- Copper-boryl mediated transfer hydrogenation of N-sulfonyl imines using methanol as the hydrogen donor
-
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.
-
supporting information
(2021/03/24)
-
- Palladium-Catalyzed Regioselective and Stereospecific Ring-Opening Suzuki-Miyaura Arylative Cross-Coupling of 2-Arylazetidines with Arylboronic Acids
-
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)
-
- Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
-
We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
- Delost, Michael D.,Njardarson, Jon T.
-
supporting information
p. 6121 - 6125
(2021/08/16)
-
- The diastereoselective synthesis of 2,3-diaryl-3-cyano-substituted pyrrolidines via the MgI2 mediated ring expansion of aryl cyclopropyl nitriles
-
The MgI2 mediated reaction of aryl substituted cyclopropyl nitriles with tosyl aldimines to give 2,3-diaryl-3-cyano-substituted pyrrolidines has been demonstrated. In all cases, the trans-diastereoisomer was determined to be the major product.
- Stead, Darren
-
supporting information
(2020/09/04)
-
- Domino Synthesis of 3-Alkyliden-2,3-Dihydro-4-Quinolones
-
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
-
supporting information
p. 1102 - 1107
(2019/01/30)
-
- Practical N-hydroxyphthalimide-mediated oxidation of sulfonamides to N-sulfonylimines
-
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
-
-
- Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze the preparation of N-sulfonylimines
-
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)
-
- Silica-supported zinc chloride (ZnCl2/SiO2)-induced efficient protocol for the synthesis of N-sulfonyl imines and 2-Arylbenzothiazole
-
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)
-
- 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
-
supporting information
p. 2240 - 2244
(2019/05/17)
-
- 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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- 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)
-
- 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)
-
- Synthesis of novel N-(p-toluenesulfonyl)aminophosphonates and evaluation of their biological properties
-
The synthesis of a series of N-sulfonylaminophosphonates 2aA-2dC and evaluation of their cytotoxicity and ecotoxicity is described. N-sulfonylaminophsophonates 2aA-2dC were obtained by addition of dialkyl phosphites to azomethine bonds of sulfonimines 1a-
- Karpowicz, Rafa?,Lewkowski, Jaros?aw,Stasiak, Ma?gorzata,Czopor, Aleksandra,Tokarz, Paulina,Król, Adrianna,Rogacz, Diana,Rychter, Piotr
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p. 423 - 436
(2018/02/06)
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- Visible-light, iodine-promoted formation of n-sulfonyl imines and n-alkylsulfonamides from aldehydes and hypervalent iodine reagents
-
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
-
-
- Branched Amine Synthesis via Aziridine or Azetidine Opening with Organotrifluoroborates by Cooperative Br?nsted/Lewis Acid Catalysis: An Acid-Dependent Divergent Mechanism
-
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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- Verkade's Superbase as an Organocatalyst for the Strecker Reaction
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Proazaphosphatranes -Verkade's superbases- proved to be efficient organocatalysts for the Strecker reaction between protected imines and trimethylsilyl cyanide (TMSCN). Excellent to quantitative yields were reached and, compared to other systems, only low
- Yang, Jian,Chatelet, Bastien,Ziarelli, Fabio,Dufaud, Véronique,Hérault, Damien,Martinez, Alexandre
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supporting information
p. 6328 - 6332
(2018/11/23)
-
- 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
-
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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- Formation of: N -sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes
-
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)
-
- 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)
-
- 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
-
supporting information
p. 2034 - 2037
(2017/05/04)
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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
-
supporting information
p. 4203 - 4206
(2016/08/24)
-
- Synthesis of N-Sulfonyl Arylaldimines Developed by Retesting an Old Process
-
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
-
supporting information
p. 604 - 607
(2016/02/18)
-
- 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.
-
supporting information
p. 9974 - 9978
(2016/08/16)
-
- 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
-
supporting information
p. 502 - 507
(2016/02/18)
-
- 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)
-
- Aza-Morita-Baylis-Hillman reactions catalyzed by a cyclopropenylidene
-
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
-
supporting information
p. 12980 - 12983
(2016/11/09)
-
- 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
-
supporting information
p. 1321 - 1324
(2018/03/29)
-
- A General Method for Imine Formation Using B(OCH2CF3)3
-
Tris(2,2,2-trifluoroethyl)borate [B(OCH2CF3)3] was found to be a mild and general reagent for the formation of a variety of imines by condensation of amides or amines with carbonyl compounds. N-Sulfinyl, N-toluenesulfonyl,
- Reeves, Jonathan T.,Visco, Michael D.,Marsini, Maurice A.,Grinberg, Nelu,Busacca, Carl A.,Mattson, Anita E.,Senanayake, Chris H.
-
supporting information
p. 2442 - 2445
(2015/05/27)
-
- Exogenous-Base-Free Palladacycle-Catalyzed Highly Enantioselective Arylation of Imines with Arylboroxines
-
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
-
supporting information
p. 10289 - 10293
(2015/09/01)
-
- Diastereoselective Johnson-Corey-Chaykovsky trifluoroethylidenation
-
(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
-
supporting information
p. 13127 - 13130
(2015/08/18)
-
- Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction
-
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)
-
- Chemoselective Boron-Catalyzed Nucleophilic Activation of Carboxylic Acids for Mannich-Type Reactions
-
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
-
supporting information
p. 7075 - 7078
(2015/06/25)
-
- Assembly of homoallylamine derivatives through iron-catalyzed three-component sulfonamidoallylation reaction
-
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)
-
- 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
-
p. 7583 - 7593
(2016/01/25)
-
- A general aminocatalytic method for the synthesis of aldimines
-
A general and efficient biomimetic method for the synthesis of aldimines from aldehydes and compounds bearing the NH2 group in the presence of pyrrolidine as a catalyst has been developed. These organocatalytic reactions, based on the application of the concept of nucleophilic catalysis, proceed with outstanding yields in the absence of acids and metals under simple conditions and minimum experimental manipulation. The method has been mainly applied to the synthesis of N-sulfinyl and N-sulfonyl imines, but its general validity has been proven with the preparation of representative N-phosphinoyl, N-alkyl, and N-aryl imines. These unprecedented reactions, which presumably occur via iminium activation without requiring acidic conditions, are an interesting and competitive alternative to the classical methods for preparing aldimines.
- Morales, Sara,Guijarro, Fernando G.,Garcia Ruano, Jose Luis,Cid, M. Belen
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supporting information
p. 1082 - 1089
(2014/02/14)
-
- A Mannich/cyclization cascade process for the asymmetric synthesis of spirocyclic thioimidazolidineoxindoles
-
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
-
supporting information
p. 14771 - 14774
(2015/01/09)
-
- New synthesis of unsymmetrically-substituted 2,5-diarylpyrroles from homopropargyl sulfonamides
-
Unsymmetrically-substituted 2,5-diarylpyrroles were prepared by 5-endo-dig cyclization with consecutive deprotection of homopropargyl sulfonamides. Stepwise elaboration of an aldehyde allows the introduction of a variety of functional aryl moieties at the
- Van Rossom, Wim,Matsushita, Yoshitaka,Ariga, Katsuhiko,Hill, Jonathan P.
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p. 4897 - 4900
(2014/01/23)
-
- Synthesis of di-, tri-, and tetrasubstituted pyridines from (phenylthio)carboxylic acids and 2-[aryl(tosylimino)methyl]acrylates
-
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.
-
supporting information
p. 6496 - 6499
(2015/02/05)
-
- Enantioselective continuous-flow production of 3-indolylmethanamines mediated by an immobilized phosphoric acid catalyst
-
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.
-
supporting information
p. 2367 - 2372
(2014/03/21)
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- A multicomponent approach to the synthesis of N-sulfonyl β2,3-amino esters
-
The multicomponent synthesis of α,β-disubstituted N-sulfonyl β-amino esters is described. It involves a zinc-mediated, cobalt-catalyzed three-component reaction between sulfonylimines, acrylates and organic bromides. A possible mechanism is proposed, emph
- Gall, Erwan Le,Sengmany, Stephane,Samb, Issa,Benakrour, Sabrina,Colin, Christopher,Pignon, Antoine,Leonel, Eric
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supporting information
p. 3423 - 3426
(2014/05/20)
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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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- Asymmetric cyanation of a-ketiminophosphonates catalyzed by cinchona alkaloids: Enantioselective synthesis of tetrasubstituted a-aminophosphonic acid derivatives from trisubstituted a-aminophosphonates
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An enantioselective synthesis of tetrasubstituted a-phosphono-a-amino nitriles through asymmetric cyanation of a-ketiminophosphonates catalyzed by Cinchona alkaloids is reported. a-Ket- ACHTUNGTRENUNGiminophosphonates are generated, in a very efficient sy
- Vicario, Javier,Ezpeleta, Jose Mari,Palacios, Francisco
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supporting information
p. 2641 - 2647
(2013/01/15)
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