- Iodine-Promoted Deoxygenative Iodization/Olefination/Sulfenylation of Ketones with Sulfonyl Hydrazides: Access to β-Iodoalkenyl Sulfides
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A highly regio- and stereoselective synthesis of β-haloalkenyl sulfides using commercially available ketones and sulfonyl hydrazides as starting materials has been developed. This protocol obviates the need for alkynes and traditional sulfenylating agents
- Bao, Yishu,Yang, Xiuqin,Zhou, Qingfa,Yang, Fulai
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- Synthesis of (E)-β-iodovinyl sulfones via DTBP/I2 promoted difunctionalization of alkynes with sodium benzenesulfinates
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The present reaction provides a simple and convenient synthetic strategy to construct β-iodovinyl sulfones through molecular iodine and DTBP (di-tert-butyl peroxide) promoted difunctionalization of alkynes with sodium benzenesulfinates under mild and envi
- Bi, Wenzhu,Ren, Chunyan,Jia, Linguo,Xia, Xiaoyi,Chen, Xi,Chen, Xiaolan,Zhao, Yufen
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- Transition-metal-free NaI-mediated reaction of aryl sulfonyl chloride with alkynes: Synthesis of (E)-β-iodovinyl sulfones
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A novel protocol for synthesis of (E)-β-Iodovinyl sulfones via NaI-mediated of aryl sulfonyl chloride with alkynes is described, featuring transition-metal-free condition, commercial available substrates, convenient operation, as well as good functional group compatibility. A wide variety of substrate application and good functional group tolerance is provided by this approach, giving multiple (E)-β-Iodovinyl sulfones analogues with excellent yields (up to 98%, >4 g scale).
- Chen, Dan,Lin, Li,Peng, Xiaoyan,Yu, Xinyi,Yang, Zhonglie,Liu, Yutong,Zhang, Xiaobin,Li, Jiahong,Jiang, Hezhong
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supporting information
(2021/06/15)
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- Visible-light-induced surfactant-promoted sulfonylation of alkenes and alkynes with sulfonyl chloride by the formation of an EDA-complex with NaI in water at room temperature
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A green and efficient visible-light-induced iodosulfonyl reaction of alkenes in water using an EDA complex strategy at room temperature has been disclosed. The addition of a cationic surfactant allows for the easy formation of colored EDA complexes in water. The hydrophobic effect of the core in the surfactant aggregates, which act as a reaction medium formed by the surfactants themselves in water, plays a significant role in stabilizing the transition state and decreasing the activation energy of the reaction. Remarkably, transition-metal catalysts and organic solvents were not required in this transformation. Moreover, it displayed a broad substrate scope, good functional group tolerance, simple operation, scalability and high chemical selectivity. Thus, it not only provided a green and efficient synthetic strategy for the preparation of β-iodo-substituted sulfone derivatives, but also enriched the investigation of visible-light-induced reactions in water.
- Jiang, Hezhong,Li, Jiahong,Li, Jun-Long,Lin, Li,Liu, Jianchen,Liu, Xiang-Wei,Wang, Jingxia,Yang, Zhonglie,Zhang, Xiaobin,Zheng, Jiale
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p. 5467 - 5473
(2021/08/16)
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- Synthesis of (E)-iodo vinylsulfones via oxidative addition of thiol into alkyne under metal free condition
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An efficient, transition-metal free and molecular iodine promoted protocol for the construction of (E)-β-iodovinyl sulfone derivatives via oxidative C–S coupling of thiol and alkyne has been demonstrated. Both aryl and alkyl terminal acetylenes were found to be an excellent substrate for the present reaction which provides a wide range of β-iodovinyl sulfone derivatives with very good yield and excellent regio and stereo-selectivities. Diaryldisulfide is also found to be an equally efficient sulfonyl group surrogate under identical reaction conditions.
- Samanta, Surya Kanta,Sarkar, Rumpa,Bera, Mrinal K.
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supporting information
(2021/07/12)
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- An iodine-mediated new avenue to sulfonylation employingN-hydroxy aryl sulfonamide as a sulfonylating agent
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A novel and highly efficient I2/K2CO3mediated regioselective sulfonylation of thiophenols, aryl acetylenic acid and aromatic alkynes withN-hydroxy sulfonamide has been developed.N-hydroxy sulfonamide has been used for the first time for the synthesis of these sulfones. The scope and versatility of the reaction has been demonstrated by the regio- and stereoselective synthesis of different analogs of sulfones with various structural features.
- Raghuvanshi, Dushyant Singh,Verma, Narsingh
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supporting information
p. 4760 - 4767
(2021/06/09)
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- Iodosulfonylation of Alkynes under Ultrasound Irradiation
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(E)-Iodo vinylsulfones are synthesized under ultrasound irradiation using alkynes, sulfonyl hydrazides, potassium iodide and hydrogen peroxide. The key features of this protocol are the speed and efficiency of the reactions, which afford good to excellent
- Zhou, Chuanjiang,Zeng, Xianghua
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p. 4614 - 4620
(2021/09/13)
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- Electrochemical Induced Regio- and Stereoselective Difunctionalization of Alkynes: The Synthesis of (E)-β-Iodovinyl Sulfones
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An efficient, green, and oxidant-free electrochemical method for alkyne difunctionalization was described. Using undivided electrochemical cell for iodosulfonylation of alkynes with commercially available iodide radical (NaI), arylsulfonyl radical (ArSOs
- Zhang, Xinghua,Lu, Danna,Wang, Zhenwei
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supporting information
p. 4284 - 4287
(2021/06/16)
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- Introduction of N,N'-disulfonylhydrazines as new sulfonylating reagents for highly efficient synthesis of (E)-β-iodovinyl arenesulfones under mild conditions
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N,N'-Disulfonylhydrazines have been proven to be the most reactive precursors of the sulfonyl radicals among all types of sulfonyl substituted hydrazines as early as half a century ago. However, the sulfonyl radicals generated from these compounds have no
- Luo, Dongping,Min, Lin,Zheng, Weiping,Shan, Lidong,Wang, Xinyan,Hu, Yuefei
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p. 1877 - 1880
(2020/01/21)
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- Electrochemically enabled sulfonylation of alkynes with sodium sulfinates
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An electrochemical sulfonylation of alkynes with sodium sulfinates was achieved for the first time at room temperature. Employing this electrolysis strategy, the reaction occurs efficiently under transition-metal-free, external oxidant-free, and base-free conditions and furnishes diverse alkynyl sulfones in satisfactory yield with broad functional group tolerance.
- Meng, Xiangtai,Xu, Hehua,Cao, Xiaoji,Cai, Xu-Min,Luo, Jinyue,Wang, Fei,Huang, Shenlin
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supporting information
p. 6827 - 6831
(2020/09/15)
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- Pd-Catalyzed Annulation of β-Iodovinyl Sulfones with 2-Halophenols: A General Route for the Synthesis of 3-Sulfonyl Benzofuran Derivatives
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The palladium-catalyzed annulation between β-iodovinyl sulfones and 2-halophenols or 1-bromo-2-naphthol or 2-bromo-3-pyridinol is presented. The annulation process involving oxa-Michael addition-elimination and intramolecular Heck reaction leading to form
- Krishna, Gamidi Rama,Kumar, Jangam Jagadesh,Kumari, Arram Haritha,Reddy, Raju Jannapu
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supporting information
(2020/03/04)
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- Solvent Controlled Transformation between Sulfonyl Hydrazides and Alkynes: Divergent Synthesis of Benzo[b]thiophene-1,1-dioxides and (E)-β-iodo Vinylsulfones
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A green, efficient and controllable transformation between sulfonyl hydrazides and alkynes leading to benzo[b]thiophene-1,1-dioxides and (E)-β-iodo vinylsulfones via radical pathway has been developed. The reaction occurs rapidly in the presence of simply H2O2 and KI without the help of any transition metal. The chemoselectivity of the reaction is determined by the solvent in which the process is performed: TFE favors the cyclic product, while H2O medium generates the iodosulfonylative product. Notably, this protocol also represents the first direct approach to the aggregation-induced-emmision (AIE) active benzo[b]thiophene-1,1-dioxides from readily available sulfonyl hydrazides and alkynes in one step. (Figure presented.).
- Ma, Yue,Wang, Kun,Zhang, Dong,Sun, Peng
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p. 597 - 602
(2018/12/13)
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- Unprecedented Reactivity of β-Iodovinyl Sulfones: An Efficient Synthesis of β-Keto Sulfones and β-Keto Thiosulfones
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An unprecedented reactivity of (E)-β-iodovinyl sulfones in the presence of NaOAc is reported. The (E)-β-iodovinyl sulfones were treated with NaOAc in DMSO/H2O to yield β-keto sulfones in moderate to high yields. A novel oxidative difunctionalization of β-iodovinyl sulfones with thiosulfonates and NaOAc in DMF has been developed. This metal-free oxosulfenylation is an operationally simple to access a wide range of β-keto thiosulfones (α-thioaryl-β-keto sulfones) in moderate to high yields. The transformations were reliable at gram-scale, thus illustrating its efficiency and practicality. A plausible mechanism for the protocol is also proposed.
- Reddy, Raju Jannapu,Kumar, Jangam Jagadesh,Kumari, Arram Haritha
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supporting information
p. 3771 - 3775
(2019/06/24)
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- Synthetic method of beta-iodo-alkenyl sulfone compound
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The invention discloses a synthetic method of a beta-iodo-alkenyl sulfone compound. The synthesis method comprises the following steps: mixing an alkyne derivative, a sulfonyl hydrazine derivative, iodine pentoxide and a solvent to obtain a mixed solution
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Paragraph 0061; 0062; 0063
(2019/01/07)
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- Iodine promoted iodosulfonylation of alkynes with sulfonyl hydrazides in an aqueous medium: Highly stereoselective synthesis of (E)-β-iodo vinylsulfones
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A catalyst-free and metal-free sulfonylation reaction for the preparation of (E)-β-iodo vinylsulfones from alkynes with sulfonyl hydrazides and molecular iodine was efficiently developed under mild and environmentally benign conditions, in water without any ligand or catalyst. The reaction gave a range of structurally diverse β-iodo vinylsulfones with excellent E selectivities and high yields.
- Hou, Yunlei,Zhu, Liangyu,Hu, Hao,Chen, Shaowei,Li, Zefei,Liu, Yajing,Gong, Ping
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supporting information
p. 8752 - 8755
(2018/06/08)
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- Cobalt-catalyzed stereoselective iodosulfonylation and diiodination of alkynes via oxidation of potassium iodide in air
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Cobalt-catalyzed iodosulfonylation of alkynes can be achieved using sodium sulfinates in the presence of KI. This procedure produces numerous stereoselective (E)-β-iodoalkenyl sulfones with good yields and suppresses the formation of diiodoalkenes. Furthermore, when this reaction is performed in the absence of sodium sulfinates, the expected (E)-diiodoalkenes are obtained.
- Taniguchi, Nobukazu
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p. 1454 - 1460
(2018/02/15)
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- TBAI/K2S2O8-facilitated reaction of sulfonylhydrazides with alkynes: Facile synthesis of (E)-β-iodovinyl sulfones
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An efficient and convenient approach for the construction of various (E)-β-iodovinyl sulfones has been developed through potassium persulfate/tetrabutylammonium iodide-facilitated reaction of sulfonylhydrazides with alkynes. The products were obtained in good to excellent yields. The salient features of this reaction are the applications of a new iodine source, environmentally benign, safer solid oxidant, and shorter reaction time.
- Tong, Chuo,Gan, Bing,Yan, Yiyan,Xie, Yuan-Yuan
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p. 1927 - 1933
(2017/10/06)
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- Generation of β-Halo Vinylsulfones through a Multicomponent Reaction with Insertion of Sulfur Dioxide
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A four-component reaction of terminal alkynes, aryldiazonium tetrafluoroborates, sulfur dioxide surrogate of DABCO?(SO2)2, and potassium halide in the presence of copper(I) chloride (10 mol %) gives rise to β-halo vinylsulfones with good stereoselectivity. The vicinal difunctionalization of alkynes through sulfonylation and halogenation with the insertion of sulfur dioxide works efficiently. A plausible mechanism is proposed, which includes a radical process.
- Xiang, Yuanchao,Kuang, Yunyan,Wu, Jie
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p. 6996 - 6999
(2017/05/29)
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- Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent
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A novel iodine-catalyzed functionalization of a variety of olefins and alkynes and direct decarboxylative functionalization of cinnamic and propiolic acids with TosMIC to provide access to various vinyl, allyl, and β-iodo vinylsulfones is described. This simple, efficient, and environmentally benign approach employing inexpensive molecular iodine as a catalyst demonstrates a versatile protocol for the synthesis of highly valuable sulfones, rendering it attractive to both synthetic and medicinal chemistry.
- Kadari, Lingaswamy,Palakodety, Radha Krishna,Yallapragada, Lakshmi Prapurna
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supporting information
p. 2580 - 2583
(2017/05/24)
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- Synthesis of (: E)-β-iodo vinylsulfones via iodine-promoted iodosulfonylation of alkynes with sodium sulfinates in an aqueous medium at room temperature
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An efficient molecular iodine-promoted method for the synthesis of (E)-β-iodo vinylsulfones using water as the solvent at room temperature has been developed. This green reaction is fast, operationally simple, environmentally benign and, especially, proceeds under very mild conditions to afford the target products with high regio- and stereoselectivity.
- Sun, Yadong,Abdukader, Ablimit,Lu, Dong,Zhang, Haiyan,Liu, Chenjiang
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supporting information
p. 1255 - 1258
(2017/08/15)
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- Iodine-catalyzed Sulfonylation of Arylacetylenic Acids and Arylacetylenes with Sodium Sulfinates: Synthesis of Arylacetylenic Sulfones
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A highly efficient and generally applicable iodine-catalyzed reaction of arylacetylenic acids and arylacetylenes with sodium sulfinates for the synthesis of arylacetylenic sulfones was developed. The methodology has the advantages of a metal-free strategy, easy to handle reagents, functional group tolerance, a wide range of arylacetylenic acids and arylacetylenes, and easy access to arylacetylenic sulfones. (Chemical Equation Presented).
- Meesin, Jatuporn,Katrun, Praewpan,Pareseecharoen, Chayaporn,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Kuhakarn, Chutima
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p. 2744 - 2752
(2016/04/26)
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- Direct, Sequential, and Stereoselective Alkynylation of C,C-Dibromophosphaalkenes
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The first direct alkynylation of C,C-dibromophosphaalkenes by a reaction with sulfonylacetylenes is reported. Alkynylation proceeds selectively in the trans position relative to the P substituent to afford bromoethynylphosphaalkenes. Owing to the absence
- Shameem, Muhammad A.,Esfandiarfard, Keyhan,?berg, Elisabet,Ott, Sascha,Orthaber, Andreas
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supporting information
p. 10614 - 10619
(2016/07/21)
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- Odorless, One-Pot Regio- and Stereoselective Iodothiolation of Alkynes with Sodium Arenesulfinates under Metal-Free Conditions in Water
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A newly developed regio- and stereoselective radical addition of alkyne under metal-free conidtions has been disclosed. This chemistry, in which odorless sodium arenesulfinates in place of thiols are used as the sulfur reagent, provides an efficient, one-pot approach for the generation of β-iodoalkenyl sulfides, which can be easily further functionalized to derive various alkenes and alkynyl sulfides rendering this methodology attractive to both synthetic and medicinal chemistry. (Chemical Equation Presented).
- Lin, Ya-Mei,Lu, Guo-Ping,Cai, Chun,Yi, Wen-Bin
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supporting information
p. 3310 - 3313
(2015/07/15)
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- Direct difunctionalization of alkynes with sulfinic acids and molecular iodine: A simple and convenient approach to (E)-β-iodovinyl sulfones
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A simple and convenient approach for the construction of β-iodovinyl sulfones has been developed via direct difunctionalization of alkynes with sulfinic acids and molecular iodine. The present reaction provides a highly efficient approach to a diverse range of substituted (E)-β-iodovinyl sulfones in moderate to good yields with excellent stereo- and regio-selectivities but no need for any metal catalyst or additives.
- Wei, Wei,Wen, Jiangwei,Yang, Daoshan,Jing, Huijun,You, Jinmao,Wang, Hua
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p. 4416 - 4419
(2015/02/19)
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- N-Methylpyrrolidone Hydroperoxide/Cs2CO3 as an Excellent Reagent System for the Hydroxy-Directed Diastereoselective Epoxidation of Electron-Deficient Olefins
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This report introduces N-methylpyrrolidone hydroperoxide (NMPOOH)/base as an excellent reagent system for hydroxy-directed syn selective epoxidation of electron-deficient olefins, characterized by high diastereoselectivity, short reaction times and remarkable chemoselectivity, especially in presence of oxidatively labile nitrogen or sulfur atoms. NMPOOH also proves efficient in the oxidation of electron-deficient aromatic aldehydes, in the removal of oxazolidinone chiral auxiliary, and in the functionalization of alkenes and alkynes, showing wide application potential. Something kinda HOO-: This report introduces N-methylpyrrolidone hydroperoxide/base as an excellent system for the hydroxy-directed syn-selective epoxidation of electron-deficient olefins, characterized by high diastereoselectivity, short reaction times and remarkable chemoselectivity, especially in the presence of oxidatively labile nitrogen or sulfur atoms.
- Victor, Napoleon John,Gana, Janardhanan,Muraleedharan, Kannoth Manheri
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supporting information
p. 14742 - 14747
(2015/10/19)
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- Aerobic copper-catalyzed synthesis of (E)-alkenyl sulfones and (E)-β-halo-alkenyl sulfones via addition of sodium sulfinates to alkynes
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Copper-catalyzed sulfonylation of alkynes using sodium sulfinates in air produced regio- and stereoselectively (E)-alkenyl sulfones. When a CuCl catalyst was employed, the hydrosulfonylation proceeded syn-selectively, and (E)-alkenyl sulfones were synthesized in excellent yields. In contrast, the reaction using CuI catalyst produced (E)-β-haloalkenyl sulfones anti-selectively in the presence of potassium halides. Furthermore, the (E)-β-bromoalkenyl sulfones are possible to convert into various alkenyl sulfones by Suzuki-Miyaura coupling.
- Taniguchi, Nobukazu
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supporting information
p. 1984 - 1990
(2014/03/21)
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- I2/TBHP-mediated reaction of sulfonylhydrazides with alkynes: Synthesis of (E)-β-iodovinyl sulfones
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An efficient and simple procedure for the syntheses of (E)-β-iodovinyl sulfones through TBHP mediated reaction of sulfonylhydrazides and iodine with aryl acetylenes has been developed. This method offers several advantages such as high atom economy, envir
- Li, Xiaoqing,Xu, Xiangsheng,Shi, Xinhua
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supporting information
p. 3071 - 3074
(2013/06/27)
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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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- CAN mediated reaction of aryl sulfinates with alkenes and alkynes: Synthesis of vinyl sulfones, β-iodovinyl sulfones and acetylenic sulfones
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Cerium(IV) ammonium nitrate (CAN) mediated reaction of aryl sulfinates and sodium iodide with alkenes afforded vinyl sulfones in very good yields. Alkynes underwent similar reaction to give β-iodovinyl sulfones, which on treatment with potassium carbonate
- Nair, Vijay,Augustine, Anu,Suja
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p. 2259 - 2265
(2007/10/03)
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- An efficient one-pot synthesis of vinyl sulphones via CAN mediated reaction of aryl sulphinates and alkenes
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Cerium(IV) ammonium nitrate mediated reaction of sodium arene sulphinate and sodium iodide with alkenes afforded vinyl sulphones in very good yields.
- Nair, Vijay,Augustine, Anu,George, Tesmol G,Nair, Latha G
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p. 6763 - 6765
(2007/10/03)
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- Addition of Arenesulphonyl Iodides to Substituted Phenylacetylenes
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The products of the addition of toluene-p-sulphonyl iodide to substituted phenylacetylenes (and styrenes) are studied.The regiospecificity and stereoselectivity of trans addition to acetylenes is inferred from (1)H n.m.r. spectroscopy.The effect of substituents on the reactivity of substituted phenylacetylenes towards substituted beenzenesulphonyl radicals generated by photolysis of sulphonyl iodides is studied.Phenylacetylenes with electron-donating substituents react faster.Relative reactivities yield good Hammet-Brown correlations showing the electrophilic character of sulphonyl radicals towards phenylacetylenes.The selectivity of the addition (measured by ρ) of different sulphonyl radicals towards the same set of acetylenes ranges from -0.53 to -0.93 and shows a tendency to be smaller for benzenesulphonyl iodides carrying electron donating substituents.Results are discussed in terms of polar effects on the transition state and frontier molecular orbital theory.
- Silva Correa, Carlos M. M. da,Fleming, Maria Daniela C. M.
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p. 103 - 108
(2007/10/02)
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