- Ruthenium(ii)-catalyzed chemoselective deacylative annulation of 1,3-diones with sulfoxonium ylides: Via C-C bond activation
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The first successful example of deacylative annulation of 1,3-diones with sulfoxonium ylides was achieved through Ru(ii)-catalyzed C-C bond activation. The excellent chemoselectivity and broad substrate scope render this method a practical and versatile approach for the preparation of (hetero)aryl and alkenyl substituted furans, which are valuable units in many biologically active compounds and functional materials. A preliminary mechanistic study reveals that this process involves a deacylative α-ruthenation to generate key alkyl Ru(ii) intermediates with the release of a benzoic acid fragment.
- Wen, Si,Lv, Weiwei,Ba, Dan,Liu, Jing,Cheng, Guolin
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- Synthesis of Polysubstituted Furans through Electrochemical Selenocyclization of Homopropargylic Alcohols
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The current method represents an electrochemically driven synthetic route to access polysubstituted selenofuran derivatives through the diselenide-promoted cyclization of homopropargyl alcohols. The tandem electro-oxidative transformation operates at ambi
- Maiti, Debabrata,Halder, Atreyee,Sasidharan Pillai, Aswathy,De Sarkar, Suman
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p. 16084 - 16094
(2021/10/20)
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- Decarboxylative Suzuki-Miyaura coupling of (hetero)aromatic carboxylic acids using iodine as the terminal oxidant
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A novel methodology for the decarboxylative Suzuki-Miyaura-type coupling has been established. This process uses iodine or a bromine source as both the decarboxylation mediator and the terminal oxidant, thus avoiding the need for stoichiometric amounts of transition metal salts previously required. Our new protocol allows for the construction of valuable biaryl architectures through the coupling of (hetero)aromatic carboxylic acids with arylboronic acids. The scope of this decarboxylative Suzuki reaction has been greatly diversified, allowing for previously inaccessible non-ortho-substituted aromatic acids to undergo this transformation. The procedure also benefits from low catalyst loadings and the absence of stoichiometric transition metal additives.
- Quibell, Jacob M.,Duan, Guojian,Perry, Gregory J.P.,Larrosa, Igor
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supporting information
p. 6445 - 6448
(2019/06/07)
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- Synthetic method for diaryl furan compound
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The invention relates to a synthetic method for a diaryl furan compound with a formula (6) which is described in the specification. The synthetic method has a reaction route as shown in the specification. The synthetic method comprises the following steps: S1: allowing a compound with a formula (1) and a compound with a formula (2) to react in an organic solvent in the presence of a palladium catalyst, an organic ligand, an oxidant and an acidic compound, and after completion of the reaction, carrying out post-treatment so as to obtain a compound with a formula (3); S2, allowing the compound with the formula (3) to generate a self-cyclization reaction in an organic solvent in the presence of a catalyst, and after completion of the reaction, carrying out post-treatment so as to obtain a compound with a formula (4); and S3, allowing the compound with the formula (4) and a compound with a formula (5) to react in a solvent in the presence of a palladium catalyst, an organic ligand and an acidic compound at the atmosphere of oxygen, and after completion of the reaction, carrying out post-treatment so as to obtain a compound with a formula (6). The method provided by the invention realizes creative optimization in a plurality of technical characteristics through all steps, provides a novel synthetic method and a synthetic route for preparation of the compound, and has good industrialprospects and potential application values.
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- Epoxy-containing skeleton nitrile compound and synthesis method thereof
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The invention relates to an epoxy-containing skeleton nitrile compound as shown in the following formula (4) and a synthesis method thereof. The synthesis method adopts the following reaction route: FORMULA, and comprises the following steps: S1: reacting a compound of a formula (1) with a compound of formula (2) in an organic solvent in the presence of a palladium catalyst, an organic ligand, anoxidizing agent and an acidic compound, performing post-treatment after finishing reaction to obtain a compound of formula (3); and S2: performing self-cyclization reaction on the compound of formula(3) in the organic solvent in the presence of the oxidizing agent, performing post-treatment after finishing reaction to obtain a compound of formula (4). The method creatively optimizes multiple technical features in each step so as to provide a novel synthesis method and synthesis route for preparation of such compounds and have excellent industrial prospects and potential application values.
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- A synthetic method of furan derivatives
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The invention relates to a synthetic method of furan derivatives shown as a formula (6) as follows. The synthetic route of the method is shown in the specification. The method includes S1) allowing acompound shown as a formula (3) in an organic solvent to self-cyclize with the existence of an oxidant, and performing after-treatment when the reaction is finished to obtain a compound of a formula (4); and S2) reacting the compound of the formula (4) and a compound of a formula (5) in an oxygen atmosphere with the existence of a palladium catalyst, an organic ligand and an acidic compound in a solvent, and performing after-treatment after the reaction is finished to obtain a compound of the formula (6). A plurality of technical characteristics of each step are innovatively optimized in the method, and the brand-new synthetic method and synthetic route for preparing the compounds of this type are provided. The method has a good industrial prospect and good application value.
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- A co-operative effect of visible light photo-catalysis and CoFe2O4 nanoparticles for green synthesis of furans in water
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A novel approach to poly-functionalized furan synthesis is disclosed via oxidative decarboxylative [3+2] cycloaddition using co-operative catalysis by visible light and CoFe2O4 nanoparticles under ambient reaction conditions with water as a solvent. Although the reported method is efficient without catalyst in the presence of visible light (70% yield in 4 h at rt), the use of catalyst not only increases the yield (91%) but also accelerates the conversion rate (2 h at rt).
- Verma, Fooleswar,Singh, Puneet K.,Bhardiya, Smita R.,Singh, Manorama,Rai, Ankita,Rai, Vijai K.
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supporting information
p. 4937 - 4942
(2017/07/12)
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- Copper-Catalyzed Regioselective Synthesis of Multisubstituted Furans by Coupling between Ketones and Aromatic Olefins
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A regioselective synthesis of multisubstituted furan derivatives has been developed via Cu(II)-catalyzed intermolecular annulation of aryl ketones with a wide range of aromatic olefins under ambient air in good yields. This protocol is applicable to both cyclic and acyclic aryl ketones.
- Dey, Amrita,Ali, Md Ashif,Jana, Sourav,Hajra, Alakananda
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p. 4812 - 4818
(2017/05/12)
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- Regioselective Synthesis of Multisubstituted Furans via Copper-Mediated Coupling between Ketones and β-Nitrostyrenes
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A copper-mediated intermolecular annulation of alkyl ketones and β-nitrostyrenes has been developed for the regioselective synthesis of multisubstituted furan derivatives in good yields. This protocol is applicable to both cyclic and acyclic ketones. (Che
- Ghosh, Monoranjan,Mishra, Subhajit,Hajra, Alakananda
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p. 5364 - 5368
(2015/05/27)
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- Successively recycle waste as catalyst: A one-pot wittig/1,4-reduction/paal-knorr sequence for modular synthesis of substituted furans
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A one-pot tandem Wittig/conjugate reduction/Paal-Knorr reaction is reported for the synthesis of di- or trisubstituted furans. This novel sequence first demonstrates the possibility of successively recycling waste from upstream steps to catalyze downstream reactions.
- Chen, Long,Du, Yi,Zeng, Xing-Ping,Shi, Tao-Da,Zhou, Feng,Zhou, Jian
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p. 1557 - 1560
(2015/03/30)
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- A highly efficient synthesis of 2,5-disubstituted furans from enyne acetates catalyzed by lewis acid and palladium
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A highly efficient synthesis of a wide range of 2,5-disubstituted furans from enyne acetates is described. The reactions are conducted by using Lewis acid and palladium catalyst and provide symmetrical and unsymmetrical products in good to excellent yields, with broad substrate scope, including a variety of aromatic and aliphatic substituents in the 2- and 5-position of the furan ring.
- Chen, Zheng-Wang,Luo, Miao-Ting,Wen, Yue-Lu,Ye, Min,Zhou, Zhong-Gao,Liu, Liang-Xian
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supporting information
p. 2341 - 2344
(2015/08/06)
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- A sequential synthesis of substituted furans from aryl alkynes and ketones involving a cerium(IV) ammonium nitrate (CAN)-mediated oxidative cyclization
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A convenient, two-step synthesis of substituted furans from readily available aryl alkynes and ketones is reported. The furan-forming oxidative cyclization is mediated by the combination of cerium(IV) ammonium nitrate and potassium bromide and can be carried out in an open flask.
- Undeela, Sridhar,Ramchandra, Joshi P.,Menon, Rajeev S.
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p. 5667 - 5670
(2014/12/12)
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- Gold-catalyzed C(sp3)-H/C(sp)-H coupling/cyclization/oxidative alkynylation sequence: A powerful strategy for the synthesis of 3-alkynyl polysubstituted furans
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In sharp contrast to the gold-catalyzed reactions of alkynes/allenes with nucleophiles, gold-catalyzed oxidative cross-couplings and especially C-H/C-H cross-coupling have been under represented. By taking advantage of the unique redox property and carbophilic π acidity of gold, this work realizes the first gold-catalyzed direct C(sp3)-H alkynylation of 1,3-dicarbonyl compounds with terminal alkynes under mild reaction conditions, with subsequent cyclization and in situ oxidative alkynylation. A variety of terminal alkynes including aryl, heteroaryl, alkenyl, alkynyl, alkyl, and cyclopropyl alkynes all successfully participate in the domino reaction. The protocol offers a simple and region-defined approach to 3-alkynyl polysubstituted furans. Pure and simple: The first gold-catalyzed C(sp3)-H/C(sp)-H cross-coupling/cyclization/oxidative alkynylation sequence of 1,3-dicarbonyl compounds reacting with terminal alkynes has been achieved under mild reaction conditions by taking advantage of the unique redox property and carbophilic π acidity of gold. Ultimately, 3-alkynyl polysubstituted furans are synthesized concisely and regiospecifically from simple starting materials.
- Ma, Yuanhong,Zhang, Shuai,Yang, Shiping,Song, Feijie,You, Jingsong
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supporting information
p. 7870 - 7874
(2014/08/05)
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- Tandem reaction of 1,2-allenic ketone with α-halo ketone or α-halo ester in water: An efficient and sustainable synthesis of 1,3,4′-tricarbonyl compounds
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An efficient and sustainable synthesis of the otherwise difficult to obtain 1,3,4′-tricarbonyl compounds through a water mediated, TBAF·3H2O promoted unprecedented tandem reaction of 1,2-allenic ketone with α-halo ketone or α-halo ester has been developed. Remarkably enhanced reactivity and improved chemoselectivity by using water as the reaction medium was observed. The 1,3,4′-tricarbonyl compounds facilitate further versatile transformations, which underscores the importance of these products as synthetic intermediates. The Royal Society of Chemistry.
- Fan, Xuesen,He, Yan,Cui, Liangyan,Zhang, Xinying,Wang, Jianji
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p. 3218 - 3223
(2011/12/16)
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- Zinc-catalyzed cycloisomerizations. Synthesis of substituted furans and furopyrimidine nucleosides
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(Chemical Equation Presented) 5-Endo-dig cycloisomerization of 1,4- and 1,2,4- mostly aryl-substituted but-3-yn-1-ones in the presence of a catalytic amount of zinc chloride etherate (10 mol %) in dichloromethane at room temperature gave 2,5-di- and 2,3,5
- Sniady, Adam,Durham, Audrey,Morreale, Marco S.,Marcinek, Andrzej,Szafert, Slawomir,Lis, Tadeusz,Brzezinska, Krystyna R.,Iwasaki, Takanori,Ohshima, Takashi,Mashima, Kazushi,Dembinski, Roman
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p. 5881 - 5889
(2008/12/21)
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- Room temperature zinc chloride-catalyzed cycloisomerization of alk-3-yn-1-ones: Synthesis of substituted furans
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5-Endo-dig cycloisomerization of 1,4-di- and 1,2,4-trisubstituted but-3-yn-1-ones in the presence of a catalytic amount of zinc chloride (10 mol %) in dichloromethane at room temperature (22 °C) provides 2,5-di- and 2,3,5-trisubstituted furans in high yie
- Sniady, Adam,Durham, Audrey,Morreale, Marco S.,Wheeler, Kraig A.,Dembinski, Roman
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p. 1175 - 1178
(2008/01/04)
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- Palladium-catalyzed tandem dimerization and cyclization of acetylenic ketones: A convenient method for 3,3′-bifurans using PdCl2(PPh3)2
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Alkynones undergo tandem dimerization and cyclization in the presence of PdCl2(PPh3)2 and triethylamine in tetrahydrofuran at room temperature to give 3,3′-bifurans predominantly. Other palladium catalysts while under similar conditions, by rearrangement, lead to 2,5-disubstituted furans. This distinguished property of PdCl2(PPh3)2 has been attributed to the involvement of hydridopalladium halide. This method provides a simpler route to a variety of furans and a regioselective synthesis of polysubstituted 3,3′-bifurans using easily accessible acetylenic ketones.
- Jeevanandam,Narkunan,Ling
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p. 6014 - 6020
(2007/10/03)
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- Preparations of Furans from α-Bromo Ketones and Enol Ethers Catalyzed by a Rhenium(I) Nitrogen Complex
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By the catalytic use of a rhenium(I) nitrogen complex, [ReCl(N2)(PMe2Ph)4], α-keto radicals are generated from α-bromo ketones and react with vinyl ethers and silyl enol ethers intermolecularly. Various substituted furans, including tetrasubstituted furans such as furoguaiacin, are prepared by this method.
- Koga, Yuji,Kusama, Hiroyuki,Narasaka, Koichi
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p. 475 - 482
(2007/10/03)
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- Further reactions of furans with trithiazyl trichloride; mechanistic considerations
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The reaction of 2,5-diarylfurans with trithiazyl trichloride 1 to give 5-aroyl-3-arylisothiazoles in a useful one-step synthesis of isothiazoles has been extended to both weakly and strongly polarised unsymmetrical 2,5-diarylfurans. These react in an entirely analogous manner; the more electron releasing aryl group becomes incorporated into the 5-aroyl group of the isothiazole as the exclusive (strong polarisation) or the major (weak polarisation) product. However, with 3-bromo-2-(4-methoxyphenyl)-5-(4-nitrophenyl)-furan 7, where the more reactive furan β-position is now substituted, this regiospecificity is reversed (to give isothiazole 8). When one of the α-aryl groups in the furan is replaced by methyl the same regiospecific isothiazole formation is now accompanied by some ring and side chain chlorination (15 → 16 + 17 + 18). All of these results can be explained by mechanisms (Schemes 2 and 5) which involve initial electrophilic attack of the furan to give a β-thiazyl derivative. This highly reactive (nitrenoid) substituent then induces a novel opening of the furan ring 21 to give a highly delocalised intermediate 22 which recyclises to the isothiazole.
- Rees, Charles W.,Yue, Tai-Yuen
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p. 2247 - 2252
(2007/10/03)
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- Palladium-Catalyzed Rearrangement of 2-Alkynyl Aryl Ketones to Substituted Furans
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1,4-Diaryl- and 1,4-diaryl-2-alkyl-3-butyn-1-ones can be rearranged catalytically by treatment with Pd(dba)2/PPh3 to give 2,5-substituted and 2,3,5-trisubstituted furans in 26-38percent yields.
- Sheng, Huaiyu,Lin, Shouyuan,Huang, Yaozeng
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p. 1022 - 1023
(2007/10/02)
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