- Indium-mediated allylation of acyl cyanides in aqueous media: A convenient synthesis of β,γ-unsaturated ketones
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The indium-mediated allylation reaction of acyl cyanides with allyl halides in aqueous media afforded a variety of β,γ-unsaturated ketones in moderate to good yields under mild and neutral conditions.
- Yoo, Byung Woo,Choi, Kwang Hyun,Lee, Sung Jae,Nam, Ghil Soo,Chang, Kwan Young,Kim, Sung Hoon,Kim, Joong Hyup
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- Ytterbium mediated coupling of α-oxonitriles with allylbromides: Convenient synthesis of β,γ-unsaturated ketones
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A new and efficient method for the preparation of β,γ-unsaturated ketones has been achieved by the simple reaction of an acyl cyanide with ailyl, crotyl and prenyl bromides and ytterbium metal in absolute tetrahydrofuran.
- Gohain, Mukut,Gogoi, Baikuntha J.,Prajapati, Dipak,Sandhu, Jagir S.
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- Microwave-assisted catalytic allylation of aldehydes promoted by a mesoporous silica-supported BINOL ligand in solid media
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An efficient and operationally simple method for catalytic allylation has been developed and its application in the microwave-assisted catalytic allylation of aldehydes in solid media was investigated. The Royal Society of Chemistry.
- Liu, Guohua,Gao, Yan,Lu, Xiaoquan,Liu, Mouming,Zhang, Fang,Li, Hexing
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- A new method for the synthesis of acyltitanium complexes and their application to copper-mediated acylmetallation of carbon-carbon multiple bonds in aqueous media
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Treatment of α,β-unsaturated carbonyl compounds or methyl propargyl ether with acylchlorobis(cyclopentadienyl)titanium in the presence of Methylamine and a copper salt in aqueous THF resulted in acylation of the carbon-carbon multiple bond, yielding the c
- Han, Zhenfu,Fujioka, Takuma,Usugi, Shin-Ichi,Yorimitsu, Hideki,Shinokubo, Hiroshi,Oshima, Koichiro
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- Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton
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An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).
- Shikari, Amit,Mandal, Koushik,Chopra, Deepak,Pan, Subhas Chandra
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- Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes
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A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.
- Fu, Xiao-Yang,Si, Ya-Feng,Qiao, Li-Peng,Zhao, Yu-Fen,Chen, Xiao-Lan,Yu, Bing
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p. 574 - 580
(2021/11/13)
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- Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines
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A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.
- He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng
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- Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems
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A nickel-catalyzed 1,2-diarylation of alkenyl ketones with aryl iodides and arylboronic esters is reported. Ketones with a variety of substituents serve as effective directing groups, offering high levels of regiocontrol. A representative product is diversified into a wide range of useful products that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding mode of the substrate, and Hammett analysis reveals the effect of electronic factors on initial rates.
- Apolinar, Omar,Derosa, Joseph,Engle, Keary M.,Karunananda, Malkanthi K.,Kleinmans, Roman,Li, Zi-Qi,Tran, Van T.,Wisniewski, Steven R.
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p. 5311 - 5316
(2021/07/26)
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- Electrochemical Chalcogenation of β,γ-Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines
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The current report represents a transition-metal-free synthesis of oxazoline and isoxazoline derivatives by a tandem electro-oxidative chalcogenation-cyclization process. Both C?Se and C?S bond-forming protocols were developed without using any external oxidant and the reaction was performed at room temperature, open to the air. Using this methodology, 29 substituted oxazoline and 16 substituted isoxazoline derivatives were synthesized with up to 91% isolated yield. (Figure presented.).
- Baidya, Mrinmay,De Sarkar, Suman,Mahanty, Kingshuk,Maiti, Debabrata,Mallick, Samrat
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- Enantioselective Synthesis of Isoxazolines Enabled by Palladium-Catalyzed Carboetherification of Alkenyl Oximes
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Reported here is a highly efficient Pd/Xiang-Phos catalyzed enantioselective carboetherification of alkenyl oximes with either aryl or alkenyl halides, delivering various chiral 3,5-disubstituted and 3,5,5-trisubstituted isoxazolines in good yields with u
- Chen, Mingjie,Li, Wenbo,Wang, Lei,Wang, Yuzhuo,Zhang, Junliang,Zhang, Kenan
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p. 4421 - 4427
(2020/02/11)
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- Copper-catalyzed asymmetric cyanation of alkenes via carbonyl-assisted coupling of alkyl-substituted carbon-centered radicals
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Based on a copper-catalyzed radical relay strategy, the first copper-catalyzed asymmetric cyanation of alkyl-substituted alkenes has been developed. The reaction, featuring mild reaction conditions and excellent functional group compatibilities, provides
- Zhou, Song,Zhang, Guoyu,Fu, Liang,Chen, Pinhong,Li, Yibiao,Liu, Guosheng
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p. 6299 - 6303
(2020/10/02)
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- Copper-Catalyzed Aerobic Cyclization of β,γ-Unsaturated Hydrazones with Concomitant CC Bond Cleavage
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A Cu-catalyzed aerobic oxidative cyclization of β,γ-unsaturated hydrazones for the preparation of pyrazole derivatives has been developed. The hydrazonyl radical promoted the cyclization, along with a concomitant CC bond cleavage of β,γ-unsaturated hydrazones. This process has been verified via several control experiments, including a radical-trapping study, an 18O-labeling method, and the identification of the possible byproducts. The advantages of this reaction include operational simplicity, a broad reaction scope, and a mild selective reaction process.
- Fan, Zhenwei,Feng, Jiahao,Hou, Yuchen,Rao, Min,Cheng, Jiajia
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p. 7981 - 7985
(2020/11/02)
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- Ruthenium-Catalyzed Direct Transformation of Alkenyl Oximes to 5-Cyanated Isoxazolines: A Cascade Approach Based on Non-Stabilized Radical Intermediate
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A ruthenium-catalyzed ammoxidation of alkenyl oximes under mild and neutural condtions is described. In this method, tert-butyl nitrite plays a dual role, acting as an oxidant as well as a nitrogen source. This reaction avoids using any toxic radical initiators or cyanide reagents. This convenient and practical method offers an easy access to 5-cyanated isoxazolines in good to high yields, and shows good functional group tolerance and high efficiency. It is rather remarkable that this new reaction provides a strategically distinct approach based on non-stabilized radical intermediate and constructs C–O and C≡N triple bonds in a single-step. Moreover, the difunctionalization of unactivated olefins bearing oximes has been realized.
- Wang, Dan-Jun,Chen, Bei-Yi,Wang, Yi-Qi,Zhang, Xiao-Wei
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p. 1342 - 1346
(2018/04/02)
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- Copper-Promoted 6- endo-trig Cyclization of β,γ-Unsaturated Hydrazones for the Synthesis of 1,6-Dihydropyridazines
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A novel and efficient strategy for the synthesis of 1,6-dihydropyridazines via copper-promoted 6-endo-trig cyclization of readily available β,γ-unsaturated hydrazones have been developed. A series of 1,6-dihydropyridazines have been synthesized by this method with good yields, high functional group tolerance, and remarkable regioselectivity under mild conditions. Importantly, the 1,6-dihydropyridazines can be efficiently converted to biologically important pyridazines in the presence of NaOH.
- Guo, Yong-Qiang,Zhao, Mi-Na,Ren, Zhi-Hui,Guan, Zheng-Hui
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p. 3337 - 3340
(2018/06/11)
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- Copper-mediated oxysulfonylation of alkenyl oximes with sodium sulfinates: a facile synthesis of isoxazolines featuring a sulfone substituent
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A novel and efficient Cu(OAc)2-mediated oxysulfonylation of alkenyl oximes with sodium sulfonates was developed. The reactions are easy to conduct, occur under mild conditions, and form a broad range of sulfone-substituted isoxazolines in good yields.
- Wang, Li-Jing,Chen, Manman,Qi, Lin,Xu, Zhidong,Li, Wei
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p. 2056 - 2059
(2017/02/15)
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- Lewis Acid Catalyzed [3+3] Annulation of Donor–Acceptor Cyclopropanes with γ-Hydroxyenones: Access to Highly Functionalized Tetrahydropyrans
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Donor–acceptor cyclopropanes were engaged in a [3+3]-annulation reaction with γ-hydroxyenones. Sc(OTf)3was found to be the best catalyst, and 2,4,4,5-tetrasubstituted tetrahydropyran products were obtained in good yields under mild reaction con
- Mondal, Keshab,Pan, Subhas Chandra
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p. 534 - 537
(2017/02/05)
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- Palladium(0)-mediated cyclization-coupling of β,γ-unsaturated oximes and aryl iodides
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The tandem palladium(0)-mediated nucleometalation-cross coupling of β,γ-unsaturated oximes with aryl iodides has been shown to provide the expected 3,5-disubstituted 2-isoxazolines in acceptable yields (11-78%). The addition of a weak base is required for product formation. Some influence on the yield of the reaction is noted in the electronic character of the aryl iodide used in the reaction. Exploration of the substitution patterns on the reactants has led to a proposed mechanism involving a palladium(II)-catalyzed nucleometalation/cyclization followed by reductive elimination of palladium(0) with concomitant coupling to an arene.
- Mikesell, Joshua,Mosher, Michael D.
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p. 1011 - 1013
(2016/02/16)
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- Organocatalytic Redox Isomerization of Electron-Deficient Allylic Alcohols: Synthesis of 1,4-Ketoaldehydes
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An organocatalytic redox isomerization strategy has been developed for the synthesis of 1,4-ketoaldehydes. DABCO was found to be the best catalyst for the isomerization of -hydroxy enones. With 20 mol % of DABCO as catalyst and DMSO as the solvent high yi
- Mondal, Keshab,Mondal, Buddhadeb,Pan, Subhas Chandra
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p. 4835 - 4840
(2016/07/06)
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- Metal-Free Autoxidative Nitrooxylation of Alkenyl Oximes with Molecular Oxygen
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A metal-free aerobic autoxidative nitrooxylation of alkenyl oximes mediated by tert-butyl nitrite is described. Molecular oxygen is used as the oxidizing reagent, avoiding use of organic trapping reagents such as 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMP
- Zhang, Xiao-Wei,Xiao, Zu-Feng,Zhuang, Yan-Jun,Wang, Mei-Mei,Kang, Yan-Biao
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p. 1942 - 1945
(2016/07/06)
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- Transition-metal-free oxychlorination of alkenyl oximes:: In situ generated radicals with tert -butyl nitrite
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Oxychlorination of alkenyl oximes is harder compared to the analogous oxybromination or oxyiodination because of the difficulty associated with the formation of chlorine cations or radicals. A transition-metal-free oxychlorination of alkenyl oximes has be
- Zhang, Xiao-Wei,Xiao, Zu-Feng,Wang, Mei-Mei,Zhuang, Yan-Jun,Kang, Yan-Biao
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p. 7275 - 7281
(2016/08/05)
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- Oxime-mediated oxychlorination and oxybromination of unactivated olefins
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An oxime-mediated oxychlorination and oxybromination of unactivated olefins relying on palladium catalysis has been developed. A wide range of chlorinated and brominated isoxazolines has been synthesized in moderate to good yields. To demonstrate the value of the method, the brominated isoxazoline has been further converted to other useful synthetic feedstock.
- Dong, Kui-Yong,Qin, Hai-Tao,Liu, Feng,Zhu, Chen
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p. 1419 - 1422
(2015/03/04)
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- Iodine(III)-Mediated Oxy-fluorination of Alkenyl Oximes: An Easy Path to Monofluoromethyl-Substituted Isoxazolines
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A highly regioselective intramolecular oxy-fluorination of alkenyl oximes was achieved. This new transformation represents an efficient method for the preparation of monofluoromethyl-substituted isoxazolines. The synthetic application of the oxy-fluorinat
- Kong, Weidong,Guo, Quanping,Xu, Zhaoqing,Wang, Guoqiang,Jiang, Xianxing,Wang, Rui
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p. 3686 - 3689
(2015/08/18)
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- Copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates: A facile synthesis of 2-arylpyrroles
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A novel and facile copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates for the synthesis of 2-arylpyrroles has been developed. The reaction tolerates a range of functional groups and is a practical procedure for rapid synthesis of 2-arylpyrroles in high yields under mild conditions. the Partner Organisations 2014.
- Du, Wei,Zhao, Mi-Na,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
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p. 7437 - 7439
(2014/07/07)
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- Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin
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A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).
- Dong, Kui-Yong,Qin, Hai-Tao,Bao, Xing-Xing,Liu, Feng,Zhu, Chen
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p. 5266 - 5268
(2015/01/09)
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- Synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones
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Developing olefin isomerization reactions to reach kinetically controlled Z-alkenes is challenging because formation of trans-alkenes is thermodynamically favored under the traditional catalytic conditions using acids, bases, or transition metals as the catalysts. A new synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones to α,β-unsaturated ketones was developed, providing an easy and efficient way to access various Z-enones.
- Zhuo, Lian-Gang,Yao, Zhong-Ke,Yu, Zhi-Xiang
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p. 4634 - 4637
(2013/10/08)
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- Δ2-isoxazolines from β,γ-unsaturated oximes
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3,5-Disubstituted Δ2-isoxazolines can be prepared using the palladium-mediated nucleometalation/ methoxycarbonylation of β,γ-unsaturated oximes. This novel route to this class of compounds is tolerant of a wide variety of functionality in the s
- Mosher, Michael D.,Emmerich, Laura G.,Frost, Katherine S.,Anderson, Benjamin
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p. 535 - 539
(2007/10/03)
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- A novel rearrangement of chromium allyloxy(aryl)carbene complexes catalyzed by Pd(0)
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Chromium allyloxy(aryl)carbene complexes undergo formal [2,3]-or [1,2]-sigmatropic rearrangement by the catalytic use of Pd(PPh3)4 under CO atmosphere. The reaction is considered to proceed via palladium aroyl π-allyl complex, which is converted to the co
- Sakurai, Hidehiro,Tanabe, Katsuhiko,Narasaka, Koichi
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- Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones
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Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding α-(benzotriazol-1-yl)aryl ethyl ethers 7 in good yield.The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation.Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), α-hydroxyalkyl (12 and 13), α-aminoalkyl (14) and acyl (15) substituents.
- Katritzky, Alan R.,Lang, Hengyuan,Wang, Zuoquan,Zhang, Zhongxing,Song, Huimin
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p. 7619 - 7624
(2007/10/03)
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- Photochemically Induced Single Electron Transfer Reactions of Benzils with Allylstannane. Direct Observation of Reactive Intermediates by ESR Method
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Allthough the photochemically induced reaction of benzil with allyltrimethylstannane in benzene afforded α-allylbenzoin as a major product, benzil did not react thermally with the same reagent.An ESR observation disclosed that the benzil anion radical ion
- Maruyama, Kazuhiro,Matano, Yoshihiro
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p. 2218 - 2223
(2007/10/02)
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