- 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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supporting information
p. 574 - 580
(2021/11/13)
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- Copper-Impregnated Magnesium-Lanthanum Mixed Oxide: A Reusable Heterogeneous Catalyst for Allylation of Aldehydes and Ketones
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Copper-impregnated magnesium-lanthanum mixed oxide [Cu(II)/Mg?La] was used as catalyst in synthesis of homoallylic alcohols from aldehydes and ketones using allyltributylstannane as the allylating source. The present protocol provides a great application
- Laha, Soumi,Likhar, Pravin R.,Pogula, Jaya,Sreedhar, B.
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supporting information
(2020/02/11)
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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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supporting information
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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supporting information
p. 2056 - 2059
(2017/02/15)
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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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supporting information
p. 7437 - 7439
(2014/07/07)
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- Homoallyl-cyclopropylcarbinyl cation manifold. Trimethylsilyl versus aryl stabilization
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(Chemical Equation Presented) A series of E- and Z-1-aryl-5-trimethylsilyl- 3-buten-1-yl trifluoroacetates were solvolyzed in CD3CO2D, and rates of reaction as well as products derived from these reactions were determined. Hammett pl
- Creary, Xavier,O'Donnell, Benjamin D.,Vervaeke, Marie
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p. 3360 - 3368
(2008/02/03)
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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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- Identification of potent type I MetAPs inhibitors by simple bioisosteric replacement. Part 2: SAR studies of 5-heteroalkyl substituted TCAT derivatives
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Systematic SAR studies on the thiazole ring 5-substituent of TCAT derivatives revealed that the introduction of a β-alkoxy or an amino group enhanced the inhibitory activity significantly. The present compounds are representative of specific Co(II)-MetAP1 inhibitors. Before the physiologically relevant metal ions for MetAPs are established, these small molecular compounds could be used as tools for detailed biological studies.
- Cui, Yong-Mei,Huang, Qing-Qing,Xu, Jie,Chen, Ling-Ling,Li, Jing-Ya,Ye, Qi-Zhuang,Li, Jia,Nan, Fa-Jun
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p. 4130 - 4135
(2007/10/03)
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- Palladium-catalyzed allylation of carbonyl compounds with various allylic compounds using In-InCl3 in aqueous media
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Various allylic compounds can be effectively applied to palladium-catalyzed allylation of carbonyl compounds via the formation of π-allylpalladium(II) intermediates and their transmetalation with indium in the presence of indium trichloride in aqueous media.
- Jang, Taeg-Su,Keum, Gyochang,Kang, Soon Bang,Chung, Bong Young,Kim, Youseung
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p. 775 - 779
(2007/10/03)
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- Oxonia-Cope rearrangement and side-chain exchange in the Prins cyclization
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(Formula Presented) TMSOAc OAc OAc 2 3 Evidence is presented here for the mechanism of the Prins cyclization of benzylic homoallylic alcohols, which shows that the outcome of the reaction is dependent upon the substituents on the aromatic ring. The presence of an electron-rich aromatic ring favors an oxonia-Cope rearrangement yielding a symmetrical tetrahydropyran as the major product formed via a side-chain exchange process. In contrast, with electron-deficient aromatic rings the expected 2,4,6-trisubstituted tetrahydropyran is formed.
- Crosby, Stuart R.,Harding, John R.,King, Clare D.,Parker, Gregory D.,Willis, Christine L.
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p. 577 - 580
(2007/10/03)
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- Magnesium-mediated carbon-carbon bond formation in aqueous media: Barbier-Grignard allylation and pinacol coupling of aldehydes
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Magnesium-mediated Barbier-Grignard type alkylation of aldehydes with alkyl halides was studied in aqueous media. The reaction of aromatic aldehydes with allyl halides is highly effective with either THF or water as the reaction solvent but poor in a mixture of THF/water. It was found that the magnesium-mediated allylation of aldehydes with allyl bromide and iodide proceeds effectively in aqueous 0.1 N HCl or 0.1 N NH4Cl. Aromatic aldehydes reacted chemoselectively in the presence of aliphatic aldehydes. An exclusive selectivity was also observed when both aliphatic and aromatic aldehyde functionalities are present in the same molecule. In the absence of allyl halides, aldehydes and ketones reacted with magnesium in aqueous 0.1 N NH4Cl to form the corresponding pinacol coupling products in high yields. The effectiveness of the pinacol reaction was strongly influenced by the steric environment surrounding the carbonyl group. Aliphatic aldehydes and simple alkyl halides appear inert under the reaction conditions for either alkylation or the pinacol coupling reaction.
- Zhang, Wen-Chun,Li, Chao-Jun
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p. 3230 - 3236
(2007/10/03)
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- Manganese-mediated carbon-carbon bond formation in aqueous media: Chemoselective allylation and pinacol coupling of aryl aldehydes
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The use of manganese as a mediator for allylations and pinacol couplings in aqueous media was investigated. The combination of manganese and copper is found to be a highly effective mediator for the allylation of aryl aldehydes in water. Such a combination is found to be more reactive than other previously reported metals in aqueous media. No reaction was observed with either manganese or copper alone as the mediator. Only a catalytic amount of copper is required for the proceeding of the reaction. The uses of Cu(0), Cu(I), and Cu(II) as the copper source are all effective. The use of a catalytic amount of manganese combined with a stoichoimetric amount of copper led to the failure of the reaction. Allyl chloride is found to be more effective than allyl bromide for the corresponding reaction. The use of substituted allyl halides gave a mixture of regio- and diastereoisomers. Aromatic aldehydes reacted chemoselectively in the presence of aliphatic aldehydes. An exclusive selectivity was also observed when both an aliphatic and an aromatic aldehyde functionalities are present in the same molecule. In the presence of acetic acid or ammonium chloride, manganese was found to effect the pinacol-coupling reaction in water. The reaction proceeds selectively with aryl aldehydes.
- Li, Chao-Jun,Meng, Yue,Yi, Xiang-Hui,Ma, Jihai,Chan, Tak-Hang
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p. 7498 - 7504
(2007/10/03)
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