- Copper(II) triflate-catalyzed and tosyl isocyanate-mediated three-step tandem synthesis of 9-arylfluorenes
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A Cu(OTf)2-catalyzed and TsNCO-mediated three-step tandem synthesis of 9-arylfluorenes were developed from biphenyls and aryl aldehydes, by which the electron-poor 9-aryl substituted fluorenes were synthesized smoothly. Its success is mainly at
- Huang, Dayun,Wang, Xuesong,Wang, Xingyong,Zhang, Jianlan,Wang, Xinyan,Hu, Yuefei
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Read Online
- Synthesis of Diversely Substituted Imidazolidines via [3+2] Cycloaddition of 1,3,5-Triazinanes with Donor-Acceptor Aziridines and Their Anti-Tumor Activity
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A Y(OTf)3-catalyzed [3+2] cycloaddition of 1,3,5-triazinanes with donor-acceptor aziridines has been developed, accessing diversely substituted imidazolidines high efficiency. Mechanistic investigations support the formation of imidazolidines through an SN1-like pathway. Furthermore, these imidazolidines exhibit promising anti-tumor activity against a series of human cancer cell lines. (Figure presented.).
- Shi, Zhichao,Fan, Tingting,Zhang, Xun,Zhan, Feng,Wang, Zhe,Zhao, Lei,Lin, Jin-Shun,Jiang, Yuyang
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supporting information
p. 2619 - 2624
(2021/04/05)
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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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- Reductive alkylation of imines via asymmetric Cu-catalyzed addition of organozirconium reagents
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Chiral amines are important as medicines or agrochemicals. They are often assembled by nucleophilic addition to corresponding compounds featuring C[dbnd]N bond. Pre-made organometallics are typical nucleophiles in this reaction. In this work, we describe
- Némethová, Ivana,Vargová, Denisa,Mudráková, Brigita,Filo, Juraj,?ebesta, Radovan
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supporting information
(2020/01/08)
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- Pyridinyl Amide Ion Pairs as Lewis Base Organocatalysts
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Pyridinyl amide ion pairs carrying various electron-withdrawing substituents were synthesized with selected ammonium or phosphonium counterions. Compared to neutral pyridine-based organocatalysts, these new ion pair Lewis bases display superior catalytic
- Amp?ler, Torsten,Helberg, Julian,Zipse, Hendrik
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p. 5390 - 5402
(2020/05/19)
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- TfOH-catalyzed formal [3+2] cycloaddition of N-tosylaziridine dicarboxylates and nitriles: Synthesis of tetrafunctionalized 2-imidazolines
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We developed an efficient method for synthesis of tetrafunctionalized 2-imidazolines using TfOH-catalyzed formal [3+2] cycloaddition of N-tosylaziridine dicarboxylates and nitriles. This is the first report of C–N bond cleavage of N-tosylaziridine dicarboxylates catalyzed by Br?nsted acid and the reaction worked well over wide scope of substrates in good to excellent yields under mild conditions. The method has the potential to be applied to pharmaceutical design and synthesis of tetrafunctionalized 2-imidazolines.
- Zuo, Qinglu,Shi, Zhichao,Zhan, Feng,Wang, Zhe,Lin, Jin-Shun,Jiang, Yuyang
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supporting information
(2020/01/13)
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- Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze the preparation of N-sulfonylimines
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A new magnetic nanocatalyzed synthetic method for the synthesis of aldimines was evidenced. The reaction was carried out in a Schlenk tube under reflux conditions using various solvents and different nanomaterials as catalysts. In these reactions, an exce
- Ashouri, Akram,Samadi, Saadi,Nasiri, Behzad,Bahrami, Zohre
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p. 549 - 556
(2019/08/01)
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- Silica-supported zinc chloride (ZnCl2/SiO2)-induced efficient protocol for the synthesis of N-sulfonyl imines and 2-Arylbenzothiazole
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A straightforward strategy for the synthesis of N-sulfonyl imine derivatives from sulfonamides and aryl aldehydes utilizing Silica-supported zinc chloride (ZnCl2/SiO2, silzic) as a catalyst under solvent-free conditions has been developed. 2-Arylbenzothiazole derivatives were also synthesized by the reaction of 2-aminothiophenol with aryl aldehydes under the same conditions. This procedure has advantages of high yields, mild reaction condition, simple procedure, low cost, and simplicity of workup. The catalyst has the same efficiency on its reuse up to three times.
- Soliman, Hanan A.,El-Shahat, Mahmoud,Soliman, Abdel-Ghany
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p. 584 - 591
(2019/07/31)
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- Photoredox Radical/Polar Crossover Enables Construction of Saturated Nitrogen Heterocycles
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Photoredox-mediated radical/polar crossover (RPC) processes offer new avenues for the synthesis of cyclic molecules. This process has been realized for the construction of medium-sized saturated nitrogen heterocycles. Photocatalytically generated alkyl ra
- Pantaine, Lo?c R.E.,Milligan, John A.,Matsui, Jennifer K.,Kelly, Christopher B.,Molander, Gary A.
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supporting information
p. 2317 - 2321
(2019/03/26)
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- Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids
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An approach for efficient synthesis of C-glycosyl amino acids is described. Different from typical photoredox-catalyzed reactions of imines, the new process follows a pathway in which α-imino esters serve as electrophiles in chemoselective addition reactions with nucleophilic glycosyl radicals. The process is highlighted by the mild nature of the reaction conditions, the highly stereoselectivity attending C-C bond formation, and its applicability to C-glycosylations using both armed and disarmed pentose and hexose derivatives.
- Ji, Peng,Zhang, Yueteng,Wei, Yongyi,Huang, He,Hu, Wenbo,Mariano, Patrick A.,Wang, Wei
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supporting information
p. 3086 - 3092
(2019/05/01)
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- Enantioselective Aza-Reformatsky Reaction with Ketimines
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Here, an enantioselective aza-Reformatsky reaction using acyclic ketimine substrates is presented. Using α-phosphorated ketimines as electrophilic substrates and a simple BINOL-derived ligand, phosphorated analogues of aspartic acid holding chiral tetrasubstituted carbons are efficiently obtained with excellent enantioselectivity through an asymmetric organocatalytic Reformatsky-type reaction. The phosphorated analogues of aspartic acid have been used for the synthesis of phosphorus-containing enantiopure tetrasubstituted β-lactams.
- Maestro, Aitor,Martinez De Marigorta, Edorta,Palacios, Francisco,Vicario, Javier
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supporting information
p. 9473 - 9477
(2019/11/28)
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- Practical N-hydroxyphthalimide-mediated oxidation of sulfonamides to N-sulfonylimines
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A new method to prepare sulfonylimines through the oxidation of sulfonamides mediated by N-hydroxyphthalimide under mild conditions has been developed. Compared to reported oxidation methods, broader substrates scope and milder conditions were achieved in
- Wang, Jian,Yi, Wen-Jing
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- Rh(III)-Catalyzed [3 + 2] Annulation via C-H Activation: Direct Access to Trifluoromethyl-Substituted Indenamines and Aminoindanes
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The rhodium(III)-catalyzed direct C-H addition and annulation of benzimidates and aldimines with β-(trifluoromethyl)-α,β-unsaturated ketones is described. This protocol provides the facile and efficient formation of various trifluoromethyl-containing inde
- Chaudhary, Bharatkumar,Auti, Prashant,Shinde, Suchita Dattatray,Yakkala, Prasanna Anjaneyulu,Giri, Deepesh,Sharma, Satyasheel
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supporting information
p. 2763 - 2767
(2019/04/30)
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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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- Branched Amine Synthesis via Aziridine or Azetidine Opening with Organotrifluoroborates by Cooperative Br?nsted/Lewis Acid Catalysis: An Acid-Dependent Divergent Mechanism
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A practical catalytic method to synthesize β,β- and γ,γ-substituted amines by opening aziridines and azetidines, respectively, using alkenyl, alkynyl, or aryl/heteroaryl trifluoroborate salts is described. This reaction features simple open-flask reaction conditions, the use of transition-metal-free catalysis, complete regioselectivity, and high diastereoselectivity. Preliminary mechanistic studies suggest that carbocation formation is disfavored. Stereoretentive addition is favored with Br?nsted acid present, while stereoinversion is favored in its absence, indicating divergent mechanisms.
- Nguyen, Truong N.,May, Jeremy A.
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supporting information
p. 3618 - 3621
(2018/06/26)
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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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- In situ generated cationic Pd(II)/bipyridine-catalyzed addition of arylboronic acids to N-sulfonyl-arylaldimines
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An in situ generated cationic Pd(II)/bipyridine-catalyzed nucleophilic addition of arylboronic acids to N-sulfonyl arylaldimines was developed and optimized, and the reaction was proceeded highly efficiently and conveniently in CH3NO2/sub
- Yang, Zhenyu,Ni, Yuxin,Liu, Rui,Song, Kaixuan,Lin, Shaohui,Pan, Qinmin
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supporting information
p. 2034 - 2037
(2017/05/04)
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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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- Tunable titanocene lewis acid catalysts for selective friedel-crafts reaction of indoles and N-sulfonylaldimines
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A newc strategy to control the selective Friedel-Crafts reaction of indoles and imines under mild conditions was developed. Phenol derivatives were established as efficient ligands to finely tune the activity of titanocene dichloride. Cp2TiCl2 and phenol catalyzed the mono-Friedel-Crafts reaction of indoles and N-sulfonyl aldimines with good yields (91 %), whereas o-aminophenol significantly enhanced the activity of the titanocene catalyst and promoted the synthesis of bisindole with excellent yields (98 %). The new organometallic Lewis acid catalysts are air-tolerant, can be used with low catalyst loading (3 mmol-%) and are compatible with -NO2, -F, -Cl, -Br, and -OMe (30 examples with yields from good to excellent). The titanocene catalysts were fully characterized by NMR and HRMS analysis. The results suggest that Cp2TiCl(OC6H5) (I) and Cp2TiCl(OC6H4NH3+Cl-) (II) were catalytic species for the mono- and double-Friedel-Crafts reactions, respectively. Distinguished from single functional acid catalysts I, catalyst II showed a catalytic cooperative effect of two acid components, which led to a fine tuning of the reactivity as well as to the selectivity of the desired reaction pathways. A Ti-catalyzed, highly selective Friedel-Crafts reaction of indoles and imines has been developed. Cp2TiCl2 and phenol, with a single Lewis acid site, catalyzed the mono-Friedel-Crafts reaction of indoles and N-sulfonylaldimines, whereas o-aminophenol enhanced the acidity of titancene catalyst, enabling both Lewis and Bronsted acid sites to promote the synthesis of bisindole.
- Xiu, Wang,Zhenhua, Wang,Zhang, Guofang,Zhang, Weiqiang,Wu, Ya,Gao, Ziwei
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supporting information
p. 502 - 507
(2016/02/18)
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- Enantioselective Synthesis of α-Amino Phosphonates via Pd-Catalyzed Asymmetric Hydrogenation
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A highly enantioselective palladium-catalyzed hydrogenation of a series of linear and cyclic α-iminophosphonates has been achieved, providing efficient access to optically active α-aminophosphonates with up to 99% ee. (Chemical Equation Presented).
- Yan, Zhong,Wu, Bo,Gao, Xiang,Chen, Mu-Wang,Zhou, Yong-Gui
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supporting information
p. 692 - 695
(2016/03/01)
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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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- Hydrogen peroxide/dimethyl carbonate: A green system for epoxidation of: N -alkylimines and N -sulfonylimines. One-pot synthesis of N -alkyloxaziridines from N -alkylamines and (hetero)aromatic aldehydes
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A green method for epoxidation of imines using an environmentally benign oxidant system, H2O2/dimethyl carbonate, was developed. N-Alkyloxaziridines were prepared in high yields from N-alkylamines and (hetero)aromatic aldehydes in one-pot fashion, whereas N-sulfonyloxaziridines have been prepared by using the same oxidant system and 5 mol% of Zn(OAc)2·2H2O as catalyst.
- Kra?em, Jamil,Ghedira, Donia,Ollevier, Thierry
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supporting information
p. 4859 - 4864
(2016/10/12)
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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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- 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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- Chemoselective Boron-Catalyzed Nucleophilic Activation of Carboxylic Acids for Mannich-Type Reactions
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The carboxyl group (COOH) is an omnipresent functional group in organic molecules, and its direct catalytic activation represents an attractive synthetic method. Herein, we describe the first example of a direct catalytic nucleophilic activation of carbox
- Morita, Yuya,Yamamoto, Tomohiro,Nagai, Hideoki,Shimizu, Yohei,Kanai, Motomu
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supporting information
p. 7075 - 7078
(2015/06/25)
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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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- Selective Synthesis of Tripyrranes, Tetrapyrranes, and Corroles
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A new, catalytic, and general methodology was developed for the direct synthesis of unsymmetrical AB-type tripyrranes by reaction of dipyrromethanesulfonamides with pyrrole. Key structure dipyrromethanesulfonamides were synthesized by the addition of meso
- Aydin, Gokcen,Temelli, Baris,Unaleroglu, Canan
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p. 7583 - 7593
(2016/01/25)
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- A Mannich/cyclization cascade process for the asymmetric synthesis of spirocyclic thioimidazolidineoxindoles
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An asymmetric cascade Mannich/cyclization reaction between 3-isothiocyanato oxindoles and sulfimides using a commercially available organocatalyst has been developed. A wide range of structurally diverse spiro[imidazolidine-4,3′-oxindole] derivatives were
- Cai, Hao,Zhou, Yu,Zhang, Dong,Xu, Jinyi,Liu, Hong
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supporting information
p. 14771 - 14774
(2015/01/09)
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- Synthesis of di-, tri-, and tetrasubstituted pyridines from (phenylthio)carboxylic acids and 2-[aryl(tosylimino)methyl]acrylates
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An isothiourea-catalyzed Michael addition-lactamization followed by the sulfide oxidation-elimination/N- to O-sulfonyl transfer sequence for the formation of 2,3,5- and 2,3-substituted pyridine 6-tosylates from (phenylthio)acetic acids and α,β-unsaturated
- Stark, Daniel G.,O'Riordan, Timothy J. C.,Smith, Andrew D.
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supporting information
p. 6496 - 6499
(2015/02/05)
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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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- 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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- An organocatalytic synthesis of N-sulfonyl imines using chloramine-T in aqueous medium
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N-Sulfonyl imines have been synthesized in good to excellent yields from aldehydes and chloramine-T using proline as an organocatalyst in aqueous medium at ambient temperature. The protocol is applicable to a wide range of aldehydes, especially enals exhi
- Chawla, Ruchi,Singh, Atul K.,Yadav, Lal Dhar S.
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p. 3553 - 3556
(2014/06/10)
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- Heterobimetallic Ir-Sn catalysis: Aza-Friedel-Crafts reaction of N-sulfonyl aldimines
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The heterobimetallic complex [Ir(COD)(SnCl3)Cl(μ-Cl)] 2 catalyzes the aza-Friedel-Crafts reaction of 1,3,5- trimethoxybenzene, as well as substituted indoles with N-sulfonyl aldimines leading to the formation of diarylamines and triarylmethanes in good yields. The symmetrical triarylmethanes were also obtained from diarylamines and suitable nucleophiles via simultaneous cleavage of sp3 C-N bond and elimination of 1,3,5-trimethoxybenzene.
- Chatterjee, Paresh Nath,Maity, Arnab Kumar,Mohapatra, Swapna Sarita,Roy, Sujit
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supporting information
p. 2816 - 2826
(2013/04/10)
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- Diastereoselective synthesis of pyrrolidine derivatives via a one-pot nitro-Mannich/hydroamination cascade using base and gold catalysis
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An efficient one-pot nitro-Mannich/hydroamination cascade reaction for the synthesis of substituted pyrrolidines bearing three stereocentres is reported. Proceeding under the control of a combination of base and gold(i) catalysts, the cascade reaction aff
- ?uri?, Andrej,Barber, David M.,Sanganee, Hitesh J.,Dixon, Darren J.
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supporting information
p. 2777 - 2779
(2013/04/23)
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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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- 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
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supporting information
p. 6294 - 6297
(2014/01/17)
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- Hydrocyanation of sulfonylimines using potassium hexacyanoferrate(II) as an eco-friendly cyanide source
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An efficient and eco-friendly method for hydrocyanation of sulfonylimines via one-pot two-step procedure using potassium hexacyanoferrate(II) as a cyanide source, benzoyl chloride as a promoter, and potassium carbonate as a base is described. This protocol has the features of using nontoxic, nonvolatile and inexpensive cyanide source, high yield, and simple work-up procedure.
- Li, Zheng,Li, Rongzhi,Zheng, Huanhuan,Wen, Fei,Li, Hongbo,Yin, Junjun,Yang, Jingya
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p. 1739 - 1743
(2014/01/06)
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- Synthesis of N-sulfonylimines using CeCl3 under neutral conditions
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An efficient and environmentally benign method for the synthesis of N-sulfonylimines is reported. Condensation of aryl sulfonamides with different aromatic aldehydes and ketones gave N-sulfonylimines in good to excellent yields in the presence of 10 mol% CeCl3 as catalyst. This method can be used with both aldehydes and ketones.
- Zhu, Xun,Wei, Yunyang
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experimental part
p. 363 - 364
(2012/09/22)
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- Rhodium-catalyzed synthesis of branched amines by direct addition of benzamides to imines
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Rhodium-catalyzed addition of benzamide C-H bonds to a range of aromatic N-sulfonyl aldimines has been developed and proceeds with high functional group compatibility. The synthetic utility of the resulting branched amine products has also been demonstrated by the preparation of isoindoline and isoindolinone frameworks.
- Hesp, Kevin D.,Bergman, Robert G.,Ellman, Jonathan A.
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supporting information; experimental part
p. 2304 - 2307
(2012/06/30)
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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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- Organocatalytic trifluoromethylation of imines using phase-transfer catalysis with phenoxides. A general platform for catalytic additions of organosilanes to imines
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A new approach to additions of silicon nucleophiles to imines was developed. The method is based on the phase-transfer of phenoxides by ammonium catalysts, overcoming the inability of amide adducts in promoting the reactions.
- Bernardi, Luca,Indrigo, Eugenio,Pollicino, Salvatore,Ricci, Alfredo
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supporting information; experimental part
p. 1428 - 1430
(2012/03/11)
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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
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supporting information
p. 16214 - 16225
(2013/02/21)
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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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- Amine- and sulfonamide-promoted wittig olefination reactions in water
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Amine-promoted olefination: The reaction of a phosphonium salt and an aldehyde in water to yield alkenes with high E-configurational control is promoted by catalytic amounts of non-basic amines in aqueous bicarbonate media (see scheme). Possible catalytic cycles involving imines and iminium intermediates are discussed.
- McNulty, James,McLeod, David
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supporting information; experimental part
p. 8794 - 8798
(2011/09/14)
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- Lewis acid-catalyzed oxidative allylation: A new approach for the synthesis of homoallylic alcohols and amines directly from alcohols
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A new approach for the synthesis of homoallylic alcohols and amines directly from alcohols via one-pot sequential oxidation-Barbier reaction and oxidation-condensation-Barbier reactions, respectively, is reported. The protocol involves the one-pot ferric chloride-catalyzed oxidation of alcohols to the corresponding aldehydes with chloramine-T followed by indium-mediated Barbier allylation with allyl bromide to afford homoallylic alcohols in 70-90% overall yields. The ferric chloride-catalyzed condensation of aldehydes and oxidation by-product p-toluenesulfonamide followed by indium-mediated Barbier-type allylation of the resulting aldimines with allyl bromide affords homoallylic amines in 60-80% overall yields in the same reaction vessel. The present work demonstrates a new one-pot approach toward homoallylic alcohol and amine synthesis directly from alcohols. Copyright
- Srivastava, Vishnu P.,Patel, Rajesh,Yadav, Lal Dhar S.
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supporting information; experimental part
p. 695 - 700
(2011/05/06)
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