- PROCESS FOR THE PREPARATION OF ARYLSULFONYLPROPENENITRILES
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The present invention relates to a process for the preparation of arylsulfonylpro- penenitriles. The reaction starting from arylsulfonyl halides is catalyzed by a cat- alyst compound comprising a transition metal. The process is scalable, environ- mentally benign and provides the product in good yield.
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Page/Page column 9
(2020/06/01)
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- PROCESS FOR THE PREPARATION OF ARYLSULFONYLPROPENENITRILES BY PHOTOCATALYTIC REACTIONS
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The present invention relates to a process for the preparation of arylsulfonylpro- penenitriles. The reaction starting from arylsulfonyl iodides is catalyzed by light. The process is scalable, environmentally benign and provides the product in good yield.
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Page/Page column 11
(2019/03/17)
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- Catalytic Hydrocyanation of Activated Terminal Alkynes
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A universal, practical and scalable organocatalytic hydrocyanation manifold to provide β-substituted acrylonitriles bearing an electron-withdrawing functionality has been implemented. The catalytic manifold operates under the reactivity generation principle “a good nucleophile generates a strong base”, and it uses 1,4-diazabicyclo[2.2.2]octane (DABCO) as the catalyst, activated terminal alkynes as substrates and acetone cyanohydrin as the cyanide source. The acrylonitriles obtained as E,Z mixtures are straightforwardly resolved by simple flash chromatography delivering the pure isomers in preparative amounts.
- Tejedor, David,Delgado-Hernández, Samuel,Colella, Lucía,García-Tellado, Fernando
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supporting information
p. 15046 - 15049
(2019/11/22)
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- Copper-catalyzed aerobic oxidative N-S bond functionalization for C-S bond formation: Regio- and stereoselective synthesis of sulfones and thioethers
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A regio- and stereoselective synthesis of sulfones and thioethers by means of CuI-catalyzed aerobic oxidative N-S bond cleavage of sulfonyl hydrazides, followed by cross-coupling reactions with alkenes and aromatic compounds to form the C-sp-2-S bond, is described herein. N2 and H2O are the byproducts of this transformation, thus offering an environmentally benign process with a wide range of potential applications in organic synthesis and medicinal chemistry. First cleave, then cross-couple: A direct Cu-catalyzed aerobic oxidative C-sp-2-H functionalization and C-S bond coupling reaction has been developed (see scheme). By slight modification of the additive, sulfonyl hydrazides could serve as sulfonation, sulfenation, or arylation reagents to undergo cross-coupling reactions with alkenes and (hetero)aromatic cycles, affording sulfones, thioethers, and biaryl compounds with high regio- and stereoselectivities (see scheme).
- Li, Xianwei,Xu, Yanli,Wu, Wanqing,Jiang, Chang,Qi, Chaorong,Jiang, Huanfeng
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supporting information
p. 7911 - 7915
(2014/07/07)
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- An improved synthesis of vinyl- and β-iodovinyl sulfones by a molecular iodine-mediated one-pot iodosulfonationdehydroiodination reaction
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An improved one-pot method to synthesize vinyl sulfones from unsaturated systems by using molecular iodine/sodium arenesulfinate/sodium acetate as reagents was described. Vinyl sulfones derived from styrene derivatives were generally obtained in good to excellent yields except for those bearing strong electron releasing substituent. Aliphatic alkenes and activated alkenes gave the corresponding vinyl sulfone products in moderate to good yields. Arylacetylenes yielded the respective β-iodovinyl sulfones in good yields while low yield was observed with aliphatic terminal alkyne. The potentials of the method entail simplicity, short reaction time, non-anhydrous reaction conditions, employing inexpensive, non-metallic reagent and integrating two reactions that are commonly accomplished separately into a single operation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Sawangphon, Tassaporn,Katrun, Praewpan,Chaisiwamongkhol, Korbua,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Soorukram, Darunee,Kuhakarn, Chutima
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supporting information
p. 1692 - 1707
(2013/05/22)
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- PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones
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(Diacetoxyiodo)benzene [PhI(OAc)2, DIB] was able to promote the reaction of sodium aryl sulfinate and potassiumiodide (KI) with alkenes and alkynes to afford the corresponding vinyl sulfones and β-iodovinyl sulfones, respectively, in good yield
- Katrun, Praewpan,Chiampanichayakul, Supanimit,Korworapan, Kanokwan,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Kuhakarn, Chutima
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supporting information; experimental part
p. 5633 - 5641
(2010/12/25)
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- Facile method for solid-phase synthesis of vinyl sulfones using polystyrene-supported selenomethyl aryl sulfone
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Treatment of novel polystyrene-supported selenomethyl aryl sulfone with LDA followed by alkylation and oxidation elimination efficiently afforded vinyl sulfones in good yields and purities.
- Sheng, Shou-Ri,Zhou, Wei,Zhong, Ming-Hua,Liu, Xiao-Ling,Chen, Hui-Zong
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p. 815 - 821
(2007/10/03)
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- Polystyrene-Supported α-Seleno Carbanions: Efficient Reagents for Highly Stereocontrolled Syntheses of Vinylphosphonates and Vinylsulfones
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Polystyrene-supported selenomethyl-phosphonate and polystyrene-supported selenomethyl-sulfonates have been prepared. These novel reagents were treated with LDA (or n-BuLi) to produce polystyrene-supported α-seleno carbanions, which reacted with alkyl halides, followed by stereospecific selenoxide syn-elimination to give E-vinylphosphonates and E-vinylsulfones respectively. And also these novel polymer reagents can be regenerated and reused.
- Xu, Wei Ming,Tang, E,Huang, Xian
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p. 2094 - 2098
(2007/10/03)
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- Polystyrene-supported selenosulfonates: Efficient reagents for regio- and stereocontrolled synthesis of vinyl sulfones
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Two novel polystyrene-supported selenosulfonates reagents have been developed. As reagents for boron trifluoride catalyzed or AIBN catalyzed addition to olefins were successfully demonstrated and have been used for regioselective synthesis of vinyl sulfon
- Qian,Huang
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p. 1913 - 1916
(2007/10/03)
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- Regio- and Stereo-selective Synthesis of β-Sulphonyl-α,β-Unsaturated Carbonyl Compounds via an Iodosulphonylation-Dehydroiodination Raction
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α,β-Unsaturated carbonyl compounds underwent regiospecific iodosulphonylation with toluene-p-sulphonyl iodide or sodium toluene-p-sulphinate and iodine to afford products (2), which were stereoselectively dehydroiodinated by triethylamine to give β-sulphonyl derivatives (3).The reactivity of compounds (3) as cationic β-acylvinyl equivalents, tested with amines or thiophenol, gave compounds (4) resulting from a displacement reaction.
- Najera, Carmen,Baldo, Beatriz,Yus, Miguel
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p. 1029 - 1032
(2007/10/02)
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- Substitution Reactions of Carbon Nucleophiles with β-(Phenylseleno)vinyl Sulfone Se Oxides
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Selenoxides 2, obtained from the selenosulfonation and peracid oxidation of acetylenes, reacted with various nucleophiles to afford the products of overall substitution of the PhSeO moiety.Anions of dimethyl malonate, ethyl acetoacetate, malononitrile, 1-
- Back, Thomas G.,Krishna, M. Vijaya
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p. 4265 - 4269
(2007/10/02)
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- Selenosulfonation: Boron Trifluoride Catalyzed or Thermal Addition of Selenosulfonates to Olefins. A Novel Regio- and Stereocontrolled Synthesis of Vinyl Sulfones.
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Se-Phenyl areneselenosulfonates 1 add to a variety of olefins to produce β-phenylseleno sulfones 2.The reaction may be performed in the presence of boron trifluoride etherate to produce chiefly or exclusively Markovnikov products arising from a stereospecific anti addition.Alternatively, the addition may be thermally induced to afford anti-Markovnikov products generated by a nonstereospecific free-radical process.The two modes of addition achieve complementary regiospecificity.The β-phenylseleno sulfones are converted in high yield to vinyl sulfones by stereospecific oxidation-elimination with m-chloroperbenzoic acid.
- Back, Thomas G.,Collins, Scott
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p. 3249 - 3256
(2007/10/02)
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