- Probing the Diastereoselectivity of Staudinger Reactions Catalyzed by N-Heterocyclic Carbenes
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The reaction of ethylphenylketene with 1,3-dimesitylimidazol-2-ylidene (IMes) or 1,3-dimesitylimidazolin-2-ylidene (SIMes) afforded the corresponding azolium enolates in high yields. The two zwitterions were fully characterized by various analytical techn
- Hans, Morgan,Wouters, Johan,Demonceau, Albert,Delaude, Lionel
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Read Online
- Regioselective N-F and α C(sp3)-H Arylation of Aliphatic N-Fluorosulfonamides with Imidazopyridines
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A regioselective arylation of aliphatic N-fluorosulfonamides with imidazopyridines enabled by breaking of N-F and α C(sp3)-H bond to form C-N and C-C bonds was described. With CuCl as the catalyst, a radical mechanism was proposed to produce N-arylated aliphatic sulfonamides via a N radical intermediate. Importantly, under acidic conditions, an in situ generated imine was the possible intermediate, which was trapped by imidazopyridines to form α C(sp3)-H arylated aliphatic sulfonamides. The current protocol featured a broad substrate scope, tunable reaction conditions, operational convenience, and good regioselectivity.
- Xue, Yuting,Shi, Linlin,Wang, Xu,Yu, Xiaoni,Zhu, Xinju,Hao, Xin-Qi,Song, Mao-Ping
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Read Online
- Copper-boryl mediated transfer hydrogenation of N-sulfonyl imines using methanol as the hydrogen donor
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B2Pin2-assisted copper-catalyzed transfer hydrogenation of aromatic sulfonylimines has been achieved, delivering a variety of aryl/heteroaryl sulfonamides in good to excellent yields under mild reaction conditions and with methanol a
- He, Yi,Li, Shi-Guang,Mbaezue, Ifenna I.,Reddy, Angula C.S.,Tsantrizos, Youla S.
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supporting information
(2021/03/24)
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- Decarboxylative Mannich Reactions with Substituted Malonic Acid Half-Oxyesters
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The decarboxylative Mannich reaction between imines and substituted malonic acids half-oxyesters (SMAHOs) has been developed using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst. The reaction proceeds under simple reaction conditions and toler
- Xavier, Tania,Condon, Sylvie,Pichon, Christophe,Le Gall, Erwan,Presset, Marc
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p. 5452 - 5462
(2021/05/07)
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- Synthesis and biological evaluation of substituted phenyl azetidine-2-one sulphonyl derivatives as potential antimicrobial and antiviral agents
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In the present study, we intend to synthesize a series of novel substituted phenyl azetidine-2-one sulphonyl derivatives. The entire set of derivatives 5 (a-t) were screened for in-vitro antibacterial, and antifungal activity, and among them eleven compou
- Mandal, Milan Kumar,Ghosh, Swagatika,Bhat, Hans Raj,Naesens, Lieve,Singh, Udaya Pratap
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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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- Accelerated Reactivity Mechanism and Interpretable Machine Learning Model of N-Sulfonylimines toward Fast Multicomponent Reactions
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We introduce chemical reactivity flowcharts to help chemists interpret reaction outcomes using statistically robust machine learning models trained on a small number of reactions. We developed fast N-sulfonylimine multicomponent reactions for understanding reactivity and to generate training data. Accelerated reactivity mechanisms were investigated using density functional theory. Intuitive chemical features learned by the model accurately predicted heterogeneous reactivity of N-sulfonylimine with different carboxylic acids. Validation of the predictions shows that reaction outcome interpretation is useful for human chemists.
- Jethava, Krupal P.,Fine, Jonathan,Chen, Yingqi,Hossain, Ahad,Chopra, Gaurav
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supporting information
p. 8480 - 8486
(2020/11/18)
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- Methyltrioxorhenium/urea hydrogen peroxide catalyzed oxidation of N-sulfinyl imines: A mild and highly efficient access to N-sulfonyl aldimines, ketimines and α-ketiminoesters
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A mild and highly efficient access to N-sulfonyl imines through the oxidation of corresponding N-tert-butylsulfinyl imines and N-p-tosyl-sulfinyl imines with UHP in the presence of catalytic amount MTO was developed. Under mild reaction conditions, this h
- Tan, Yu,Ma, Ru-Lin,Lin, Hua,Sun, Xing-Wen
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supporting information
(2020/11/25)
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- Ni(0)-Catalyzed Three-Component Coupling Reaction of Tetrafluoroethylene and N-Sulfonyl-Substituted Imines with Silanes via Aza-Nickelacycles
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A nickel-catalyzed three-component coupling reaction of tetrafluoroethylene (TFE) and N-sulfonyl-substituted imines with silanes that furnishes a variety of fluorine-containing amines is disclosed. Stoichiometric experiments revealed that the aza-nickelac
- Shirataki, Hiroshi,Ono, Takafumi,Ohashi, Masato,Ogoshi, Sensuke
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supporting information
p. 851 - 856
(2019/05/16)
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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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- Manganese-Catalyzed N-Alkylation of Sulfonamides Using Alcohols
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An efficient manganese-catalyzed N-alkylation of sulfonamides has been developed. This borrowing hydrogen approach employs a well-defined and bench-stable Mn(I) PNP pincer precatalyst, allowing benzylic and simple primary aliphatic alcohols to be employed as alkylating agents. A diverse range of aryl and alkyl sulfonamides undergoes mono-N-alkylation in excellent isolated yields (32 examples, 85% average yield).
- Reed-Berendt, Benjamin G.,Morrill, Louis C.
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p. 3715 - 3724
(2019/03/30)
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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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- NHC ligand-enabled Ni-catalyzed reductive coupling of alkynes and imines using isopropanol as a reductant
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A nickel-catalyzed reductive coupling of alkynes and imines using readily available isopropanol as the reducing agent was developed. The use of a sterically bulky and electron-rich carbene ligand (AnIPr) significantly promotes the reaction, providing various multi-substituted allylic amines in 23-89% yield and the corresponding chiral ligand (AnIPr-3) can afford the products in 51-95% ee.
- Yao, Wei-Wei,Li, Ran,Li, Jiang-Fei,Sun, Juan,Ye, Mengchun
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supporting information
p. 2240 - 2244
(2019/05/17)
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- Stereoselective synthesis of unnatural (2S, 3S)-6-hydroxy-4-sphingenine-containing sphingolipids
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6-Hydroxy-(4E)-sphingenine-containing sphingolipids are found in mammalian and bacterial membranes and have multiple intra- and intercellular functions. Most sphingolipids contain a (2S,3R)-2-amino-1,3-diol core structure, but only limited examples of unnatural (2S,3S)-2-amino-1,3-diol derivates have so far been reported. Using an underexplored hydrozirconation-transmetalation reaction and an unusual three-step-one-pot deprotection sequence, we were able to synthesize several unnatural (2S,3S)-6-hydroxy-(4E)-sphingenine-containing sphingolipids in only three (protected) or four (deprotected) consecutive steps, respectively, including a fluoresence-labeled derivative suitable for future biological studies.
- Leichnitz, Daniel,Pflanze, Sebastian,Beemelmanns, Christine
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supporting information
p. 6964 - 6969
(2019/08/01)
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- An Assessment of Electrophilic N-Transfer of Oxaziridine with Different 2-, 3-, and 4-Carbon Donor–Acceptor Substrates to Furnish Diverse N-Containing Heterocycles in a Single Step
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An assessment of the scope and limitations of electrophilic N-transfer of oxaziridine in the presence of MgI2 has been carried out with different donor–acceptor carbon substrates. One step access to multifunctional three-, four-, and five-membe
- Ghosh, Asit,Chawla, Vatan,Banerjee, Prabal
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supporting information
p. 3806 - 3814
(2019/06/24)
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- Domino Synthesis of 3-Alkyliden-2,3-Dihydro-4-Quinolones
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The synthesis of 3-alkyliden-2,3-dihydro-4-quinolones has been accomplished in a domino fashion through a three-step sequence that comprised an initial aza-Baylis-Hillman reaction, followed by a 1,3-rearrangement and an intramolecular amination. Starting from readily available aryl vinyl ketones and N-tosyl imines, the reaction with PPh3, CsOAc and CuI in CH3CN gave rise, in good overall yields, to final 3-alkyliden-4-quinolone derivatives, valuable scaffolds in medicinal chemistry. The simultaneous addition of two bases, PPh3 and CsOAc, was found to be crucial for the success of the process. While PPh3 promoted the reversible aza-Baylis-Hillman reaction, CsOAc triggered the subsequent 1,3-rearrangement, which shifted the initial equilibrium and allowed to complete the synthetic sequence upon the addition of CuI. (Figure presented.).
- Raga, Esther,Escolano, Marcos,Torres, Javier,Rabasa-Alca?iz, Fernando,Sánchez-Roselló, María,del Pozo, Carlos
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supporting information
p. 1102 - 1107
(2019/01/30)
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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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- 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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- A General Asymmetric Formal Synthesis of Aza-Baylis–Hillman Type Products under Bifunctional Catalysis
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A new organocatalytic strategy for the synthesis of enantioenriched aza-Baylis–Hillman type products via a frustrated vinylogous reaction is presented. This process proceeds under mild conditions with good yields, completed Z/E selectivity and excellent e
- Frías, María,Carrasco, Ana Cristina,Fraile, Alberto,Alemán, José
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supporting information
p. 3117 - 3121
(2017/12/26)
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- Copper-Catalyzed Silylation of C(sp3)-H Bonds Adjacent to Amide Nitrogen Atoms
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A copper-catalyzed C-Si bond formation between N-halogenated amides and Si-B reagents is described. This oxidative coupling enables the silylation of C(sp3)-H bonds α to an amide nitrogen atom. The utility of the new method is demonstrated for
- Feng, Jian-Jun,Oestreich, Martin
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supporting information
p. 4273 - 4276
(2018/07/29)
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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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- 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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- Fe(III)/ l -Valine-Catalyzed One-Pot Synthesis of N -Sulfinyl- and N -Sulfonylimines via Oxidative Cascade Reaction of Alcohols with Sulfinamides or Sulfonamides
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An efficient Fe(III), l -valine, and 4-OH-TEMPO catalytic system was found for the oxidation of alcohols followed by condensation with sulfinamide or sulfonamide in one pot for the synthesis of N -sulfinyl- and N- sulfonylimines compounds under mild conditions. This transformation accommodates a variety of substrates, shows high functional-group tolerance, and affords the corresponding products in good to excellent yields.
- Zhang, Guofu,Xing, Yunzhe,Xu, Shengjun,Ding, Chengrong,Shan, Shang
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supporting information
p. 1232 - 1238
(2018/03/23)
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- Method for synthesizing 2,3-dihydropyrrole rings
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The invention discloses a method for synthesizing 2,3-dihydropyrrole rings from p-toluenesulfonyl imine and disubstituted allene under the condition of a phosphine catalyst. The method is a convenient route for synthesizing 2,3-dihydropyrrole ring compounds without a metal reagent, and an obtained hydrogenated pyrrole product is a common basic structure in certain bioactive molecules and has potential pharmacochemical study value. The method for synthesizing the 2,3-dihydropyrrole rings adopts mild conditions and simple and available raw materials, and 2-position different substituted 2,3-dihydropyrrole compounds can be prepared conveniently.
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Paragraph 0037; 0038
(2017/10/23)
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- Transition-Metal-Free Trifluoromethylation of Aldehyde Derivatives with Sodium Trifluoromethanesulfinate
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A metal-free and cost-effective synthetic protocol for the trifluoromethylation of N,N-disubstituted hydrazones with Langlois's reagent (CF3SO2Na) to afford the corresponding functionalized trifluoromethyl ketone hydrazones has been established. It is proposed that a radical/SET mechanism proceeding via a trifluoroalkyl radical may be involved in the reaction. Applications of the methodology in industry will be found and the development of new methods for trifluoromethylation with Langlois's reagent will be continued in our laboratory.
- Tan, Zheng,Zhang, Shiwei,Zhang, Yan,Li, Yunpeng,Ni, Minjie,Feng, Bainian
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p. 9384 - 9399
(2017/09/23)
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- Highly Enantioselective Ferrocenyl Palladacycle-Acetate Catalysed Arylation of Aldimines and Ketimines with Arylboroxines
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Benzylic N-substituted stereocenters constitute a frequent structural motif in drugs. Their highly enantioselective generation is hence of technical importance. An attractive strategy is the arylation of imines with organoboron reagents. Chiral Rh complexes have reached a high level of productivity for this reaction type. In this article we describe that an electron rich PdIIcatalyst also performs well in the arylation of aldimines, comparable to the best Rh catalysts. The ferrocenyl palladacycle-acetate catalyst allows for a broad substrate scope and very high enantioselectivities. Commonly observed side reactions like aryl–aryl homocouplings and imine hydrolysis could be blocked. Mechanistic studies implicate that a) the acetate ligand is crucial for transmetallation, b) the active catalyst is most likely a palladacycle-OAc monomer, c) the rate limiting step is probably the product release. By added KOAc the arylation could also be applied to ketimines.
- Schrapel, Carmen,Frey, Wolfgang,Garnier, Delphine,Peters, René
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supporting information
p. 2448 - 2460
(2017/02/23)
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- Synthesis of Mono-N-sulfonylimidazolidines by a 1,3-Dipolar Cycloaddition Strategy, as an Alternative to Selective N-Sulfonylation, and Their Ring Cleavage To Afford 1,2-Diamines
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1,3-Dipolar cycloaddition between nonstabilized azomethine ylides and N-sulfonylimines has been developed, providing practical access to mono-N-sulfonylimidazolidines. The enhanced reactivity of N-sulfonylimines as dipolarophiles towards azomethine ylides
- Laha, Joydev K.,Jethava, Krupal P.,Tummalapalli, K. S. Satyanarayana,Sharma, Sheetal
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p. 4617 - 4624
(2017/08/30)
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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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- Developments in the Reactivity of 2-Methylimidazolium Salts
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Unexpected and unusual reactivity of 2-methylimidazolium salts toward aryl-N-sulfonylimines and aryl aldehydes is here reported. Upon reaction with aryl-N-sulfonylimines, the addition product, arylethyl-2-imidazolium-1-tosylamide (3), is formed with moderate to good yields, while upon reaction with aldehydes, the initial addition product (6) observed in NMR and HPLC-MS experimental analysis is postulated by us as an intermediate to the final conversion to carboxylic acids. Studies in the presence and absence of molecular oxygen allow us to conclude that the imidazolium salts is crucial for the oxidation. A detailed mechanistic study was carried out to provide insights regarding this unexpected reactivity.
- Peixoto, Daniela,Figueiredo, Margarida,Gawande, Manoj B.,Corvo, Marta C.,Vanhoenacker, Gerd,Afonso, Carlos A.M.,Ferreira, Luisa M.,Branco, Paula S.
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p. 6232 - 6241
(2017/06/23)
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- Oxaziridinium compound (by machine translation)
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Various applications such as various reaction using compound [a] oxidant oxaziridines, safe and simple, while eliminating as much as possible intrusion of impurities which can be efficiently manufactured oxaziridinium compound production method. The follo
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- Nickel-catalyzed product-controllable amidation and imidation of sp3 C-H bonds in substituted toluenes with sulfonamides
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A nickel-catalyzed product-controllable imidation and amidation of sp3 C-H bonds in substituted toluenes with sulfonamides were developed. Based on the change of the reaction time and atmosphere from N2 to O2, this reaction proceeded in high yields and excellent selectivity under different conditions. Mechanistic details were also described.
- Li, Ze-lin,Jin, Li-kun,Cai, Chun
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supporting information
p. 1317 - 1320
(2017/02/15)
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- Direct synthesis of N-sulfinyl- and N-sulfonylimines via copper/l-proline-catalyzed aerobic oxidative cascade reaction of alcohols with sulfinamides or sulfonamides
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An efficient one-pot synthetic method of N-sulfinyl- and N-sulfonylimines by the condensation of alcohols with sulfinamides or sulfonamides under mild and green conditions has been developed using a combination of CuI, l-proline and TEMPO. This system shows excellent functional group compatibility for a wide range of substrates and affords the corresponding products in good to excellent yields.
- Zhang, Guofu,Xu, Shengjun,Xie, Xiaoqiang,Ding, Chengrong,Shan, Shang
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p. 9431 - 9435
(2017/02/15)
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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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- Direct Mannich-Type Reactions Promoted by Frustrated Lewis Acid/Br?nsted Base Catalysts
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Direct Mannich-type reactions that afford both α- and β-amino esters by the reaction of a broad range of carbonyl compounds and aldimines are disclosed. The transformation is promoted by a sterically frustrated Lewis acid/Br?nsted base pair, which is prop
- Chan, Jessica Z.,Yao, Wenzhi,Hastings, Brian T.,Lok, Charles K.,Wasa, Masayuki
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supporting information
p. 13877 - 13881
(2016/10/26)
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- Rh-Catalyzed, Regioselective, C-H Bond Functionalization: Access to Quinoline-Branched Amines and Dimers
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Rh-catalyzed, chelation-induced, C-5 regioselective C-H functionalization of 8-amidoquinolines with a range of N-Boc aminals is reported for the first time. The addition of in situ generated imines to C(sp2)-H bonds afforded branched amines in
- Reddy, M. Damoder,Fronczek, Frank R.,Watkins, E. Blake
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supporting information
p. 5620 - 5623
(2016/11/17)
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- Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions
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The key factors for carbonyl-stabilised ammonium ylide-mediated epoxidation reactions were systematically investigated by experimental and computational means and the hereby obtained energy profiles provide explanations for the observed experimental results. In addition, we were able to identify the first tertiary amine-based chiral auxiliary that allows for high enantioselectivities and high yields for such epoxidation reactions.
- Novacek, Johanna,Roiser, Lukas,Zielke, Katharina,Robiette, Rapha?l,Waser, Mario
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supporting information
p. 11422 - 11428
(2016/08/03)
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- Copper-Catalyzed Addition of Alkylboranes to Iminoacetates: Access to α-Alkyl Branched α-Amino Acids
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A copper(I)-catalyzed addition of alkylborane reagents to α-iminoacetates has been developed to assemble both acyclic and cyclic α-branched α-amino carboxylic acid derivatives in good yields. A wide variety of unactivated alkenes are well tolerated in this transformation. (Figure presented.).
- Xiao, Xinsheng,Zhang, Wei,Lu, Xiaoxia,Deng, Yuanfu,Jiang, Huangfeng,Zeng, Wei
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p. 2497 - 2509
(2016/08/16)
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- Triiodide-Mediated δ-Amination of Secondary C?H Bonds
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The Cδ?H amination of unactivated, secondary C?H bonds to form a broad range of functionalized pyrrolidines has been developed by a triiodide (I3?)-mediated strategy. By in situ 1) oxidation of sodium iodide and 2) sequestration of the transiently generated iodine (I2) as I3?, this approach precludes undesired I2-mediated decomposition which can otherwise limit synthetic utility to only weak C(sp3)?H bonds. The mechanism of this triiodide-mediated cyclization of unbiased, secondary C(sp3)?H bonds, by either thermal or photolytic initiation, is supported by NMR and UV/Vis data, as well as intercepted intermediates.
- Wappes, Ethan A.,Fosu, Stacy C.,Chopko, Trevor C.,Nagib, David A.
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supporting information
p. 9974 - 9978
(2016/08/16)
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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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- Metal-Free Amidation of Ethers with N, N -Dibromosulfonamides
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A new metal-free amidation of ethers with N,N-dibromosulfonamides has been developed. A series of hemiaminal ethers or imines were prepared with moderate to good yields.
- Wang, Yuan-Yuan,Sun, Ming-Hui,Zeng, Ning-Ning,Chen, Jie,Zhou, Ling
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supporting information
p. 1438 - 1442
(2016/06/01)
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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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p. 2716 - 2718
(2016/06/15)
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- An efficient synthesis of dihydrobenzo[c]azepines from Morita-Baylis-Hillman adducts via Pictet-Spengler reaction
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Various dihydrobenzo[c]azepines were synthesized in good yields via Pictet-Spengler cyclization protocol from tosylamide derivatives of Morita-Baylis-Hillman adducts and 1,3,5-trioxane. The synthesis was carried out in the presence of easily removable mon
- Moon, Hye Ran,Kim, Su Yeon,Roh, Hwa Jung,Kim, Jae Nyoung
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p. 680 - 684
(2016/05/19)
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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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- Nitroxyl-Radical-Catalyzed Oxidative Coupling of Amides with Silylated Nucleophiles through N-Halogenation
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A nitroxyl-radical-catalyzed oxidative coupling reaction between amines with an N-protecting electron-withdrawing group (EWG) and silylated nucleophiles was developed to furnish coupling products in high yields, thus opening up new frontiers in organocatalyzed reactions. This reaction proceeded through the activation of N-halogenated amides by a nitroxyl-radical catalyst, followed by carbon–carbon coupling with silylated nucleophiles. Studies of the reaction mechanism indicated that the nitroxyl radical activates N-halogenated amides, which are generated from N-EWG-protected amides and a halogenation reagent, to give the corresponding imines.
- Moriyama, Katsuhiko,Kuramochi, Masako,Fujii, Kozo,Morita, Tsuyoshi,Togo, Hideo
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supporting information
p. 14546 - 14551
(2016/11/23)
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- Carbocations as Lewis acid catalysts: Reactivity and scope
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One class of potential Lewis acids that has received negligible attention as a catalyst is the carbocation. Here we show the potential of triarylmethylium ions as highly powerful Lewis acid catalysts for organic reactions. The Lewis acidity of the triarylmethylium ion can be easily tuned by variation of the electronic properties of the aromatic rings and the catalytic activity of the carbocation is shown to correlate directly to the level of stabilization of the empty pC-orbital at the cationic carbon. The versatility of triarylmethylium ions as efficient Lewis acid catalysts for organic reactions is demonstrated in Diels-Alder, aza-Diels-Alder, conjugate addition, halogenation, epoxide rearrangement and intramolecular hetro-ene reactions.
- Bah, Juho,Naidu, Veluru Ramesh,Teske, Johannes,Franzn, Johan
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supporting information
p. 148 - 158
(2015/01/30)
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- Dynamic Covalent Organocatalysts Discovered from Catalytic Systems through Rapid Deconvolution Screening
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The first example of a bifunctional organocatalyst assembled through dynamic covalent chemistry (DCC) is described. The catalyst is based on reversible imine chemistry and can catalyze the Morita-Baylis-Hillman (MBH) reaction of enones with aldehydes or N-tosyl imines. Furthermore, these dynamic catalysts were shown to be optimizable through a systemic screening approach, in which large mixtures of catalyst structures were generated, and the optimal catalyst could be directly identified by using dynamic deconvolution. This strategy allowed one-pot synthesis and in situ evaluation of several potential catalysts without the need to separate, characterize, and purify each individual structure. The systems were furthermore shown to catalyze and re-equilibrate their own formation through a previously unknown thiourea-catalyzed transimination process.
- Schaufelberger, Fredrik,Ramstr?m, Olof
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supporting information
p. 12735 - 12740
(2015/09/01)
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- Exogenous-Base-Free Palladacycle-Catalyzed Highly Enantioselective Arylation of Imines with Arylboroxines
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Enantiomerically pure benzylic amines are important for the development of new drugs. A readily accessible planar-chiral ferrocene-derived palladacycle is shown to be a highly efficient catalyst for the formation of N-substituted benzylic stereocenters; t
- Schrapel, Carmen,Peters, Ren
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supporting information
p. 10289 - 10293
(2015/09/01)
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- Diastereoselective Johnson-Corey-Chaykovsky trifluoroethylidenation
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(2,2,2-Trifluoroethyl)diphenylsulfonium triflate was found to be an efficient ylide reagent for the Johnson-Corey-Chaykovsky reaction to afford trifluoromethyl epoxides, cyclopropanes and aziridines. Interestingly, excellent but different diastereoselectivity was observed for these transformations. Both trifluoromethyl epoxides and cyclopropanes were obtained with trans-selectivity, whereas aziridines were obtained with cis-selectivity.
- Duan, Yaya,Zhou, Bin,Lin, Jin-Hong,Xiao, Ji-Chang
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supporting information
p. 13127 - 13130
(2015/08/18)
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- Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction
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A simple and efficient synthetic route to substituted N-sulfinyl and N-sulfonyl azetidines is described involving imino-aldol reaction of ester enolates with racemic and non-racemic aldimines for obtaining β-amino esters as a key step. These β-amino ester
- Ghorai, Manas K.,Das, Subhomoy,Das, Kalpataru,Kumar, Amit
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p. 9042 - 9049
(2015/09/01)
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- Octahedra-based molecular sieve aluminoborate (PKU-1) as solid acid for heterogeneously catalyzed Strecker reaction
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An aluminoborate (PKU-1) with octahedron-based framework was found to be a highly efficient solid acid catalyst for the rapid and convenient synthesis of α-aminonitriles from imines and TMSCN under mild reaction conditions. The catalytic active sites are
- Wang, Weilu,Wang, Ying,Wu, Bin,Cong, Rihong,Gao, Wenliang,Qin, Bo,Yang, Tao
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supporting information
p. 174 - 178
(2015/02/19)
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- Gold-catalyzed cycloisomerization and diels-alder reaction of 1,4,9-dienyne esters to 3 a,6-methanoisoindole esters with pro-inflammatory cytokine antagonist activity
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A synthetic method to prepare 3a,6-methanoisoindole esters efficiently by gold(I)-catalyzed tandem 1,2-acyloxy migration/Nazarov cyclization followed by Diels-Alder reaction of 1,4,9-dienyne esters is described. We also report the ability of one example t
- Susanti, Dewi,Liu, Li-Juan,Rao, Weidong,Lin, Sheng,Ma, Dik-Lung,Leung, Chung-Hang,Chan, Philip Wai Hong
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supporting information
p. 9111 - 9118
(2015/06/16)
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