- Palladium-Catalyzed Regioselective and Stereospecific Ring-Opening Suzuki-Miyaura Arylative Cross-Coupling of 2-Arylazetidines with Arylboronic Acids
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We have developed a palladium-catalyzed regioselective and enantiospecific ring-opening Suzuki–Miyaura arylative cross-coupling of N-tosyl-2-arylazetidines to give enantioenriched 3,3-diarylpropylamines. This reaction represents an example of transition-metal-catalyzed ring-opening cross-coupling using azetidines as a non-classical alkyl electrophile. Density functional theory rationalized the mechanism of the full catalytic cycle, which consists of the selectivity-determining ring opening of the azetidine, reaction with water, rate-determining transmetalation, and reductive elimination. Transition states of the selectivity-determining ring-opening step were systematically determined by the multi-component artificial force induced reaction (MC-AFIR) method to explain the regioselectivity of the reaction. (Figure presented.).
- Takeda, Youhei,Toyoda, Kazuya,Sameera,Tohnai, Norimitsu,Minakata, Satoshi
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supporting information
p. 2796 - 2805
(2021/04/15)
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- Facile synthesis, antimicrobial and antiviral evaluation of novel substituted phenyl 1,3-thiazolidin-4-one sulfonyl derivatives
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A series of novel substituted phenyl 1, 3-thiazolidin-4-one sulfonyl derivatives 5 (a-t) were synthesized and screened for their in-vitro anti-microbial and anti-viral activity. The result of the anti-microbial assay demonstrated compounds 5d, 5f, 5g, 5h,
- Mandal, Milan Kumar,Ghosh, Swagatika,Naesens, Lieve,Bhat, Hans Raj,Singh, Udaya Pratap
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- Chiral-Directing-Group-Assisted Rhodium(III)-Catalyzed Asymmetric Addition of Inert Arene C?H Bond to Aldimines with Subsequent Intramolecular Cyclization
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By using a chiral directing group, an asymmetric rhodium(III)-catalyzed C?H bond addition to aldimines followed by intramolecular cyclization to form chiral isoindolinones has been achieved (up to 68 % yield, up to 93 % ee). A three-component variant that resembles Mannich reaction was also realized (41 % yield, 83 % ee). Product elaborations and preliminary mechanistic studies were described.
- Cai, Xuhong,Chen, Wenkun,Nie, Ruifang,Wang, Jun
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supporting information
p. 16611 - 16615
(2021/10/19)
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- Alkenyl Exchange of Allylamines via Nickel(0)-Catalyzed C-C Bond Cleavage
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A functional group exchange reaction between allylamines and alkenes via nickel-catalyzed C - C bond cleavage and formation was developed. This reaction provides a novel protocol, which does not require the use of unstable imine substrates, for the synthesis of allylamines, which are widely used in the production of fine chemicals, pharmaceuticals, and agrochemicals.
- Fan, Chao,Lv, Xin-Yang,Xiao, Li-Jun,Xie, Jian-Hua,Zhou, Qi-Lin
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supporting information
p. 2889 - 2893
(2019/02/19)
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- Visible-light, iodine-promoted formation of n-sulfonyl imines and n-alkylsulfonamides from aldehydes and hypervalent iodine reagents
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Alternative synthetic methodology for the direct installation of sulfonamide functionality is a highly desirable goal within the domain of drug discovery and development. The formation of synthetically valuable N-sulfonyl imines from a range of aldehydes,
- Hopkins, Megan D,Brandeburg, Zachary C.,Hanson, Andrew J.,Lamar, Angus A
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- A Gold Carbene Manifold to Prepare Fused γ-Lactams by Oxidative Cyclisation of Ynamides
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Gold-catalysed oxidative cyclisation reactions of ynamides offer great promise in γ-lactam synthesis but are limited by preferential over-oxidation to form α-keto imides. Evaluating the factors that might limit N-cyclisation pathways led to effective gold-catalysed conditions that allow access to different fused γ-lactams on changing the ynamide N-substituent and accommodate previously incompatible substitution patterns. New and efficient methods for the synthesis of functionalised 3-aryl indoles and cyclohepta[c]pyrrol-1-one derivatives are presented. These conditions illustrate the complementarity of gold catalysis to other metals.
- Sánchez-Cantalejo, Fernando,Priest, Joshua D.,Davies, Paul W.
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supporting information
p. 17215 - 17219
(2018/11/10)
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- Visible-Light-Mediated Decarboxylative Benzylation of Imines with Arylacetic Acids
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A straightforward method for the visible-light-mediated decarboxylative benzylation of imines is reported. The key feature of this method is the use of simple primary, secondary, and tertiary arylacetic acids as precursors of benzyl radicals, enabling the facile benzylation of a variety of imines under mild conditions. A variety of structurally diverse β-arylethylamines (37 examples) was accessed using this method.
- Guo, Jing,Wu, Qiao-Lei,Xie, Ying,Weng, Jiang,Lu, Gui
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p. 12559 - 12567
(2018/10/20)
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- Nickel(0)-Catalyzed Hydroalkenylation of Imines with Styrene and Its Derivatives
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A nickel(0)-catalyzed hydroalkenylation of imines with styrene and its derivatives is described. A wide range of aromatic and aliphatic imines directly coupled with styrene and its derivatives, thus providing various synthetically useful allylic amines with up to 95 % yield. The reaction offers a new atom- and step-economical approach to allylic amines by using alkenes instead of alkenyl-metallic reagents. Experiments and DFT calculations showed that TsNH2 promotes the proton transfer from the coordinated olefin to the imine, accompanied by a new C?C bond formation.
- Xiao, Li-Jun,Zhao, Chao-Yue,Cheng, Lei,Feng, Bo-Ya,Feng, Wei-Min,Xie, Jian-Hua,Xu, Xiu-Fang,Zhou, Qi-Lin
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supporting information
p. 3396 - 3400
(2018/03/01)
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- Formation of: N -sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes
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A mild and operationally convenient formation of synthetically valuable N-sulfonyl imines from a range of aryl aldehydes by reaction with iminoiodinanes (PhINZ) and I2 has been developed. According to mechanistic experiments described within, the reaction is speculated to proceed through an unconventional light-promoted, N-centered radical (NCR) pathway involving a N,N-diiodosulfonamide reactive species. This method not only provides a new pathway toward the production of activated imines, but also serves as an example of a non-traditional means of carbonyl activation via an NCR species.
- Hopkins, Megan D.,Scott, Kristina A.,Demier, Brettany C.,Morgan, Heather R.,Macgruder, Jesse A.,Lamar, Angus A.
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p. 9209 - 9216
(2017/11/14)
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- Metal-catalyzed formal amidation of alkenes under CO-free condition
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An effective procedure for synthesis of amides from alkenes and [Formula presented] via Pd and Fe catalysts under mild conditions is described. A series of benzamides containing various functional groups can be obtained in reasonable yield and the possible reaction pathway is proposed in this Letter.
- Zhang, Yuanyuan,Ye, Wenjing,Leng, Xue,He, Ying,Zhang, Hui,Xiao, Xiao
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supporting information
p. 4203 - 4206
(2016/08/24)
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- Synthesis of N-Sulfonyl Arylaldimines Developed by Retesting an Old Process
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By simply heating the mixture of an arylaldehyde and a sulfonylisocyanate in a solvent or in neat form under catalyst- and additive-free conditions, the desired N-sulfonylimine was produced with the release of carbon dioxide. The method is characterized b
- Huang, Dayun,Wang, Xuesong,Wang, Xingyong,Chen, Wenwen,Wang, Xinyan,Hu, Yuefei
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supporting information
p. 604 - 607
(2016/02/18)
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- Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles
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Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium nanoparticles has been developed. The reaction proceeded in aqueous media without significant decomposition of the imines by hydrolysis to afford chiral (diarylmethyl)amines in high yields with outstanding enantioselectivities. This catalyst system exhibited the highest turnover number (700) in heterogeneous catalysts reported to date for these reactions. The reusability of the catalyst was also demonstrated.
- Yasukawa, Tomohiro,Kuremoto, Tatsuya,Miyamura, Hiroyuki,Kobayashi, Sh?
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supporting information
p. 2716 - 2718
(2016/06/15)
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- Aza-Morita-Baylis-Hillman reactions catalyzed by a cyclopropenylidene
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Catalysis using a bis(dialkylamino)cyclopropenylidene (BAC) has been developed, which relies on a formal umpolung activation of Michael acceptor pro-nucleophiles. Various aza-Morita-Baylis-Hillman reactions between aromatic, heteroaromatic, or aliphatic imines and acyclic or cyclic α,β-unsaturated ketones and carboxylic acid derivatives have been catalyzed by a BAC under mild conditions. Functionalities such as unprotected amino and hydroxy groups have been tolerated. The catalyst loading was decreased to 1 mol% without loss of activity. The BAC catalyst was shown to be substantially more active than a cyclic (alkyl)(amino) carbene (CAAC), N-heterocyclic carbenes (NHCs), and P- or N-centered Lewis bases.
- Lu, Xun,Schneider, Uwe
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supporting information
p. 12980 - 12983
(2016/11/09)
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- Catalyst-controlled regiodivergent vinylogous aza-Morita–Baylis–Hillman reactions
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Regiodivergent vinylogous aza-Morita–Baylis–Hillman reactions of 3-vinylcyclopent-2-en-1-one 1 were developed in a catalyst-controlled manner. While treatment of 1 with N-tosylarylaldimines 2 in the presence of DABCO gave the α-adducts as the sole regiois
- Hyakutake, Ryuichi,Gondo, Naruhiro,Ueda, Yoshihiro,Yoshimura, Tomoyuki,Furuta, Takumi,Kawabata, Takeo
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supporting information
p. 1321 - 1324
(2018/03/29)
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- Assembly of homoallylamine derivatives through iron-catalyzed three-component sulfonamidoallylation reaction
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An efficient FeCl3-catalyzed three-component reaction between aldehydes, sulfonamides and allylsilanes has been achieved, which provides a convenient, atom-economic and green way to construct homoallylamine derivatives. In addition, this reaction exhibits excellent syn stereoselectivity with γ-substituted allylsilanes. A practical three-component cascade process to homoallylamine derivatives is reported, which uses cheap and environmentally benign FeCl3 as catalyst and shows excellent syn stereoselectivity with γ-substituted allylsilanes.
- Fan, Xiaohui,Zhu, Hong-Bo,Lv, Hao,Guo, Kun,Guan, Yong-Hong,Cui, Xiao-Meng,An, Bin,Pu, Yan-Ling
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p. 588 - 592
(2015/09/01)
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- Dehydrogenation and oxidative coupling of alcohol and amines catalyzed by organosilicon-supported TiO2@PMHSIPN
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The catalytic dehydrogenation and tandem transformation of aromatic alcohols, including oxidative coupling of alcohols and amines, were achieved successfully using a catalytic amount of organosilicon-supported titania (TiO2@PMHSIPN), which enables the efficient synthesis of aromatic aldehydes, imines, and benzimidazoles in good to excellent yields. This journal is the Partner Organisations 2014.
- Wang, Hu,Zhang, Jin,Cui, Yu-Ming,Yang, Ke-Fang,Zheng, Zhan-Jiang,Xu, Li-Wen
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p. 34681 - 34686
(2014/11/08)
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- Iron-catalyzed efficient intermolecular amination of C(sp3)-H bonds with bromamine-T as nitrene source
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[Fe(N4Py)(CH3CN)](ClO4)2 can efficiently catalyze intermolecular nitrene insertion of sp3 C-H bonds with bromamine-T as the nitrene source, forming the desired tosylprotected amines with NaBr as the by-product.
- Wang, Haiyu,Li, Yuxi,Wang, Zhiming,Lou, Jun,Xiao, Yuling,Qiu, Guofu,Hu, Xianming,Altenbach, Hans-Josef,Liu, Peng
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p. 25287 - 25290
(2014/07/07)
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- Enantioselective continuous-flow production of 3-indolylmethanamines mediated by an immobilized phosphoric acid catalyst
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A polystyrene-supported 1,1'-bi-2-naphthol derived phosphoric acid has been synthesized and applied in the enantioselective Friedel-Crafts reaction of indoles and sulfonylimines. The immobilized catalyst was highly active and selective, and gave rise to a
- Osorio-Planes, Laura,Rodriguez-Escrich, Carles,Pericas, Miquel A.
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supporting information
p. 2367 - 2372
(2014/03/21)
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- Rhodium-catalyzed direct addition of indoles to N-sulfonylaldimines
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The rhodium-catalyzed addition of indole C-H bonds to a range of aryl- and alkyl-N-sulfonylaldimines is reported. The reaction proceeds with high functional group compatibility and provides easy and rapid access to a wide variety of 2-indolylmethanamine derivatives under mild reaction conditions.
- Zhou, Bing,Yang, Yaxi,Lin, Sui,Li, Yuanchao
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supporting information
p. 360 - 364
(2013/05/08)
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- Highly enantioselective rhodium-catalyzed [2+2+2] cycloaddition of diynes to sulfonimines
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A new asymmetric [2+2+2] cycloaddition of diynes to sulfonimines under rhodium catalysis that provides the corresponding enantioenriched 1,2-dihydropyridines in good yields is described.
- Amatore, Muriel,Lebuf, David,Malacria, Max,Gandon, Vincent,Aubert, Corinne
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supporting information
p. 4576 - 4579
(2013/05/22)
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- TDAE strategy for the synthesis of 2,3-diaryl N-tosylaziridines
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We report herein an original and rapid synthesis of 2,3-diaryl N-tosylaziridines by TDAE strategy starting from ortho- or para- nitro(dichloromethyl)benzene derivatives and N-tosylimines. A mixture of cis/trans isomers was isolated from 1-(dichloromethyl)-4- nitrobenzene, whereas only trans-aziridines were obtained from ortho-nitro derivatives.
- Khoumeri, Omar,Spitz, Cedric,Terme, Thierry,Vanelle, Patrice
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p. 7364 - 7375
(2013/08/23)
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- One-pot preparation of homopropargylic N-sulfonylamines catalyzed by zinc powder
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A new one-pot method for synthesis of homopropargylic N-sulfonylamines from aldehydes catalyzed by zinc powder is described. The procedure is lauded by its simplicity, good yields, and adaptability to a wide variety of aldehydes.
- Wu, Chao,Huang, Wangyong,He, Weimin,Xiang, Jiannan
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supporting information
p. 1233 - 1234
(2013/10/22)
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- Rh(III)-catalyzed olefination of N-sulfonyl imines: Synthesis of ortho -olefinated benzaldehydes
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Rh(III)-catalyzed olefination of N-sulfonyl imines using acrylates and styrenes has been achieved for the synthesis of ortho-olefinated benaldehydes. This reaction proceeds via a chelation assisted C-H olefination/in situ hydrolysis process.
- Zhang, Tao,Wu, Lamei,Li, Xingwei
-
supporting information
p. 6294 - 6297
(2014/01/17)
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- Chiral diphosphane- and NHC-containing ruthenium catalysts for the catalytic asymmetric arylation of aldimines with organoboron reagents
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For the first time, we report the application of [RuCl2(η 6-p-cymene)]2 in the arylation of N-activated aldimines with boronic acids and its derivatives to afford chiral amines, which are important intermediates in the syntheses of key bioactive compounds. The behavior of the chiral ligands, the imine substrates, and the organoboron reagents were studied. Very good enantioselectivities were obtained. A new method is presented for the synthesis of chiral substituted amines by employing Ru catalysts along with known chiral phosphane ligands and a new NHC-type chiral ligand. Organoboron reagents were applied as the aryl transfer agents. High enantioselectivities were achieved with this new method, and some mechanistic insights are provided.
- Marques, Carolina S.,Burke, Anthony J.
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supporting information; experimental part
p. 4232 - 4239
(2012/09/22)
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- Rh-catalyzed C-C cleavage of benzyl/allylic alcohols to produce benzyl/allylic amines or other alcohols by nucleophilic addition of intermediate rhodacycles to aldehydes and imines
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We report three transformations: 1) direct transformation from biarylmethanols into biarylmethylamines; 2) direct transformation from one biarylmethanol into another biarylmethanol; 3) direct transformation from allylic alcohols into allylic amines. These transformations are based on pyridyl-directed Rh-catalyzed C-C bond cleavage of secondary alcohols and subsequent addition to C=X (X=N or O) double bonds. The reaction conditions are simple and no additive is required. The driving force of C-C bond cleavage is the formation of the stable rhodacycle intermediate. Other directing groups, such as the pyrazolyl group, can also be used although it is not as efficient as the pyridyl group. We carried out in-depth investigations for transformation 1 and found that: 1) the substrate scope was broad and electron-rich alcohols and electron-deficient imines are more efficient; 2) as the leaving group, aldehyde had no significant impact on either the C-C bond cleavage or the whole transformation; 3) mechanistic studies (intermediate isolation, in situ NMR spectroscopic studies, competing reactions, isotopic labeling experiments) implied that: i) The C-C cleavage was very efficient under these conditions; ii) there is an equilibrium between the rhodacycle intermediate and the protonated byproduct phenylpyridine; iii) the addition step of the rhodacycle intermediate to imines was slower than the C-C cleavage and the equilibrium between the rhodacycle and phenylpyridine; iv) the whole transformation was a combination of two sequences of C-C cleavage/nucleophilic addition and C-C cleavage/protonation/C-H activation/nucleophilic addition, with the latter being perhaps the main pathway. We also demonstrated the first example of cleavage of an C(alkenyl)-C(benzyl) bond. These transformations showed the exchange (or substitution) of the alcohol group with either an amine or another alcohol group. Like the "group transplant", this method offers a new concept that can be used to directly synthesize the desired products from other chemicals through reorganization of carbon skeletons.
- Zhang, Xi-Sha,Li, Yang,Li, Hu,Chen, Kang,Lei, Zhi-Quan,Shi, Zhang-Jie
-
supporting information
p. 16214 - 16225
(2013/02/21)
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- α-Aryl-substituted allenamides in an imino-nazarov cyclization cascade catalyzed by Au(I)
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An imino-Nazarov cyclization using α-aryl-substituted allenamides is described. This gold(I)-catalyzed cascade is efficient and regioselective in constructing a diverse array of synthetically useful aromatic-ring fused cyclopentenamides. The success in this transformation represents a solution to the challenge in establishing an imino-Nazarov cyclization process.
- Ma, Zhi-Xiong,He, Shuzhong,Song, Wangze,Hsung, Richard P.
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supporting information
p. 5736 - 5739
(2013/01/15)
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- Ruthenium- and sulfonamide-catalyzed cyclization between N-sulfonyl imines and alkynes
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Ruthenium(II)-catalyzed redox-neutral annulative coupling of N-sulfonyl imines with alkynes has been achieved for the synthesis of indenamines, where a sulfonamide cocatalyst is necessary.
- Zhao, Peng,Wang, Fen,Han, Keli,Li, Xingwei
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supporting information
p. 5506 - 5509,4
(2020/10/15)
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- Synthesis of 2-amino-1,3-dienes by chromium-catalyzed addition of silylated propargyl bromides to imines
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(Silyl)methylallenic amines were synthesized by the chromium-catalyzed addition of (4-bromobutynyl)trimethylsilane to tosyl imines. Regioisomeric mixtures of the desired allene and the corresponding alkyne were obtained. Allenic imines were then treated w
- Durán-Galván, María,Connell, Brian T.
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experimental part
p. 7901 - 7908
(2011/11/07)
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- Asymmetric addition of diethylzinc to aldehydes catalyzed by new zinc-amides prepared by a rhodium-catalyzed asymmetric addition
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A new chiral zinc-amide 2s' was found to be an effective catalyst for the asymmetric addition of diethylzinc to aldehydes 3 through a screening method for asymmetric catalysts, in which two catalytic asymmetric reactions are connected. The chiral zinc cat
- Yoshida, Kazuhiro,Akashi, Naohisa,Yanagisawa, Akira
-
experimental part
p. 1225 - 1230
(2011/10/19)
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- Asymmetric aza-friedel-crafts reaction of 2-naphthol with tosylimines catalyzed by a dinuclear zinc complex
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The first asymmetric aza-Friedel-Crafts reaction of 2-naphthol with tosylimines was developed via a dinuclear zinc catalyst (up to 98% ee). It provided a new method for the asymmetric synthesis of Betti base derivatives.
- Niu, Liang-Feng,Xin, Yang-Chun,Wang, Ren-Lin,Jiang, Fan,Xu, Peng-Fei,Hui, Xin-Ping
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supporting information; experimental part
p. 765 - 768
(2010/06/14)
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- [4+2] Cycloaddition of o-xylylenes with imines using palladium catalyst
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(Chemical Equation Presented) The cycloaddition of o-(silylmethyl)benzylic carbonates with imines proceeded in the presence of the Pd(η3- C3H5)Cp-DPPPent catalyst, affording the tetrahydroisoquinolines in good to high yiel
- Ueno, Satoshi,Ohtsubo, Masakazu,Kuwano, Ryoichi
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supporting information; experimental part
p. 12904 - 12905
(2009/12/05)
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- Base and copper(i) catalyzed Mannich, alkyne hydroamination cascades for the direct synthesis of 2-methylenepyrrolidines
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An efficient, simple-to-perform, one-pot reaction cascade to 2-methylenepyrrolidines from p-toluenesulfonyl protected imines and propargylated malonates under a combination of base and copper(i) catalysis is reported.
- Wang, Hai-Fei,Yang, Ting,Xu, Peng-Fei,Dixon, Darren J.
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supporting information; experimental part
p. 3916 - 3918
(2010/01/06)
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- Preparation of N-arylsulfonyl imines from sulfonamides and aryl aldehydes using magnesium oxide as a heterogeneous and reusable catalyst under solvent-free conditions
-
An efficient solvent-free procedure for the preparation of N-arylsulfonyl imines from sulfonamides and aryl aldehydes in the presence of a catalytic amount of magnesium oxide and tetrabutylammonium bromide (TBAB) under microwave irradiation is described. The advantages of this method are good to high yields, short reaction times, low cost, and matching with green chemistry protocols. Copyright Taylor & Francis Group, LLC.
- Hasaninejad, Alireza,Zare, Abdolkarim,Zare, Ahmad Reza Moosavi,Parhami, Abolfath,Sharghi, Hashem,Khalafi-Nezhad, Ali
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experimental part
p. 2769 - 2776
(2009/09/06)
-
- NK1 ANTAGONIST
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The invention is to a compound exhibiting neurokinin inhibitory properties, a pharmaceutical composition comprising same and a method of treatment for neurokinin-meditated conditions.Formula (I)
- -
-
Page/Page column 39
(2010/02/09)
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- Chemistry of Oxaziridines. 1. Synthesis and Structure of 2-Arenesulfonyl-3-aryloxaziridines. A New Class of Oxaziridines
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A new class of oxaziridine derivatives, 2-arenesulfonyl-3-aryloxaziridines (2), is prepared by m-CPBA oxidation of sulfonimines (RSO2N=CHAr).These compounds are the first stable examples of this ring system to have a substituent other than carbon attached to nitrogen and are characterized by a highly electrophilic oxaziridine oxygen atom.These oxaziridines have the E configuration as determined by X-ray crystallography.The presence of the powerful electron-attracting sulfonyl group attached to nitrogen apparently has little effect on the structure of the oxaziridine three-membered ring.Of more significance are the observations that the nitrogen lone pair in 2 is opposite to one of the sulfonyl oxygens and that the long S-N bond length implies little if any conjugative interaction between sulfur and nitrogen.Attempts to prepare oxaziridines via oxidation of sulfonimines, 5, derived from acetophenone gave imidoyl ether 14, a novel Baeyer-Villiger oxidation product of a C-N double bond.
- Davis, Franklin A.,Lamendola, Joseph,Nadir, Upender,Kluger, Edward W.,Sedergran, Thomas C.,et al.
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p. 2000 - 2005
(2007/10/02)
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