- Organophotoredox-Catalyzed Decarboxylative N-Alkylation of Sulfonamides
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We developed an organophotoredox-catalyzed reaction for N-alkylation of sulfonamides with aliphatic carboxylic acid-derived redox active esters as alkylating reagents. Under mild and transition metal-free conditions, a series of functionalized N-alkylated sulfonamides were prepared. This protocol also enabled the functionalization of pharmaceutical drugs bearing a sulfonamide or carboxylic acid moiety. This radical-mediated process allowed the assembly of three components including sulfonamides, redox active esters, and alkenes to yield complex sulfonamides in a one-pot manner.
- Nakagawa, Masanari,Nagao, Kazunori,Ikeda, Zenichi,Reynolds, Matthew,Ibá?ez, Ignacio,Wang, Junsi,Tokunaga, Norihito,Sasaki, Yusuke,Ohmiya, Hirohisa
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p. 3930 - 3933
(2021/08/03)
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- Halogen-Bond-Induced Consecutive Csp3-H Aminations via Hydrogen Atom Transfer Relay Strategy
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The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular Csp3-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.
- Alom, Nur-E,Ariyarathna, Jeewani P.,Bassiouni, Omar H.,Kaur, Navdeep,Kennell, Maureen L.,Li, Wei,Wu, Fan
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p. 2135 - 2140
(2020/04/09)
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- Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides
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The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.
- Marcyk, Paul T.,Jefferies, Latisha R.,AbuSalim, Deyaa I.,Pink, Maren,Baik, Mu-Hyun,Cook, Silas P.
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supporting information
p. 1727 - 1731
(2019/01/21)
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- Intermolecular Radical C(sp3)?H Amination under Iodine Catalysis
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The direct amination of aliphatic C?H bonds has remained one of the most tantalizing transformations in organic chemistry. Herein, we report on a unique catalyst system, which enables the elusive intermolecular C(sp3)?H amination. This practical synthetic strategy provides access to aminated building blocks and fosters innovative multiple C?H amination within a new approach to aminated heterocycles. The synthetic utility is demonstrated by the synthesis of four relevant pharmaceuticals.
- Bosnidou, Alexandra E.,Mu?iz, Kilian
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supporting information
p. 7485 - 7489
(2019/04/30)
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- Structural and energetic aspects of adamantane and memantine derivatives of sulfonamide molecular crystals: Experimental and theoretical characterisation
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A number of new sulfonamide compounds with adamantane and memantine fragments were synthesised and characterised. Their single crystals were grown and crystal structures were determined. XPac analysis has revealed three sets of isostructural crystals based on adamantane/memantine-specific hydrogen bond patterns. The use of QTAIMC and Hirshfeld surface analysis allowed elucidating the influence of functional groups and molecular arrangement on the strength of inter- and intramolecular non-covalent interactions in crystals and overall packing efficiency. It was found that the bulky memantine fragment hinders the formation of C(4) hydrogen-bonded chains, leading to the formation of dimeric structures with lower stabilisation energy. The layered packing of hydrophobic fragments in the group of isostructural crystals was found to be the most effective for a group of adamantane derivatives of P21/c symmetry.
- Voronin, Alexander P.,Volkova, Tatiana V.,Ilyukhin, Andrey B.,Trofimova, Tatiana P.,Perlovich, German L.
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p. 3476 - 3489
(2018/07/03)
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- Organocatalytic nitrenoid transfer: Metal-free selective intermolecular C(sp3)-H amination catalyzed by an iminium salt
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This report details the first organocatalytic method for nitrenoid transfer and its application to intermolecular, site-selective C(sp3)-H amination. The method utilizes a trifluoromethyl iminium salt as the catalyst, iminoiodinanes as the nitrogen source, and substrate as the limiting reagent. Activated, benzylic, and aliphatic substrates can all be selectively functionalized in yields up to 87%. A mechanistic proposal for the observed reactivity supported by experimental evidence invokes the intermediacy of a diaziridinium salt or related organic nitrenoid, species that have not been previously explored for the purpose of C-H amination. Finally, examples of late-stage functionalization of complex molecules highlight the selectivity and potential utility of this catalytic method in synthesis.
- Combee, Logan A.,Raya, Balaram,Wang, Daoyong,Hilinski, Michael K.
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p. 935 - 939
(2018/02/07)
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- Direct Sulfonamidation of Primary and Secondary Benzylic Alcohols Catalyzed by a Boronic Acid/Oxalic Acid System
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The direct sulfonamidation of primary and secondary benzylic alcohols catalyzed by a 2,3,4,5-tetrafluorophenylboronic acid/oxalic acid co-catalytic system was examined. The reaction proceeds under mild conditions with readily available starting materials and has been shown to be gram-scalable without significant decrease of yield. Both primary and secondary benzylic alcohols were evaluated and afforded the desired sulfonamide products with good to excellent yields.
- Verdelet, Tristan,Ward, Robert M.,Hall, Dennis G.
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p. 5729 - 5738
(2017/10/06)
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- Catalytic B(C6F5)3[rad]H2O-promoted defluorinative functionalization of tertiary aliphatic fluorides
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A B(C6F5)3[rad]H2O-catalyzed defluorinative functionalization of tertiary aliphatic fluorides is described that proceeds under benign reaction conditions. The synthetic utility of the method is exemplified throu
- Dryzhakov, Marian,Richmond, Edward,Li, Guang,Moran, Joseph
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- Sulfonamide-Linked ciprofloxacin, sulfadiazine and amantadine derivatives as a novel class of inhibitors of jack bean urease; synthesis, kinetic mechanism and molecular docking
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Sulfonamide derivatives serve as an important building blocks in the drug design discovery and development (4D) process. Ciprofloxacin-, sulfadiazine- and amantadine-based sulfonamides were synthesized as potent inhibitors of jack bean urease and free rad
- Channar, Pervaiz Ali,Saeed, Aamer,Albericio, Fernando,Larik, Fayaz Ali,Abbas, Qamar,Hassan, Mubashir,Raza, Hussain,Seo, Sung-Yum
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- Visible-light-mediated, nitrogen-centered radical amination of tertiary alkyl halides under metal-free conditions to form α-tertiary amines
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A mild and operationally convenient amino-functionalization of a range of tertiary alkyl halides by reaction with iminoiodinanes (PhINNs) and I2 has been developed. According to the mechanistic experiments described within, the reaction is spec
- Brueckner, Alexander C.,Hancock, Erin N.,Anders, Evan J.,Tierney, Matthew M.,Morgan, Heather R.,Scott, Kristina A.,Lamar, Angus A.
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supporting information
p. 4387 - 4392
(2016/06/06)
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- Adamantane derivatives of sulfonamides: Sublimation, solubility, solvation and transfer processes in biologically relevant solvents
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Eight adamantane derivatives of sulfonamides were synthesized and characterized. Temperature dependencies of saturation vapor pressure were obtained using the transpiration method and thermodynamic functions of the sublimation processes were calculated. S
- Perlovich,Volkova,Sharapova,Kazachenko,Strakhova,Proshin
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p. 9281 - 9294
(2016/04/09)
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- Adamantane derivatives of sulfonamide molecular crystals: Structure, sublimation thermodynamic characteristics, molecular packing, and hydrogen bond networks
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The crystal structures of six adamantane derivatives of sulfonamides have been determined by X-ray diffraction. The molecular conformational states, packing architecture, and hydrogen bond networks were analyzed. The conformational flexibility of the bridge connecting the phenyl ring and the adamantane fragment was studied. The molecular packing architectures of the selected crystals can be for convenience divided into three different groups. The thermodynamic aspects of the sublimation processes of the compounds were studied by determining the temperature dependence of vapor pressure using the transpiration method. The thermophysical characteristics of the fusion processes of the molecular crystals were measured and analyzed. Correlations between the sublimation thermodynamic functions and physico-chemical descriptors were revealed. A regression equation correlating the sublimation Gibbs energies with the van der Waals molecular volumes was derived. The influence of various molecular fragments on the crystal lattice energy was analyzed. The relationship between the melting points of the studied substances and the free volume per molecule in the crystal lattices was evaluated.
- Perlovich, German L.,Ryzhakov, Alex M.,Tkachev, Valery V.,Proshin, Alexey N.
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p. 753 - 763
(2015/02/19)
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- A versatile tripodal Cu(I) reagent for C-N bond construction via nitrene-transfer chemistry: Catalytic perspectives and mechanistic insights on C-H aminations/amidinations and olefin aziridinations
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A CuI catalyst (1), supported by a framework of strongly basic guanidinato moieties, mediates nitrene-transfer from PhI=NR sources to a wide variety of aliphatic hydrocarbons (C-H amination or amidination in the presence of nitriles) and olefins (aziridination). Product profiles are consistent with a stepwise rather than concerted C-N bond formation. Mechanistic investigations with the aid of Hammett plots, kinetic isotope effects, labeled stereochemical probes, and radical traps and clocks allow us to conclude that carboradical intermediates play a major role and are generated by hydrogen-atom abstraction from substrate C-H bonds or initial nitrene-addition to one of the olefinic carbons. Subsequent processes include solvent-caged radical recombination to afford the major amination and aziridination products but also one-electron oxidation of diffusively free carboradicals to generate amidination products due to carbocation participation. Analyses of metal- and ligand-centered events by variable temperature electrospray mass spectrometry, cyclic voltammetry, and electron paramagnetic resonance spectroscopy, coupled with computational studies, indicate that an active, but still elusive, copper-nitrene (S = 1) intermediate initially abstracts a hydrogen atom from, or adds nitrene to, C-H and C=C bonds, respectively, followed by a spin flip and radical rebound to afford intra- and intermolecular C-N containing products.
- Bagchi, Vivek,Paraskevopoulou, Patrina,Das, Purak,Chi, Lingyu,Wang, Qiuwen,Choudhury, Amitava,Mathieson, Jennifer S.,Cronin, Leroy,Pardue, Daniel B.,Cundari, Thomas R.,Mitrikas, George,Sanakis, Yiannis,Stavropoulos, Pericles
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supporting information
p. 11362 - 11381
(2014/09/17)
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- Nonheme iron-mediated amination of C(sp3)-H bonds. Quinquepyridine-supported iron-imide/nitrene intermediates by experimental studies and DFT calculations
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The 7-coordinate complex [Fe(qpy)(MeCN)2](ClO4) 2 (1, qpy = 2,2′:6′,2″:6″, 2′′′:6′′′,2′′′′- quinquepyridine) is a highly active nonheme iron catalyst for intra- and intermolecular amination of C(sp3)-H bonds. This complex effectively catalyzes the amination of limiting amounts of not only benzylic and allylic C(sp3)-H bonds of hydrocarbons but also the C(sp3)-H bonds of cyclic alkanes and cycloalkane/linear alkane moieties in sulfamate esters, such as those derived from menthane and steroids cholane and androstane, using PhI=NR or "PhI(OAc)2 + H2NR" [R = Ts (p-toluenesulfonyl), Ns (p-nitrobenzenesulfonyl)] as nitrogen source, with the amination products isolated in up to 93% yield. Iron imide/nitrene intermediates [Fe(qpy)(NR)(X)]n+ (CX, X = NR, solvent, or anion) are proposed in these amination reactions on the basis of experimental studies including ESI-MS analysis, crossover experiments, Hammett plots, and correlation with C-H bond dissociation energies and with support by DFT calculations. Species consistent with the formulations of [Fe(qpy)(NTs)2] 2+ (CNTs) and [Fe(qpy)(NTs)]2+ (C) were detected by high-resolution ESI-MS analysis of the reaction mixture of 1 with PhI=NTs (4 equiv). DFT calculations revealed that the reaction barriers for H-atom abstraction of cyclohexane by the ground state of 7-coordinate C NTs and ground state of C are 15.3 and 14.2 kcal/mol, respectively, in line with the observed high activity of 1 in catalyzing the C-H amination of alkanes under mild conditions.
- Liu, Yungen,Guan, Xiangguo,Wong, Ella Lai-Ming,Liu, Peng,Huang, Jie-Sheng,Che, Chi-Ming
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supporting information
p. 7194 - 7204
(2013/06/27)
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- NAlkylation of tosylamides using esters as primary and tertiary alkyl sources: Mediated by hydrosilanes activated by a ruthenium catalyst
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Select your group: Either a primary or tertiary alkyl group can be selectively introduced onto the nitrogen atom of tosylamides in a ruthenium-catalyzed reaction employing hydrosilanes through a judicious choice in the esters that serve as the alkyl source (see scheme; Ts= 4-toluenesulfonyl). These N-alkylation reactions are useful for construction of naturally occurring azacyclic skeletons. Copyright
- Nishikata, Takashi,Nagashima, Hideo
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supporting information; experimental part
p. 5363 - 5366
(2012/07/03)
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- O-alkoxyphenyliminoiodanes: Highly efficient reagents for the catalytic aziridination of alkenes and the metal-free amination of organic substrates
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Efficient nitrene precursors: Highly reactive iminoiodane-based nitrene precursors were prepared from ortho-alkoxyiodobenzenes. Owing to the presence of the ortho-substituent on the phenyl ring, these new iminoiodanes have excellent solubility in organic
- Yoshimura, Akira,Nemykin, Victor N.,Zhdankin, Viktor V.
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supporting information; experimental part
p. 10538 - 10541
(2011/11/12)
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- Iodine-catalyzed aminosulfonation of hydrocarbons by imidoiodinanes. a synthetic and mechanistic investigation
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The amino-functionalization of a range of benzylic and some aliphatic saturated and unsaturated hydrocarbons by reaction with imido-iodinanes (PhI=NSO2Ar) is catalyzed by I2 under operationally simple and mild conditions. The first examples of 1,2-functionalization of unactivated C-H bonds using imido-iodinanes as aminating agents are reported. Mechanistic investigations, including Hammett analysis, kinetic isotope effects, a cyclopropane clock experiment, and stereoselectivity tests, are indicative of a stepwise pathway in C-N bond formation. Investigation into the nature of the active aminating species has led to the isolation of a novel aminating agent formulated as (ArSO2N)xIy (x = 1, y = 2; or x = 3, y = 4).
- Lamar, Angus A.,Nicholas, Kenneth M.
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supporting information; experimental part
p. 7644 - 7650
(2010/12/25)
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- Hydrous zinc halide-catalyzed aminosulfonation of hydrocarbons
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Benzylic and allylic hydrocarbons are selectively converted to the corresponding sulfonamides by a ZnBr2-H2O-catalyzed reaction with PhI=NTs; saturated adamantane is aminosulfonated at the tertiary C-H bond. The Royal Society of Chemistry.
- Kalita, Biswajit,Lamar, Angus A.,Nicholas, Kenneth M.
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supporting information; experimental part
p. 4291 - 4293
(2009/03/12)
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- Oxidation chemistry of poly(ethylene glycol)-supported carbonylruthenium(ii) and dioxoruthenium(vi) meso-tetrakis(pentafluorophenyl) porphyrin
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[Ru11(F20-tpp)(CO)] (1, F20-tpp = meso-tetrakis(pentafluorophenyl)porphyrinato dianion) was covalently attached to poly(ethylene glycol) (PEG) through the reaction of 1 with PEG and sodium hydride in DMF. The water-soluble PEG-supported ruthenium porphyrin (PEG-1) is an efficient catalyst for 2,6-Cl2pyNO oxidation and PhI=NTs aziridination/amidation of hydrocarbons, and intramolecular amidation of sulfamate esters with PhI (OAc)2. Oxidation of PEG-1 by m-CPBA in CH2C12, dioxane, or water afforded a water-soluble PEG-supported dioxoruthenium(VI) porphyrin (PEG-2), which could react with hydrocarbons to give oxidation products in up to 80 % yield. The behavior of the two PEG-supported ruthenium porphyrin complexes in water was probed by NMR spectroscopy and dynamic light-scattering measurements. PEG-2 is remarkably stable to water. The secondorder rate constants (k2) for the oxidation of styrene and ethylbenzene by PEG-2 in dioxane-water increase with water content, and the k2 values at a water content of 70% or 80% are up to 188 times that obtained in ClCH2CH2Cl.
- Zhang, Jun-Long,Huang, Jie-Sheng,Che, Chi-Ming
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p. 3020 - 3031
(2008/02/04)
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- Reactivity of cage-like amines toward p-toluenesulfonyl chloride and diphenyl chlorophosphate in acetonitrile
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The nucleophilic reactivity of amines of the norbornane, norbornene, and adamantane series toward p-toluenesulfonyl chloride and diphenyl chlorophosphate in acetonitrile at 25°C is determined mainly by the steric factor. Parameters characterizing spatial accessibility of the reaction center in the amine molecule have been determined. Cage-like substituents show no appreciable effect on the amine reactivity, as compared to common alkyl groups.
- Sadovskii,Solomoichenko,Kas'yan,Golodaeva,Anikanova,Kas'yan,Savelova
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- Amidation of saturated C-H bonds catalyzed by electron-deficient ruthenium and manganese porphyrins. A highly catalytic nitrogen atom transfer process
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(equation presented) Amidation of a variety of hydrocarbons with PhI=NTs catalyzed by ruthenium and manganese meso-tetrakis(pentafluorophenyl)porphyrins 1 and 2 afforded N-substituted amides in up to 92% yields with good to excellent substrate conversions. By employing catalyst 2, exceptionally high turnovers (up to 2600) were achieved, and the amidations can be effected by directly using PhI(OAc)2/NH2R as amidating reagents; in the case of R = COCF3 a direct amination was realized in up to 90% yield.
- Yu, Xiao-Qi,Huang, Jie-Sheng,Zhou, Xiang-Ge,Che, Chi-Ming
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p. 2233 - 2236
(2007/10/03)
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- Amidation of unfunctionalized hydrocarbons catalyzed by ruthenium cyclic amine or bipyridine complexes
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Selective amidation of simple hydrocarbons with pre-isolated and in-situ formed iminoiodanes catalyzed by ruthenium complexes [Ru(III)(Me3tacn)(CF3CO2)3·H2O] (2b, Me3tacn = N,N',N-trimethyl-1,4,7-triazacyclononane) and cis-[Ru(II)(6,6'-Cl2bpy)2Cl2] (3, 6,6'-Cl2bpy = 6,6'-dichloro-2,2'-bipyridine) was investigated. With PhI=NTs as nitrogen source, both catalysts efficiently promote the amidation of adamantane, cyclohexene, ethylbenzene, cumene, indan, tetralin, and diphenylmethane to afford N-substituted sulfonamides in 80-93% yields with high selectivity. Competitive amidations of para-substituted ethylbenzenes and kinetic isotope effect for the amidation of cyclohexene/cyclohexene-d10 suggest that the amidation processes probably proceed via the hydrogen abstraction by a reactive Ru=NTs species to form a carboradical intermediate. The amidation with PhI(OAc)2/TsNH2 gave results comparable to those obtained with PhI=NTs. Extension of the 'PhI(OAc)2/TsNH2 + catalyst 2b or 3' protocol to MeSO2NH2 and PhCONH2 with ethylbenzene as substrate produced the corresponding N-substituted amides in up to 89% yield.
- Au,Huang,Che,Yu
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p. 7858 - 7864
(2007/10/03)
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- Aziridination of alkenes and amidation of alkanes by bis(tosylimido)ruthenium(VI) porphyrins. A mechanistic study
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Bis(tosylimido)ruthenium(VI) porphyrins, [Ru(VI)(Por)(NTs)2] (Por = TPP, TTP, 4-C1-TPP, 4-MeOTPP, OEP), were prepared in 60-74% yields by treatment of [Ru(II)(Por)(CO)(MeOH)] with (N-(p-tolylsulfonyl)- imino)phenyliodinane (PhI=NTS) in dichloromethane. In dichloromethane containing pyrazole, they reacted with alkenes or alkanes to give tosylamidoruthenium(IV) porphyrins, [Ru(IV)(Por)(NHTs)(pz)], in about 75% yields. The reactions of [Ru(VI)(TPP)(NTs)2] and [Ru(VI)(OEP)(NTs)2] with styrene, para-substituted styrenes, norbornene, cyclooctene, and β- methylstyrene afforded the corresponding N-tosylaziridines in 66-85% yields. The aziridination of cis-stilbene and cis-β-methylstyrene by [Ru(VI)(Por)(NTs)2] is nonstereospecific with a partial loss of the alkene stereochemistry. Kinetic studies on the reactions between [Ru(VI)(TPP)(NTs)2] and 16 alkenes (cyclooctene, norbornene, 2,3-dimethyl-2- butene, styrene, para-substituted styrenes, α and β-methylstyrene, and α- and β-deuteriostyrene) gave the second-order rate constants (k2) ranging from (1.60 ± 0.06) x 10-3 to (90 ± 4) x 10-3 dm3 mo1-1 s-1 at 298 K. The slope of the linear plot of log k2 vs E(l/2) for eight representative alkenes was found to be -1.7 V-1. In the case of para-substituted styrenes, linear correlation between log k(R) (k(R) = relative rate) and σ+ gives a ρ+ value as small as -1.1. However, the effect of para substituents on k(R) can be best accounted for by considering both the polar and spin delocalization effect. Measurements on the secondary deuterium isotope effect revealed that only the β-carbon atom of styrene experienced a significant change in its hybridization in reaching the transition state. All these are consistent with rate-determining formation of a carboradical intermediate. The reactions of [Ru(VI)(TPP)(NTs)2] and [Ru(VI-) (OEP)(NTs)2] with adamantane, cyclohexene, ethylbenzene, and cumene resulted in tosylamidation of these hydrocarbons and afforded the corresponding amides in 52-88% yields. For cyclohexane and toluene, the tosylamidation products were formed in poor yields (ca. 10%). Kinetic studies on the reactions between [Ru(VI-) (TPP)(NTs)2] and nine hydrocarbons (cumene, ethylbenzene, cyclohexene, and para-substituted ethylbenzenes) gave the second-order rate constants (k2) in the range of (0.330 ± 0.008) x 10-3 to (16.5 ± 0.3) x 10-3 dm3 mol-1 s-1. These reactions exhibit a large primary deuterium isotope effect, with a k(H)/k(D) ratio of 11 for the tosylamidation of ethylbenzene. In the case of para-substituted ethylbenzenes, both electron-donating and -withdrawing substituents moderately promote the reaction. There is an excellent linear correlation between log k(R) and a related carboradical parameter. On the basis of these observations, a mechanism involving the rate-limiting formation of a carboradical intermediate is postulated.
- Au, Sze-Man,Huang, Jie-Sheng,Yu, Wing-Yiu,Fung, Wai-Hong,Che, Chi-Ming
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p. 9120 - 9132
(2007/10/03)
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- Ruthenium-mediated amidation of saturated C-H bonds and crystal structure of a bis(tosyl)amidoruthenium(III) complex of 1,4,7-trimethyl-1,4,7-triazacyclononane
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A bis(tosyl)amidoruthenium(III) complex of 1,4,7-trimethyl-1,4,7-triazacyclononane (Me3tacn) is prepared, and its crystal structure revealed the two tosylamido ligands in a cis configuration; the '[Ru(III)(Me3tacn)(NHTs)2(
- Au, Sze-Man,Zhang, Suo-Bo,Fung, Wai-Hong,Yu, Wing-Yiu,Che, Chi-Ming,Cheung, Kung-Kai
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p. 2677 - 2678
(2007/10/03)
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- Functionalisation of Saturated Hydrocarbons. Part 1. Some Reactions of a Ferrous Chloride-Chloramine-T Complex with Hydrocarbons
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The reactions of several hydrocarbons substrates with a ferrous chloride-chloramine-T complex, generated in situ, have been studied.Tosylamination of adamantane and chlorination of mesitylene proceed in good yield while naphthalene gives N,N'-bis(toluene-p-sulphonyl)-1,4-naphthoquinone di-imine.A variety of olefinic substrates undergo both cis- and trans-addition to the double bond as well as allylic functionalisation.
- Barton, Derek H. R.,Hay-Motherwell, Robyn S.,Motherwell, William B.
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p. 445 - 452
(2007/10/02)
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- REACTIONS OF 1.3-DEHYDROADAMANTANE (3.3.1-PROPELLANE SYSTEM) WITH CH- AND NH-ACIDS.
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Reactions of 1.3-dehydroadamantane with aniline in the presence of its hydrochloride, p-toluenesulfamide, and malonic ester are investigated.
- Kogay, B. E.,Sokolenko, W. A.
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p. 613 - 616
(2007/10/02)
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