- Conformational study on 2-acyl-1-alkylidene-1,2,3,4-tetrahydroisoquinolines
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The title enamide compounds can exist in either a sickle or U conformation with respect to the C=C-N-C=C conjugated moiety, where the sickle form is greatly favored. The sickle rotamers are chiral in nature in both solution and crystalline states, as prov
- Kitamura, Masato,Tsukamoto, Masaki,Takaya, Hidemasa,Noyori, Ryoji
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- Copper and N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines
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A one-pot two-step oxidative process has been developed for the tert-butyl hydroperoxide mediated transformation of aldehydes and amines into amides catalyzed by copper(I) iodide and an N-heterocyclic carbene. The process is additive-free and does not require the amine to be transformed into its hydrochloride salts. The method is simple and practicable, has a broad substrate scope, and uses economical, feasible, and abundant reagents.
- Singh, Ashmita,Narula, Anudeep Kumar
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supporting information
p. 718 - 722
(2021/02/26)
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- DECONSTRUCTIVE FUNCTIONALIZATION METHODS AND COMPOUNDS
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Disclosed herein, inter alia, are deconstructive functionalization methods and compounds made using the same.
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Paragraph 0435
(2020/01/31)
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- Cross-Dehydrogenating Coupling of Aldehydes with Amines/R-OTBS Ethers by Visible-Light Photoredox Catalysis: Synthesis of Amides, Esters, and Ureas
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A straightforward synthesis of amides, ureas, and esters is reported by visible-light cross-dehydrogenating coupling (CDC) of aldehydes (or amine carbaldehydes) and amines/R-OTBS ethers by photoredox catalysis. The reaction is found to be general and high yielding. A plausible mechanistic pathway has been proposed for these transformations and is supported by appropriate controlled experiments.
- Pandey, Ganesh,Koley, Suvajit,Talukdar, Ranadeep,Sahani, Pramod Kumar
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supporting information
p. 5861 - 5865
(2018/09/21)
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- Ligand-Enabled Enantioselective Csp3 –H Activation of Tetrahydroquinolines and Saturated Aza-Heterocycles by RhI
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The first rhodium(I)-catalyzed enantioselective intermolecular C (Formula presented.) –H activation of various saturated aza-heterocycles including tetrahydroquinolines, piperidines, piperazines, azetidines, pyrrolidines, and azepanes is presented. The combination of a rhodium(I) precatalyst and a chiral monodentate phosphonite ligand is shown to be a powerful catalytic system to access a variety of important enantio-enriched heterocycles from simple starting materials. Notably, the C (Formula presented.) –H activation of tetrahydroquinolines is especially challenging due to the adjacent C (Formula presented.) ?H bond. This redox-neutral methodology provides a new synthetic route to α-N-arylated heterocycles with high chemoselectivity and enantioselectivity up to 97 % ee.
- Gre?ies, Steffen,Klauck, Felix J. R.,Kim, Ju Hyun,Daniliuc, Constantin G.,Glorius, Frank
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supporting information
p. 9950 - 9954
(2018/08/01)
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- Thioamide-Directed Cobalt(III)-Catalyzed Selective Amidation of C(sp3)?H Bonds
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A mild, oxidant-free, and selective Cp*CoIII-catalyzed amidation of thioamides with robust dioxazolone amidating agents via C(sp3)?H bond activation to generate the desired amidated products is reported. The method is efficient and allows for the C?H amidation of a wide range of functionalized thioamides with aryl-, heteroaryl-, and alkyl-substituted dioxazolones under the Cp*CoIII-catalyzed conditions. The observed regioselectivity towards primary C(sp3)?H activation is supported by computational studies and the cyclometalation is proposed to proceed by means of an external carboxylate-assisted concerted metalation/deprotonation mechanism. The reported method is a rare example of the use of a directing group other than the commonly used pyridine and quinolone classes for Cp*CoIII-catalyzed C(sp3)?H functionalization and the first to exploit thioamides.
- Tan, Peng Wen,Mak, Adrian M.,Sullivan, Michael B.,Dixon, Darren J.,Seayad, Jayasree
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supporting information
p. 16550 - 16554
(2017/12/07)
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- Mild and Low-Pressure fac-Ir(ppy)3-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis
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A novel, mild and facile preparation of alkyl amides from unactivated alkyl iodides employing a fac-Ir(ppy)3-catalyzed radical aminocarbonylation protocol has been developed. Using a two-chambered system, alkyl iodides, fac-Ir(ppy)3, amines, reductants, and CO gas (released ex situ from Mo(CO)6), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a wide range of alkyl amides in moderate to excellent yields.
- Chow, Shiao Y.,Stevens, Marc Y.,?kerbladh, Linda,Bergman, Sara,Odell, Luke R.
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supporting information
p. 9155 - 9161
(2016/07/14)
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- Low-Pressure Radical11C-Aminocarbonylation of Alkyl Iodides through Thermal Initiation
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A radical11C-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into11C-labelled amides, including the 11β-HSD1 inhibitor [carbonyl-11C]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated11C-aminocarbonylation, which is limited to the preparation of11C-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon–[11C]CO delivery unit represents a simple and convenient alternative to previous radical11C-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.
- Chow, Shiao Y.,Odell, Luke R.,Eriksson, Jonas
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p. 5980 - 5989
(2016/12/26)
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- Mild and selective Et2Zn-catalyzed reduction of tertiary amides under Hydrosilylation conditions
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Diethylzinc (Et2Zn) can be used as an efficient and chemoselective catalyst for the reduction of tertiary amides under mild reaction conditions employing cost-effective polymeric silane (PMHS) as the hydride source. Crucial for the catalytic activity was the addition of a substoichiometric amount of lithium chloride to the reaction mixture. A series of amides containing different additional functional groups were reduced to their corresponding amines, and the products were isolated in good-to-excellent yields.
- Kovalenko, Oleksandr O.,Volkov, Alexey,Adolfsson, Hans
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supporting information
p. 446 - 449
(2015/03/05)
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- α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp3)-H Coupling
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Pd(II)-catalyzed α-C(sp3)-H arylation of pyrrolidines, piperidines, azepanes, and N-methylamines with arylboronic acids has been developed for the first time. This transformation is applicable to wide arrays of pyrrolidines and boronic acids, including heteroaromatic boronic acids. A diastereoselective one-pot heterodiarylation of pyrrolidines has also been achieved.
- Spangler, Jillian E.,Kobayashi, Yoshihisa,Verma, Pritha,Wang, Dong-Hui,Yu, Jin-Quan
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supporting information
p. 11876 - 11879
(2015/10/05)
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- Cesium carbonate-catalyzed reduction of amides with hydrosilanes
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Cesium carbonate has been found to be an effective catalyst for the reduction of tertiary carboxamides with the simple, commercially available PhSiH3 under solvent-free conditions. The catalytic system can effectively reduce a range of amides under relatively mild conditions (from room temperature to 80 C) to yield the corresponding amines in good to excellent yields (71-100%) and thus has the potential for practical applications.
- Xie, Weilong,Zhao, Mengdi,Cui, Chunming
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p. 7440 - 7444
(2014/04/03)
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- Indium-mediated mild and facile method for the synthesis of amides
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Indium-mediated coupling reactions of acyl chlorides and amines for the synthesis of amide bonds are described. The reaction afforded high yields of the desired amides under mild and neutral conditions, and it was applicable also to the preparation of peptides without epimerization.
- Cho, Dae Hyan,Jang, Doo Ok
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p. 2285 - 2287
(2007/10/03)
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- Eclipsed Conformation of the Exocyclic N-CH2 Bond in N-Neopentylpiperidines and the Stereodynamic Consequences As Studied by Dynamic NMR Spectroscopy and Molecular Mechanics Calculations
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The dynamic stereochemistry of a range of N-neopentylpiperidines 1 with an eclipsed N-CH2-t-Bu bond is compared with that of the corresponding range of N-ethylpiperidines 2 with a gauche N-CH2Me bond. By using dynamic NMR spectroscopy, the relative importance of ring inversion, exocyclic bond rotation, and nitrogen inversion are elucidated and barriers are reported and discussed. Minor populations of the neopentyl-axial-eclipsed conformation are detected directly and identified with the help of molecular mechanics calculations. The corresponding N-alkylpyrrolidines are also reported.
- Anderson, J. Edgar,Ijeh, Anthony I.,Storch, Christine,Casarini, Daniele,Lunazzi, Lodovico
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p. 3310 - 3317
(2007/10/03)
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- Adamantyl-Containing O-Monothioesters. II. Synthesis and Chemical Transformations of O-Methyl (1-Adamantyl)thioacetate in Reaction with Piperidine
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O-Methyl (1-adamantyl)thioacetate has been prepared for the first time by reaction of methyl (1-adamantyl)acetate with phosphorus pentasulfide in dioxane.The reaction of this product with piperidine yields corresponding S-ester, (1-adamantyl)aceto- and (1-adamantyl)thioacetopiperidides, and N-methylpiperidine.A mechanism of this reaction has been proposed, based on comparative analysis of behavior of O-methyl 1-adamantylthioacetate and its analogs, adamantane-1-thiocarboxylic and thiopivalic acid O-esters.
- Klimko, Yu. E.,Isaev, S. D.,Yurchenko, A. G.
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p. 166 - 170
(2007/10/02)
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