakinuma, Hiroyuki,Miyata, Noriyuki,Taniguchi, Kazuo,Bando, Kagumi,Koda, Ayumi,Kameo, Kazuya
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p. 5416 - 5427
(2007/10/03)
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- Phenylpyrazine derivatives and thrombolytic agent
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Novel phenylpyrazine derivatives of the following general formula: STR1 (where R1 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a hydroxyl group; and R2 is a halogen atom, a lower alkyl group, a low
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