- AlCl3 catalyzed coupling of: N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon-nitrogen bond cleavage
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A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.
- Hu, Chen,Hong, Gang,Qian, Xiaofei,Kim, Kwang Rim,Zhu, Xiaoyan,Wang, Limin
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supporting information
p. 4984 - 4991
(2017/07/10)
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- Room Temperature, Reductive Alkylation of Activated Methylene Compounds: Carbon-Carbon Bond Formation Driven by the Rhodium-Catalyzed Water-Gas Shift Reaction
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The rhodium-catalyzed water-gas shift reaction has been demonstrated to drive the reductive alkylation of several classes of activated methylene compounds at room temperature. Under catalysis by rhodium trichloride (2-3 mol %), carbon monoxide (10 bar), water (2-50 equiv), and triethylamine (2.5-7 equiv), the scope has been successfully expanded to cover a wide range of alkylating agents, including aliphatic and aromatic aldehydes, as well as cyclic ketones, in moderate to high yields. This method is comparable to, and for certain aspects, surpasses the established reductive alkylation protocols.
- Denmark, Scott E.,Ibrahim, Malek Y. S.,Ambrosi, Andrea
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p. 613 - 630
(2017/06/05)
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- Development of drug intermediates by using direct organocatalytic multi-component reactions
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Development of drug intermediates by using direct amino acid organocatalytic multi-component reaction was investigated. Hydrogenations of double-bond containing compounds including carbonyls, imines and olefins are important for living organisms as well as for the industrial production of chemicals. Amino acid catalysis has emerged as a powerful green synthetic tool for the development of both achiral and chiral catalysis of condensations and cycloadditions and the 1,2- and 1,4-additions of enals, enones and ketones including electrophiles. It was found that the amino acid proline 4a catalyzes the Knoevenagel condenstion of cyclohexanone 1a with the CH-acid ethyl cyanoacetate 2a to furnish the active olefin 9aa. This simple and environmentally friendly approach can be used to construct highly substituted hydrogenated products in a regioselective fashion with good yields.
- Ramachary, Dhevalapally B.,Kishor,Reddy, G. Babul
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p. 1641 - 1646
(2008/02/03)
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- A remarkable effect of bases on the catalytic radical addition of cyanoacetates to alkenes using a Mn(II)/Co(II)/O2 redox system
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A remarkable addition effect of bases, like AcOK, was observed in the radical addition of cyanoacetates to alkenes catalyzed by a Mn(II)/Co(II)/O 2 redox system. Thus, a carbon radical from ethyl cyanoacetate could be catalytically generated by
- Kagayama, Takashi,Fuke, Takahiro,Sakaguchi, Satoshi,Ishii, Yasutaka
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p. 1673 - 1676
(2007/10/03)
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- CARBON-CARBON BOND FORMATION USING MANGANESE(III) ACETATE AS AN ELECTROCHEMICAL MEDIATOR
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Anodic oxidation in a solution containing a variety of olefins and a small amount of Mn(OAc)2*4H2O brought about Mn+3-mediated carbon-carbon bond formation, such as efficient carboxymethylation of styrene derivatives to the corresponding γ-aryl-γ-butyrolactones, and selective coupling of active methylene compounds with non-activated monoolefins, unconjugated dienes or 5-arylpent-1-enes.
- Shundo, Ryushi,Nishiguchi, Ikuzo,Matsubara, Yoshiharu,Hirashima, Tsuneaki
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p. 831 - 840
(2007/10/02)
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- Selective Coupling of Non-Activated Olefins with Ethyl Cyanoacetate by Mn(3+)-Mediated Anodic Oxidation
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Novel carbon-carbon bond formation of non-activated olefins with ethyl cyanoacetate has been developed by anodic oxidation using only small amount of Mn(OAc)2*4H2O to give selectively either saturated or unsaturated coupling products depending upon the pr
- Shundo, Ryushi,Nishiguchi, Ikuzo,Matsubara, Yoshiharu,Hirashima, Tsuneaki
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p. 2285 - 2288
(2007/10/02)
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- REACTIVITY OF CYCLOALKENES IN THE RADICAL ADDITION REACTION WITH ETHYL CYANOACETATE
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The effect of ring size on the reactivity of C5 to C12 cycloalkenes in the copper(II) oxide catalysed and dibenzoyl peroxide initiated addition reaction with ethyl cyanoacetate was determined at 90 deg C using the method of competition reactions. cis-Cycl
- Hajek, Milan,Malek, Jaroslav
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p. 1940 - 1949
(2007/10/02)
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