- A new preparation of cis-N-sulfonylaziridines from N-sulfonylaldimines using trimethylsilyldiazomethane
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Trimethylsilyldiazomethane smoothly reacts with N-sulfonylaldimines to give 2-substituted N-sulfonyl-3-trimethylsilylaziridines in good yields with high cis selectivity. (C) 2000 Elsevier Science Ltd.
- Hori,Aoyama,Shioiri
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- 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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- 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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- 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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- Catalyst-controlled regiodivergent ring-opening C(sp3)-Si bond-forming reactions of 2-arylaziridines with silylborane enabled by synergistic palladium/copper dual catalysis
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A catalyst-controlled regiodivergent and stereospecific ring-opening C(sp3)-Si cross-coupling of 2-arylaziridines with silylborane enabled by synergistic Pd/Cu dual catalysis has been developed. Just by selecting a suitable combination of catalysts, the regioselectivity of the coupling is completely switched to efficiently provide two regioisomers of β-silylamines (i.e., β-silyl-α-phenethylamines and β-silyl-β-phenethylamines) in good to high yields. Furthermore, a slight modification of the reaction conditions caused a drastic change in reaction pathways, leading to a tandem reaction to produce another regioisomer of silylamine (i.e., α-silyl-β-phenethylamines) in an efficient and selective manner.
- Takeda, Youhei,Shibuta, Kaoru,Aoki, Shohei,Tohnai, Norimitsu,Minakata, Satoshi
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p. 8642 - 8647
(2019/10/02)
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- Asymmetric Stepwise Reductive Amination of Sulfonamides, Sulfamates, and a Phosphinamide by Nickel Catalysis
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Asymmetric reductive amination of poorly nucleophilic sulfonamides was realized in the presence of nickel catalysts and titanium alkoxide. A wide range of ketones, including enolizable ketones and some biaryl ones, were converted into sulfonamides in excellent enantiomeric excess. The cyclization of sulfamates and intermolecular reductive amination of a diarylphosphinamide were also successful. Formic acid was used as a safe and economic surrogate of high-pressure hydrogen gas.
- Zhao, Xiaohu,Xu, Haiyan,Huang, Xiaolei,Zhou, Jianrong Steve
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supporting information
p. 292 - 296
(2018/12/13)
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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)
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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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p. 3396 - 3400
(2018/03/01)
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- Pd/Zn(OTf)2 Co-Catalyzed Asymmetric Hydrogenation of Imines under Normal Pressure of Hydrogen
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An efficient method for the asymmetric hydrogenation of cyclic and acyclic N-sulfonylimines co-catalyzed by Pd/Zn(OTf)2 using hydrogen gas under ambient pressure was developed. The methodology offers an easy access to generate chiral sulfonylam
- Gao, Yang,Yang, Fan,Pu, Dongdong,Laishram, Ronibala Devi,Fan, Ruifeng,Shen, Guoli,Zhang, Xuexin,Chen, Jingchao,Fan, Baomin
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supporting information
p. 6274 - 6279
(2018/11/23)
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- Asymmetric transfer hydrogenation reactions of: N -sulfonylimines by using alcohols as hydrogen sources
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A palladium/zinc co-catalytic system was established and successfully utilized in the asymmetric transfer hydrogenation reactions of N-sulfonylimines with alcohols as hydrogen sources. Simple alcohols such as methanol, ethanol and benzyl alcohols are all
- Yang, Fan,Chen, Jingchao,Shen, Guoli,Zhang, Xuexin,Fan, Baomin
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supporting information
p. 4963 - 4966
(2018/05/23)
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- Copper-Catalyzed Enantioselective Alkylation of Enolizable Ketimines with Organomagnesium Reagents
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Inexpensive and readily available organomagnesium reagents were used for the catalytic enantioselective alkylation of enolizable N-sulfonyl ketimines. The low reactivity and competing enolization of the ketimines was overcome by the use of a copper–phosphine chiral catalyst, which also rendered the transformation highly chemoselective and enantioselective for a broad range of ketimine substrates.
- Ortiz, Pablo,Collados, Juan F.,Jumde, Ravindra P.,Otten, Edwin,Harutyunyan, Syuzanna R.
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supporting information
p. 3041 - 3044
(2017/03/14)
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- Carbene-catalyzed LUMO activation of alkyne esters for access to functional pyridines
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A carbene-catalyzed LUMO activation of α,β-unsaturated alkyne esters is reported. This catalytic process allows for effective reactions of alkyne esters with enamides to synthesize functional pyridines via simple protocols. A previously unexplored unsaturated alkyne acyl azolium intermediate is involved in the key step of the reaction.
- Mou, Chengli,Wu, Jichang,Huang, Zhijian,Sun, Jun,Jin, Zhichao,Chi, Yonggui Robin
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supporting information
p. 13359 - 13362
(2017/12/26)
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- Direct Synthesis of Enolizable N-Sulfonyl Ketimines under Microwave Irradiation
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N-sulfonyl imines are widely used as substrates for a range of transformations. Access to N-sulfonyl aldimines is straightforward through direct condensation between the parent aldehyde and the sulfonamide. However, this approach is not efficient for the
- Ortiz, Pablo,Collados, Juan F.,Harutyunyan, Syuzanna R.
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supporting information
p. 1247 - 1250
(2016/03/19)
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- Solvent-free synthesis of N-sulfonyl imines using WCl6 as a novel, highly efficient and reusable catalyst
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WCl6 was used as a novel, efficient and reusable catalyst for the preparation of N-sulfonyl imines via the condensation of sulfonamides with aldehydes as well as isatin under solvent-free conditions. The turn-over frequency (TOF) value of the c
- Zolfigol, Mohammad Ali,Tavasoli, Mahsa,Moosavi-Zare, Ahmad Reza,Arghavani-Hadi, Parastoo,Zare, Abdolkarim,Khakyzadeh, Vahid
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p. 7692 - 7696
(2013/07/05)
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- Reduction of sulfonylimines with raney nickel
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Raney-Ni/EtOH reduction of different N-sulfonylimines provides a new entry for synthesizing sulfonamides in good yields under mild conditions. This protocol, which does not require additional hydrogen, constitutes a cheap, safe, and easy-to-handle alterna
- Ruano, Jose Luis Garca,Fernandez-Salas, Jose A.,Maestro, M. Carmen,Parra, Alejandro
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p. 198 - 207,10
(2020/09/02)
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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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- Activation of the Si-B Linkage: Copper-Catalyzed addition of nucleophilic silicon to imines
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Activation of the Si-B bond through copper-catalyzed transmetalation quickly developed into a practical method to generate Cu-Si reagents These silicon nucleophiles cleanly add to aldehyde-derived imine electrophiles to form R-silylated amines in protic media, and no carbon-tonitrogen Brook-type rearrangement of the intermediate anion is observed. Aside from electron-withdrawing groups at the imine nitrogen atom, for example, SO2Tol and P(O)Ph2, previously delicate nitrogen substituents such as phenyl or benzhydryl are tolerated. The same protocol also allows the unprecedented addition to representative ketone-derived imines.
- Vyas, Devendra J.,Froehlich, Roland,Oestreich, Martin
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supporting information; experimental part
p. 2094 - 2097
(2011/06/22)
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- Highly enantioselective Rh-catalyzed transfer hydrogenation of N-sulfonyl ketimines
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Several imine species comprising N-sulfinyl and N-sulfonyl ketimine, oxime, and enamine derivatives were subjected to asymmetric transfer hydrogenation in an azeotropic mixture of formic acid/triethylamine. Among them, the Rh-catalyzed transfer hydrogenat
- Kwak, Se Hun,Lee, Sun Ah,Lee, Kee-In
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experimental part
p. 800 - 804
(2010/10/21)
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- (PPh3)AuCl/AgOTf-catalyzed intermolecular hydroamination of alkynes with sulfonamides to form N-sulfonyl imines
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In the presence of a catalytic amount of (PPh3)AuCl and AgOTf, intermolecular hydroamination of unactivated alkynes with sulfonamides has been shown to proceed and give N-sulfonyl ketimines in medium to excellent yields.
- Cui, Dong-Mei,Zheng, Jin-Zhou,Yang, Liu-Yang,Zhang, Chen
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supporting information; experimental part
p. 809 - 811
(2010/06/22)
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- Green, Catalyst-Free Protocol for the Efficient Synthesis of N-Sulfonyl Aldimines and Ketimines in Ionic Liquid [Bmim]Br
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Sulfonamides are efficiently condensed with aldehydes as well as ketones in the absence of catalyst in 1-butyl-3-methylimidazolium bromide ([bmim]Br) under microwave irradiation to afford N-sulfonyl aldimines and ketimines in good to excellent yields in s
- Zare, Abdolkarim,Moosavi-Zare, Ahmad Reza,Hasaninejad, Alireza,Parhami, Abolfath,Khalafi-Nezhad, Ali,Beyzavi, Mohammad Hassan
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experimental part
p. 3156 - 3165
(2009/11/30)
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- Triazole-Au(I) complexes: A new class of catalysts with improved thermal stability and reactivity for intermolecular alkyne hydroamination
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(Chemical Equation Presented) A series of 1,2,3-triazole-bound cationic Au(I) catalysts have been synthesized, and their structures have been characterized by X-ray crystallography. Variable-temperature NMR studies revealed dynamic triazole-Au cation coor
- Duan, Haifeng,Sengupta, Sujata,Petersen, Jeffrey L.,Akhmedov, Novruz G.,Shi, Xiaodong
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supporting information; experimental part
p. 12100 - 12102
(2009/12/30)
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- Triarylmethyl chlorides as novel, efficient, and mild organic catalysts for the synthesis of N-sulfonyl imines under neutral conditions
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A highly efficient procedure for the preparation of N-sulfonyl imines via condensation of sulfonamides with aldehydes as well as ketones in the presence of triarylmethyl chlorides as metal-free organo-catalysts at 40 °C is described. The advantages of thi
- Khalafi-Nezhad, Ali,Parhami, Abolfath,Zare, Abdolkarim,Shirazi, Amir Nasrolahi,Zare, Ahmad Reza Moosavi,Hassanimejad, Alireza
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p. 456 - 461
(2008/09/20)
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- Sulfonylimidates as nucleophiles in catalytic addition reactions
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The first catalytic addition reactions of sulfonylimidates have been accomplished. In the presence of a catalytic amount of DBU (normally 5-10 mol %), sulfonylimidates reacted with several N-protected imines, methyl acrylate, and azodicarboxylate to afford the corresponding addition adducts, sulfonylimidates, in excellent yields. In the addition reactions to imines, high anti-selectivity was observed. A novel direct formation of β-amino acid derivatives from aldehyde and sulfonylimidate is also described. Copyright
- Matsubara, Rvosuke,Berthiol, Florian,Kobayashi, Shu
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p. 1804 - 1805
(2008/09/18)
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- Highly enantioselective Pd-catalyzed asymmetric hydrogenation of activated imines
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(Chemical Equation Presented) Pd/bisphosphines complexes are highly effective catalysts for asymmetric hydrogenation of activated imines in trifluoroethanol. The asymmetric hydrogenation of N-diphenylphosphinyl ketimines 3 with Pd(CF3CO2)/(S)-SegPhos indicated 87-99% ee, and N-tosylimines 5 could gave 88-97% ee with Pd-(CF3CO 2)/(S)-SynPhos as a catalyst. Cyclic N-sulfonylimines 7 and 11 were hydrogenated to afford the useful chiral sultam derivatives in 79-93% ee, which are important organic synthetic intermediates and structural units of agricultural and pharmaceutical agents.
- Wang, You-Qing,Lu, Sheng-Mei,Zhou, Yong-Gui
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p. 3729 - 3734
(2008/02/04)
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- A novel method for the synthesis of N-sulfonylaldimines by ZnO as a recyclable neutral catalyst under solvent-free conditions
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ZnO acts as an effective catalyst for the rapid synthesis of a range of N-sulfonylaldimines from aromatic aldehydes and sulfonamides under solvent free conditions. The ZnO powder can be reused up to three times after simple washing with distilled water and ethyl acetate.
- Hosseini-Sarvari, Mona,Sharghi, Hashem
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p. 2125 - 2130
(2008/02/08)
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- A highly enantioselective, Pd-TangPhos-catalyzed hydrogenation of N-tosylimines
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(Chemical Equation Presented) A catalyst system composed of Pd-(OCOCF 3)2 complexed with the electron-donating, rigid chiral diphosphane Tang-Phos gives excellent enantioselectivities (up to 99% ee) and conversions (up to > 99%) in the hydrogenation of N-tosylimines 1 (see scheme). A variety of aromatic, aliphatic, and cyclic chiral amines 2 can be prepared by this methodology.
- Yang, Qin,Shang, Gao,Gao, Wenzhong,Deng, Jingen,Zhang, Xumu
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p. 3832 - 3835
(2007/10/03)
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- Asymmetric Strecker reaction of ketoimines catalyzed by a novel chiral bifunctional N,N′-dioxide
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A novel bifunctional N,N′-dioxide derived from L-prolinamide was employed to catalyze the enantioselective Strecker reaction of a range of N-tosyl ketoimines, and an effective additive was used to improve the reactivity (up to 99% yield) as well as the en
- Huang, Xiao,Huang, Jinglun,Wen, Yuehong,Feng, Xiaoming
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p. 2579 - 2584
(2007/10/03)
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- A new general method for the preparation of N-sulfonyloxaziridines
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(Chemical Equation Presented) A simple procedure to obtain N-alkylsulfonyl- and N-arylsulfonyloxaziridines from the corresponding N-sulfinylimines involving a one-pot, two-step oxidation process with m-CPBA (1 equiv) and m-CPBA/KOH (1.1 equiv) is reported
- Garcia Ruano, Jose Luis,Aleman, Jose,Fajardo, Cristina,Parra, Alejandro
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p. 5493 - 5496
(2007/10/03)
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- A general method for the preparation of N-sulfonyl aldimines and ketimines
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(Chemical Equation Presented) A simple procedure to obtain N-sulfonyl imines involving the condensation of carbonyl compounds with p-tolyl or tert-butyl sulfinamides followed by oxidation with m-CPBA of the resulting N-sulfinylimines is reported. The meth
- García Ruano, José Luis,Alemán, José,Cid, M. Belén,Parra, Alejandro
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p. 179 - 182
(2007/10/03)
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- Aerobic oxidative amination of unactivated alkenes catalyzed by palladium
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The first examples of palladium-catalyzed oxidative amination of unactivated alkyl olefins have been identified. To be successful, these reactions must be conducted under cocatalyst-free conditions that involve direct dioxygen-coupled turnover of the palladium catalyst. The oxidative amination products of norbornene and other cyclic alkenes implicate a cis-aminopalladation mechanism. Copyright
- Brice, Jodie L.,Harang, Jenna E.,Timokhin, Vitaliy I.,Anastasi, Natia R.,Stahl, Shannon S.
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p. 2868 - 2869
(2007/10/03)
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- Dioxygen-Coupled Oxidative Amination of Styrene
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Dioxygen-coupled oxidative amination of olefins is an attractive, but challenging, catalytic transformation. The present work describes the first general method for intermolecular oxidative amination of aryl olefins with molecular oxygen as the stoichiometric oxidant. This palladium-catalyzed reactivity is compatible with several different nitrogen nucleophiles, including oxazolidinone, phthalimide, pyrrolidinone, and p-toluenesulfonamide. The presence of a catalytic quantity of a Bronsted base in the reaction increases the catalytic activity and switches the reaction regioselectivity. Copyright
- Timokhin, Vitaliy I.,Anastasi, Natia R.,Stahl, Shannon S.
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p. 12996 - 12997
(2007/10/03)
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- 3,3-Disubstituted 2-Sulphonyloxaziridines: Synthesis and Observation of Isomeric Nitrogen Invertomers
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The synthesis of the title compounds from oximes is described; some of these compounds provide the first reported examples of cis-trans isomerism in N-sulphonyloxaziridines.
- Jennings, W. Brian,Watson, Stephen P.,Boyd, Derek R.
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p. 931 - 932
(2007/10/02)
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- Thione S-Imides. The Reaction with Carbon-Hetero Atom Double Bond
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9-Fluorenethione S-p-toluenesulfonimide reacted as a 1,3-dipole with imines, oximes, and thiones to form (3+2)cycloadducts, while with symmetrical azines and aldehydes, unsymmetrical azines, N-(p-tolylsulfonyl)imines and fluorenone were obtained as a result of the decomposition of the cycloadducts.
- Saito, Takao,Oikawa, Isao,Motoki, Shinichi
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p. 1023 - 1027
(2007/10/02)
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