- Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles
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The first example of the Pd-catalyzed addition of organoboron reagents to dinitriles, as an efficient means of preparing 2,5-diarylpyrroles and 2,6-diarylpyridines, has been discussed here. Furthermore, the highly selective carbopalladation of dinitriles with organoboron reagents to give long-chain ketonitriles has been developed as well. Based on the broad scope of substrates, excellent functional group tolerance, and use of commercially available substrates, the Pd-catalyzed addition reaction of arylboronic acid and dinitriles is expected to be significant in future synthetic procedures.
- Qi, Linjun,Li, Renhao,Yao, Xinrong,Zhen, Qianqian,Ye, Pengqing,Shao, Yinlin,Chen, Jiuxi
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supporting information
p. 1097 - 1108
(2020/01/22)
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- Visible-Light-Induced C (sp3)-H Functionalization of Tosylhydrazones: Synthesis of Polysubstituted Pyrroles under Metal-Free Conditions
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Iodine catalyzed C (sp3)-H functionalization of tosylhydrazones with β-enamino esters under visible light irradiation for the synthesis of trisubstituted pyrroles has been described. The present method is also applicable to α- substituted tosyl
- Kumar Reddy, N. Naresh,Rawat, Deepa,Adimurthy, Subbarayappa
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p. 9412 - 9421
(2018/07/30)
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- Divergent Iron-Catalyzed Coupling of O-Acyloximes with Silyl Enol Ethers
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An iron-catalyzed coupling reaction of O-acyloximes and O-benzoyl amidoximes with silyl enol ethers is reported. The protocol provides access to functionalized pyrroles, 1,6-ketonitriles, pyrrolines and imidazolines via carbon-centered radicals generated from an initially formed iminyl radical. The intramolecular cyclization and ring-opening processes of the iminyl radical take place preferentially over reactions that proceed through a 1,3-hydrogen transfer, providing insights into iron-catalyzed reactions with oxime derivatives. The cheap and environmentally friendly iron catalyst, the broad substrate scope and the functional group compatibility make this protocol useful for synthesis of valuable nitrogen-containing products.
- Yang, Hai-Bin,Selander, Nicklas
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p. 1779 - 1783
(2017/02/15)
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- Copper-Catalyzed Coupling of 2-Siloxy-1-alkenes and Diazocarbonyl Compounds: Approach to Multisubstituted Furans, Pyrroles, and Thiophenes
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We report herein copper(II)-catalyzed cyclization reactions of silyl enol ethers derived from methyl ketones with α-diazo-β-ketoesters or α-diazoketones to afford 2-siloxy-2,3-dihydrofuran derivatives or 2,3,5-trisubstituted furans, respectively, under mild conditions. The former cyclization products serve as versatile 1,4-diketone surrogates, allowing facile preparation of 2,3,5-trisubstituted furans, pyrroles, and thiophenes.
- Tan, Wei Wen,Yoshikai, Naohiko
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p. 5566 - 5573
(2016/07/14)
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- The synthesis of pyrroles and oxazoles based on gold α-imino carbene complexes
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Cationic gold complexes of α-oximimino carbenes have been identified to react with weak nucleophiles including enol ethers and nitriles. These findings allowed us to develop the highly efficient synthesis of pyrroles and oxazoles.
- Loy, Nicole S. Y.,Choi, Subin,Kim, Sunggak,Park, Cheol-Min
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p. 7336 - 7339
(2016/06/14)
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- Visible-light-induced formal [3+2] cycloaddition for pyrrole synthesis under metal-free conditions
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A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues. A primary trial of photocascade catalysis merging energy transfer and redox neutral reactions was shown to be successful. Photo(chemistry) op: A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been established under the irradiation of visible light in the presence of an organic dye. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the formal synthesis of an inhibitor for HMG-CoA reductase.
- Xuan, Jun,Xia, Xu-Dong,Zeng, Ting-Ting,Feng, Zhu-Jia,Chen, Jia-Rong,Lu, Liang-Qiu,Xiao, Wen-Jing
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p. 5653 - 5656
(2014/06/10)
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- Synthesis of multi-substituted pyrroles using enamides and alkynes catalyzed by Pd(OAc)2 with molecular oxygen as an oxidant
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A cyclization reaction between enamides and alkynes catalyzed by palladium(ii) acetate is described. In this method, the molecular oxygen serves as an efficient oxidant for the Pd(ii)/Pd(0) catalytic cycle. The simple reaction conditions permit this methodology to be used as a general tool for the preparation of multi-substituted pyrroles.
- Xu, Yun-He,He, Tao,Zhang, Qiu-Chi,Loh, Teck-Peng
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supporting information
p. 2784 - 2786
(2014/03/21)
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- Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and 1,3-dicarbonyl compounds
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(Chemical Equation Presented) Polysubstituted N-H pyrroles with a wide variety of substituents were prepared from vinyl azides and 1,3-dicarbonyl compounds by using Mn(III) complexes as catalysts.
- Wang, Yi-Feng,Ton, Kah Kah,Chiba, Shunsuke,Narasaka, Koichi
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supporting information; scheme or table
p. 5019 - 5022
(2009/05/07)
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- Synthesis of substituted pyrroles from N-vinylic phosphazenes derived from β-amino acids and α-bromo ketones
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Synthesis of di-, tri- and tetrasubstituted pyrroles by reaction of Nvinylic phosphazenes derived from β-amino acids with α-bromo ketones is described.
- Palacios, Francisco,Herran, Esther,Rubiales, Gloria
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- Synthesis of Pyrrole Derivatives Using Thioimidates
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Dimethyl acetylenedicarboxylate, ethyl propiolate, nitro olefins, or 2-nitroalkyl acetates react with thioimidate in the presence of organic bases to give the corresponding pyrroles in moderate-to-good yields.
- Yokoyama, Masataka,Menjo, Yasuhiro,Wei, He,Togo, Hideo
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p. 2735 - 2738
(2007/10/03)
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- Oxidative Halogenation of Substituted Pyrroles with Cu(II). Part II. Bromination of some Ethyl 3-Pyrrolecarboxylates and Corresponding Acids
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Ethyl 3-pyrrolecarboxylates and their corresponding acids are brominated with copper(II) bromide.The reaction afforded at 0 deg, with high-yield nuclear monobromination.
- Petruso, S.,Caronna, S.,Sferlazzo, M.,Sprio, V.
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p. 1277 - 1280
(2007/10/02)
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