- Sulphonomercuriation route to vinyl and ethynyl sulphones
-
Ethynyl sulphones were obtained from the reaction of substituted acetylenes with mercury(II) chloride and sodium benzenesulphinate followed by oxidative demercuriation.
- Rajakumar, Perumal,Kannan, Arunachalam
-
-
Read Online
- Boryl Radical-Mediated C?H Activation of Inactivated Alkanes for the Synthesis of Internal Alkynes
-
An intriguing pyridine-boryl radical-mediated C?H alkynylation reaction of inactivated alkanes was described. The reaction features mild operation condition and wide substrate scope, and affords the corresponding products in moderate to good yields. Notab
- Han, Jia-Bin,San, Htet Htet,Guo, Ao,Wang, Long,Tang, Xiang-Ying
-
supporting information
p. 2366 - 2370
(2020/11/30)
-
- Visible-Light-Induced Three-Component Intermolecular Trifluoromethyl-Alkenylation Reactions of Unactivated Alkenes
-
Herein, we describe a practical protocol for efficient, mild, visible-light-induced three-component intermolecular trifluoromethyl-alkenylation reactions of unactivated alkenes. The protocol has good functional group tolerance and a broad substrate scope. Using this protocol, we not only introduced a trifluoromethyl group into alkenes but also converted unactivated alkenes to styrene-based activated alkenes, in addition to accomplishing late-stage functionalization of pharmaceutical intermediates. (Figure presented.).
- Guo, Yuan-Qiang,Wang, Kaihua,Wang, Ruiguo,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
-
supporting information
p. 1651 - 1655
(2021/02/12)
-
- Copper-Catalyzed Intermolecular Alkynylation and Allylation of Unactivated C(sp3)-H Bonds via Hydrogen Atom Transfer
-
We describe Cu-catalyzed intermolecular alkynylation and allylation of unactivated C(sp3)-H bonds with singly occupied molecular orbital-philes (SOMO-philes) via hydrogen atom transfer (HAT). Employing N-fluoro-sulfonamide as a HAT reagent, a set of subst
- Liang, Lei,Guo, Ge,Li, Chen,Wang, Song-Lin,Wang, Yue-Hui,Guo, Hai-Ming,Niu, Hong-Ying
-
supporting information
p. 8575 - 8579
(2021/11/13)
-
- Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation
-
A versatile approach for the alkynylation of a variety of aliphatic hydrogen donors, including alkanes, is reported. We used tetrabutylammonium decatungstate as photocatalyst to generate organoradicals from C-H/Si-H bonds via hydrogen atom transfer. The l
- Capaldo, Luca,Ravelli, Davide
-
p. 2243 - 2247
(2021/04/05)
-
- Visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones
-
Herein we report a mild, general protocol for visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones. The protocol permits efficient functionalization of sulfones with a broad range of cyclic and acyclic secondary and tert
- Dong, Jianyang,Liu, Yuxiu,Wang, Qingmin,Yue, Fuyang
-
supporting information
p. 8924 - 8928
(2021/11/04)
-
- Radical-mediated sulfonyl alkynylation, allylation, and cyanation of propellane
-
Bicyclo[1.1.1]pentane (BCP) is widely applied as the bioisostere for aryl, internal alkynes, andtert-butyl groups in medicinal chemistry. We herein disclose an efficient and practical preparation of sulfonyl alkynyl/allyl/cyano-substituted BCP derivatives
- Wu, Zhen,Xu, Yaohui,Zhang, Huihui,Wu, Xinxin,Zhu, Chen
-
supporting information
p. 6066 - 6069
(2021/06/21)
-
- Synthesis of (E)-iodo vinylsulfones via oxidative addition of thiol into alkyne under metal free condition
-
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.
-
-
- An iodine-mediated new avenue to sulfonylation employingN-hydroxy aryl sulfonamide as a sulfonylating agent
-
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
-
supporting information
p. 4760 - 4767
(2021/06/09)
-
- Electrochemically enabled sulfonylation of alkynes with sodium sulfinates
-
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
-
supporting information
p. 6827 - 6831
(2020/09/15)
-
- Electrochemical decarboxylative sulfonylation of arylacetylenic acids with sodium arylsulfinates: Access to arylacetylenic sulfones
-
An efficient decarboxylative sulfonylation of arylacetylenic acids with sodium arylsulfinates has been achieved by an electro-oxidative strategy. This novel protocol offers a simple, efficient, and green route to a series of arylacetylenic sulfones in mod
- Zhong, Qihao,Zhao, Yongli,Sheng, Shouri,Chen, Junmin
-
supporting information
p. 161 - 167
(2019/12/03)
-
- Mukaiyama reagent-promoted metal-free preparation of alkynyl sulfones and phosphonates under mild conditions
-
An efficient and mild route for the formation sulfur or phosphor-substituted alkynes was herein demonstrated. The Mukaiyama reagent-mediated transformation started from easily-accessible substrates without carbon-carbon triple bonds, and the reaction proceeded under mild conditions (room temperature) in a one-pot manner, requiring for no transition metal-catalysts. The practical protocol featured for good functional groups tolerance (up to 41 examples) and high efficiency (up to 91% yields) towards alkynyl sulfones and alkynyl phosphonates at low cost.
- Qi, Danyang,Dong, Wanrong,Peng, Zhihong,Zhang, Yingjun,An
-
-
- Fixation of CO2 as a carboxylic acid precursor by microcrystalline cellulose (MCC) supported Ag NPs: A more efficient, sustainable, biodegradable and eco-friendly catalyst
-
Silver nanoparticles supported on microcrystalline cellulose (Ag NPs@MCC), an active catalyst, has been discovered for the direct carbonylation of terminal alkynes with CO2 into carboxylic acid under mild and sustainable reaction conditions. The stabilized Ag NPs show higher distribution with a uniform particle size. The catalyst was characterized by PXRD, SEM, TEM, HR-TEM, EDS, EDX, ICP-AES and XPS analysis. The Ag NPs@MCC material was found to be more efficient, shows excellent dispersion in various solvents and is biodegradable. The solvent effects on carbonylation of terminal alkynes were well studied both experimentally and computationally. Furthermore, the present catalyst can be recycled in up to five catalytic cycles without significant loss of its activity and is also applicable for the gram scale carbonylation of terminal alkynes.
- Shah, Dharmesh J.,Sharma, Anuj S.,Shah, Akshara P.,Sharma, Vinay S.,Athar, Mohd,Soni, Jigar Y.
-
p. 8669 - 8676
(2019/06/14)
-
- Visible light-induced co- or cu-catalyzed selenosulfonylation of alkynes: Synthesis of β-(seleno)vinyl sulfones
-
A visible light-induced Co- or Cu-catalyzed selenosulfonylation of alkynes for the synthesis of β-(seleno)vinyl sulfones is demonstrated. This method utilizes a low-cost cobalt salt or metal copper as the catalysts. The reaction goes through a photoinduced free radical addition of selenosulfonates to alkynes for the 1,2-selenosulfonylation of alkynes under mild conditions.
- Ji, Shun-Jun,Wang, Shun-Yi,Xu, Pei,Zhang, Rong
-
-
- Catalyst-Free Deaminative Functionalizations of Primary Amines by Photoinduced Single-Electron Transfer
-
The use of pyridinium-activated primary amines as photoactive functional groups for deaminative generation of alkyl radicals under catalyst-free conditions is described. By taking advantage of the visible light absorptivity of electron donor–acceptor complexes between Katritzky pyridinium salts and either Hantzsch ester or Et3N, photoinduced single-electron transfer could be initiated in the absence of a photocatalyst. This general reactivity platform has been applied to deaminative alkylation (Giese), allylation, vinylation, alkynylation, thioetherification, and hydrodeamination reactions. The mild conditions are amenable to a diverse range of primary and secondary alkyl pyridiniums and demonstrate broad functional group tolerance.
- Wu, Jingjing,Grant, Phillip S.,Li, Xiabing,Noble, Adam,Aggarwal, Varinder K.
-
supporting information
p. 5697 - 5701
(2019/03/21)
-
- Synthesizing method of acetyleic sulfone
-
The invention provides a synthesizing method of acetyleic sulfone. The synthesizing method comprises the following steps of mixing a primer which is shown in the description, 2-chloro-1-methylpyridinium iodide, an alkaline substance and an organic solvent
- -
-
Paragraph 0037-0046; 0050-0053
(2019/03/28)
-
- Br?nsted Base Assisted Photoredox Catalysis: Proton Coupled Electron Transfer for Remote C?C Bond Formation via Amidyl Radicals
-
The synthesis of alkyne- and alkene-decorated lactams has been achieved through a photoredox-initiated radical cascade reaction. The developed Br?nsted base assisted, photoredox-catalyzed, intramolecular 5-exo-trig cyclization/intermolecular radical addit
- Jia, Jiaqi,Ho, Yee Ann,Bülow, Raoul F.,Rueping, Magnus
-
supporting information
p. 14054 - 14058
(2018/09/14)
-
- Regiodivergent Rhodium(I)-Catalyzed Azide-Alkyne Cycloaddition (RhAAC) to Access Either Fully Substituted Sulfonyl-1,2,3-triazoles under Mild Conditions
-
A regiodivergent Rh(I)-catalyzed azide-alkyne cycloaddition (RhAAC) was developed for the synthesis of both fully substituted 4-sulfonyl-1,2,3-triazoles and 5-sulfonyl-1,2,3-triazoles in high regioselectivities and yields under mild conditions in one step
- Song, Wangze,Zheng, Nan,Li, Ming,Dong, Kun,Li, Junhao,Ullah, Karim,Zheng, Yubin
-
supporting information
p. 6705 - 6709
(2018/11/02)
-
- Synthetic method of alkynyl sulfone derivative
-
The invention provides a synthetic method of an alkynyl sulfone derivative. The method is characterized in that alkynyl sulfone derivative is obtained through a reaction of alkynyl bromide and organic sodium sulfinate in the presence of an organic solvent and a strong acid used as a catalyst; and the organic solvent is one or more of toluene, chloroform, 1,2-dichloroethane, 1,4-dioxane and tetrahydrofuran. The method has the advantages of no use of complex reaction substrates or strong oxidants, simple and easily available reaction raw materials, safety and simplicity in reaction operation, environmentally-friendly reaction process, good substrate applicability, good function group tolerance, and high separation yield under preferable conditions and the alkynyl sulfone derivative synthesized through the method widely exists in natural products and medicine molecules, and also can be used as a very effective alkynylation reagent.
- -
-
Paragraph 0022; 0023; 0024; 0025; 0026; 0027-0029; 0030
(2017/05/13)
-
- Direct cross-coupling of aryl alkynyliodines with arylsulfinic acids leading to alkynyl sulfones under catalyst-free conditions
-
A facile and efficient one-pot method has been developed for the construction of alkynyl sulfones via direct cross-coupling reaction of aryl alkynyliodines and arylsulfinic acids. The present transformation could be accomplished under catalyst- and additive-free conditions, providing a series of alkynyl sulfones in moderate to good yields with favorable functional group tolerance.
- Wang, Leilei,Wei, Wei,Yang, Daoshan,Cui, Huanhuan,Yue, Huilan,Wang, Hua
-
supporting information
p. 4799 - 4802
(2017/11/27)
-
- Radical C(sp3)-H alkenylation, alkynylation and allylation of ethers and amides enabled by photocatalysis
-
An efficient radical addition/elimination reaction that enables selective incorporation of alkenyl, alkynyl and allyl functional groups into the C(sp3)-H bond under green reaction conditions is developed. The process is based on the catalytic formation of α-alkoxyl/α-amidyl radicals via the homolytic activation of the C(sp3)-H bond of ethers/amides with a catalytic amount of diarylketone in the presence of a household fluorescent light bulb. This simple reaction protocol features good functional group tolerance, scalability, convenient reagents and operating systems. Synthetic application of the method has been demonstrated via the preparation of natural products and different valuable synthones.
- Paul, Subhasis,Guin, Joyram
-
supporting information
p. 2530 - 2534
(2017/07/17)
-
- Acid-mediated sulfonylation of arylethynylene bromides with sodium arylsulfinates: Synthesis of (: E)-1,2-bis(arylsulfonyl)ethylenes and arylacetylenic sulfones
-
A solvent-dependent sulfonylation of arylethynylene bromides with sodium arylsulfinates has been developed. The (E)-1,2-bis(arylsulfonyl)ethylenes were formed in DMSO, while the arylacetylenic sulfones were obtained in toluene. Utilizing simple and readily available starting materials, the sulfonylation products were generated with good selectivities and yields without the need for a metal catalyst or oxidant.
- Dai, Chenshu,Wang, Junqi,Deng, Siqi,Zhou, Candong,Zhang, Wenhe,Zhu, Qiuhua,Tang, Xiaodong
-
p. 36112 - 36116
(2017/07/27)
-
- Zirconocene Catalysis in Organoaluminum Synthesis of 1-Alkenyl Sulfones and Sulfides
-
The Cp2ZrCl2-catalyzed methylalumination of 1-alkynyl sulfones and 1-alkynyl sulfides with Me3Al, followed by deuterolysis or hydrolysis, affords the corresponding β,β-disubstituted 1-alkenyl sulfones and 1-alkenyl sulfides in high yields. S-Methyl methanethiosulfonate is shown to be a convenient and efficient sulfanylating agent for 1-alkenylaluminum derivatives.
- Kadikova, Rita N.,Ramazanov, Ilfir R.,Vyatkin, Alexey V.,Dzhemilev, Usein M.
-
supporting information
p. 1889 - 1897
(2017/04/06)
-
- Visible-light photoredox synthesis of internal alkynes containing quaternary carbons
-
A novel and efficient visible-light photoredox method for the synthesis of internal alkynes containing quaternary carbons has been developed via coupling reactions of N-phthalimidoyl oxalates of tert-alcohols with 1-(2-(arylsulfonyl)ethynyl)benzenes. The reactions proceeded well at room temperature with good functional group tolerability.
- Gao, Chang,Li, Jingjing,Yu, Jipan,Yang, Haijun,Fu, Hua
-
supporting information
p. 7292 - 7294
(2016/06/09)
-
- Consecutive visible-light photoredox decarboxylative couplings of adipic acid active esters with alkynyl sulfones leading to cyclic compounds
-
Novel and efficient consecutive photoredox decarboxylative couplings of adipic acid active esters (bis(1,3-dioxoisoindolin-2-yl)-substituted hexanedioates) with substituted 1-(2-arylethynylsulfonyl)benzenes have been developed under visible-light photocatalysis. The successive photoredox decarboxylative C-C bond formation at room temperature afforded the corresponding cyclic compounds in good yields with tolerance of some functional groups.
- Li, Jingjing,Tian, Hua,Jiang, Min,Yang, Haijun,Zhao, Yufen,Fu, Hua
-
supporting information
p. 8862 - 8864
(2016/07/22)
-
- Iodine-catalyzed Sulfonylation of Arylacetylenic Acids and Arylacetylenes with Sodium Sulfinates: Synthesis of Arylacetylenic Sulfones
-
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
-
p. 2744 - 2752
(2016/04/26)
-
- Electrosynthesis of (E)-Vinyl Sulfones Directly from Cinnamic Acids and Sodium Sulfinates via Decarboxylative Sulfono Functionalization
-
A variety of (E)-vinyl sulfones were constructed directly from cinnamic acids and sodium sulfinates with high regioselectivity at room temperature by virtue of an electrocatalytic oxidation. A radical intermediate was detected, and the corresponding mecha
- Qian, Peng,Bi, Meixiang,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
-
p. 4876 - 4882
(2016/07/06)
-
- Direct difunctionalization of alkynes with sulfinic acids and molecular iodine: A simple and convenient approach to (E)-β-iodovinyl sulfones
-
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
-
p. 4416 - 4419
(2015/02/19)
-
- Recognition characteristics of an adaptive vesicular assembly of amphiphilic baskets for selective detection and mitigation of toxic nerve agents
-
We used isothermal titration calorimetry to investigate the affinity of basket 1 (470 ?3) for trapping variously sized and shaped organophosphonates (OPs) 2-12 (137-244 ?3) in water at 298.0 K. The encapsulation is, in each case, dri
- Chen, Shigui,Ruan, Yian,Brown, Jason D.,Hadad, Christopher M.,Badji, Jovica D.
-
supporting information
p. 17337 - 17342
(2015/02/02)
-
- Photoredox α-vinylation of α-amino acids and N -aryl amines
-
A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.
- Noble, Adam,MacMillan, David W. C.
-
supporting information
p. 11602 - 11605
(2014/11/08)
-
- Improving alkynyl(aryl)iodonium salts: 2-anisyl as a superior aryl group
-
The majority of alkynyl(aryl)iodonium salts reported in the literature are derived from iodobenzene. This article describes the effects of varying this iodoarene building block on the synthesis, reactivity and stability of these salts. Two procedures to synthesize a variety of known and novel alkynyl(aryl)iodonium tosylates directly from the iodoarene are reported. In the reactions of these salts, those derived from 2-iodoanisole gave superior results than the others tested in every reaction. Isothermal microcalorimetry indicated that these novel salts were significantly more stable and less prone to decomposition than all of the other derivatives. This journal is the Partner Organisations 2014.
- Hamnett, David J.,Moran, Wesley J.
-
p. 4156 - 4162
(2014/06/10)
-
- Silylboranes as new sources of silyl radicals for chain-transfer reactions
-
Various silylboranes, which were outfitted with a catecholborane moiety at one end and a (Me3Si)3Si moiety at the other end of a carbon chain, were prepared through the hydroboration of the corresponding unsaturated silanes. The C-ce
- Rouquet, Guy,Robert, Frederic,Mereau, Raphaal,Castet, Frederic,Renaud, Philippe,Landais, Yannick
-
supporting information; experimental part
p. 940 - 950
(2012/02/16)
-
- Oxidation of organic sulfides and disulfides with a tert-butyl hydroperoxide-aluminum tri-tert-butoxide system
-
Methyl phenylethynyl and phenyl phenylethynyl sulfides are selectively converted into methyl phenylethynyl and phenyl phenylethynyl sulfones, respectively, under the action of system tert-butyl hydroperoxide-aluminum tri-tert-butoxide in benzene at 20 °C. The analogous oxidation of diphenyl disulfide results in S-phenyl benzenethiosulfonate.
- Zaburdaeva,Dodonov
-
experimental part
p. 185 - 187
(2011/09/12)
-
- Ruthenium-catalyzed [2+2] cycloadditions of alkynyl sulfides and alkynyl sulfones
-
Ruthenium-catalyzed [2+2] cycloadditions of bicyclic alkenes with alkynyl sulfides and alkynyl sulfones were investigated. The sulfide and sulfone moieties were found to be compatible with the Ru-catalyzed cycloadditions, giving the corresponding cyclobut
- Riddell, Nicole,Tam, William
-
p. 1934 - 1937
(2007/10/03)
-
- Studies on hydrozirconation of 1-alkynyl sulfoxides or sulfones and the application for the synthesis of stereodefined vinyl sulfoxides or sulfones
-
The hydrozirconation reaction of 1-alkynyl sulfoxides or sulfones with CP2Zr(H)Cl in THF at room temperature predominantly gave Z-β-zirconated vinyl sulfoxides or sulfones with excellent regioselectivity. Compared with 1-alkynyl sulfoxides, the hydrozirconation reaction of 1-alkynyl sulfones exhibits great synthetic potential, leading to the efficient preparation of Z-β-halovinyl sulfones, Z-β-sulfonyl α,β-unsaturated ketones, and Z-β-alkynyl vinyl sulfones. Although the reaction mechanisms are still not clear, the neighboring group participation of the sulfinyl or sulfonyl group may be playing an important role in this unique hydrozirconation reaction.
- Huang, Xian,Duan, Dehui,Zheng, Weixin
-
p. 1958 - 1963
(2007/10/03)
-
- Polystyrene-supported selenosulfonates: Efficient reagents for the synthesis of acetylenic sulfones
-
Two novel polystyrene-supported selenosulfonate reagents have been developed for AIBN-catalyzed addition to acetylenes and have been used for the synthesis of acetylenic sulfones.
- Qian, Hao,Huang, Xian
-
p. 1059 - 1061
(2007/10/03)
-
- CAN mediated reaction of aryl sulfinates with alkenes and alkynes: Synthesis of vinyl sulfones, β-iodovinyl sulfones and acetylenic sulfones
-
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
-
p. 2259 - 2265
(2007/10/03)
-
- Preparation of resin-bound alkynyl iodonium salts and their application in organic synthesis as alkynyl transfer reagents
-
We have synthesized polymer-supported alkynylphenyl iodonium salts. They served as effective alkynyl transfer reagents for the preparation of acetylenic sulfones; the by-product, polymer supported (4-iodostyrene), could be reactivated for reuse numerous t
- Huang, Xian,Zhu, Qing
-
p. 6373 - 6375
(2007/10/03)
-
- Copper-mediated nucleophilic displacement reactions of 1-haloalkynes. Halogen-halogen exchange and sulfonylation
-
Some copper(I) and (II) compounds have been found to act as efficient reagents for the nucleophilic displacement of 1-haloalkynes. Copper(I) iodide smoothly transforms 1-bromoalkynes (2) into 1-iodoalkynes (1) which, on further treatment with copper(II) bis(arenesulfinate), are readily converted to the corresponding alkynyl aryl sulfones (4). The kinetic data of the halogen exchange between (4-chlorophenyl)ethynyl bromide (2d) and CuI have shown that the reaction is linearly dependent on the concentrations of both compounds. A mechanistic pathway involving the single electron transfer between 1-haloalkynes and copper(I) salt has been proposed for the present copper-assisted halogen exchange reaction at acetylenic carbon atom.
- Abe, Hajime,Suzuki, Hitomi
-
p. 787 - 798
(2007/10/03)
-
- Chemoselective electrooxidation of (E)1-phenyl-2-(phenylthio)ethylene and 1-phenyl-2-(phenylthio) acetylene
-
Electrooxidation of (E)-1-phenyl-2-(phenylthio)ethylene and 1-phenyl-2- (phenylthio)acetylene on glassy carbon electrode in acetonitrile medium results in the formation of the corresponding sulphones chemoselectively leaving the unsaturated linkages intac
- Ramalingam,Perumal,Selvaraj,Sivasubramanian
-
p. 466 - 469
(2007/10/03)
-
- Phenacyl aryl sulfones as synthons for 1,2,3-selenadiazoles and thiadiazoles
-
4-Aryl-5-arylsulfonyl-1,2,3-selenadiazole 4a-1 and 4-aryl-5-arylsulfonyl-1,2,3-thiadiazole 5a-1 have been prepared from phenacyl aryl sulfones (2a-1). The 4 on pyrolysis yields 1-arylsulfonyl-2-aryl acetylenes 6a-1.
- Padmavathi, V.,Reddy, A. V. Bhaskar,Reddy, A. Somasekhar,Reddy, D. Bhaskar
-
p. 1062 - 1065
(2007/10/03)
-
- A new straightforward synthesis of alkynyl sulfones via the sonochemical coupling between alkynyl halides and copper sulfinates
-
Alkynyl aryl sulfones 2 were easily obtained in moderate to good yields by treating alkynyl iodides 1 with copper arenesulfinates in a tetrahydrofuran suspension under ultrasonic irradiation.
- Suzuki, Hitomi,Abe, Hajime
-
p. 3717 - 3720
(2007/10/03)
-
- Nickel(0)-induced geminal bond cleavages leading to carbon-carbon double bonds: Intermediacy of nickel(0)-carbene complexes as a unifying hypothesis
-
The possibility of effecting geminal bond cleavages of organic monomers with nickel(0) complexes to achieve olefinic dimers has been investigated both in stoichiometric reactions between monomers of the type R2CE2 and R2C=E and the complexes (Cod)2Ni, (Et3P)4Ni and (Bpy)(Cod)Ni and in nickel(0)-catalytic α-elimination reactions of α-lithioorganic sulfones, RR′C(Li)(SO2R″). Substrates for the stoichiometric geminal bond cleavages comprised geminal dihalides, aminomethyl sulfides, cyclopropenes, thioketones and ketones. Reductive dimerization to the olefin or its hydroxy derivatives was found to occur to a varying degree in most cases, including the catalytic decomposition of the α-lithioorganic sulfones. Accordingly, this method offers considerable promise in organic synthesis. A gamut of known nickel(0) chemistry, results of chemical-trapping and spectroscopic evidence are marshaled in support of the proposal that such geminal bond cleavages and reductive coupling processes most likely proceed via nickel(0)-carbene intermediates of the type R2C=Ni · Ln.
- Eisch, John J.,Qian, Yun,Singh, Mona
-
p. 207 - 217
(2007/10/03)
-
- Hypervalent iodine in synthesis: 9. A new, effective synthesis of acetylenic sulfones
-
Alkynylphenyliodonium salts can easily react with sodium sulfinates under PTC conditions at room temperature to afford a convenient, effective method for the preparation of acetylenic sulfones.
- Liu,Chen
-
p. 1997 - 2003
(2007/10/02)
-
- Approaches to 2,6-Diaryl-3,7-DioxabicycloOctane Lignans via Asymmetric Synthesis of Dihydro- and Tetrahydro-furan Derivatives
-
Cyclisation of chiral non-racemic phenylsulphonylvinyl epoxy ethers, produced using the Sharpless epoxidation reaction, has been used to prepare a series of enantiomerically enriched 2-aryl-4-(α-hydroxybenzyl)-4,5-dihydrofuran derivatives.Reduction of these compounds using triethylsilane and BF3-diethyl ether gave the corresponding tetrahydrofuran derivatives stereoselectively.Attempts to convert either the dihydro- or tetrahydro-furan derivatives into lignans belonging to the 2,6-diaryl-3,7-dioxabicyclooctane series so far proved unsuccessful.
- Pelter, Andrew,Ward, Robert S.,Little, Gillian M.
-
p. 2775 - 2790
(2007/10/02)
-
- Dipolar cycloaddition reaction of diazoalkanes with trimethylsilyl substituted alkynes. Steric control of regiochemistry by the trimethylsilyl group
-
A study of the cycloaddition behavior of several trimethylsilyl substituted alkynes with 2-diazopropane and diazomethane has been carried out. Aryl or alkyl ethynyl sulfones react to give 5-sulfonyl substituted 3H-pyrazoles which extrude nitrogen on photo
- Padwa, Albert,Wannamaker, M. Woods
-
p. 1145 - 1162
(2007/10/02)
-
- One-pot Synthesis of Acetylenic Sulfones from Chloro(phenylsulfonyl)methanephosphonate
-
Acetylenic sulfones are obtained in one-pot by the reaction of chloro(phenylsulfonyl)methanephosphonate with aromatic aldehydes in the presence of excess base.
- Lee, Jae Wook,Kim, Taek Hyeon,Oh, Dong Young
-
p. 2633 - 2638
(2007/10/02)
-
- Reactions of Alkylmercurials with Heteroatom-Centered Acceptor Radicals
-
The relative reactivities of alkylmercury halides toward PhS., PhSe., or I. decrease drastically from R = tert-butyl to R = sec-alkyl to R = n-butyl, indicative that R. is formed in the rate-determining step in the attack of these radicals upon RHgCl.The alkyl radicals thus formed will enter into chain reactions in which a heteroatom-centered radical (A.) is regenerated from substrates such as RS-SR, ArSe-SeAr, ArTe-TeAr, PhSe-SO2Ar, Cl-SO2Ph; ZCH=CHA (A = Cl, I, SPh, SO2Ph); or PhCCHA (A = I, SPh, SO2Ph). β-Styrenyl (PhCH=CHA, Ph2C=CHA) and β-phenethynyl (PhCCA) systems with A = I, Br, SO2Ph also enter into chain reactions with mercury(II) salts with the ligands PhS, PhSe, PhSO2, or (EtO)2PO.The relative reactivities of a series of reagents toward t-Bu. and of PhCH=CHA, Ph2C=CHA, and PhCCA toward c-C6H11. are reported as well as the regioselectivity of t-Bu. attack observed for 1,2-disubstituted ethylenes (ZCH=CHA) with Z and A from the group Ph, Cl, Br, I, SO2Ph, SPh, Bu3Sn.Reactions of (E)- and (Z)-PhCH=CHI or MeO2CCH=CHI with t-Bu. or c-C6H11. occurred in a regioselective and stereospecific (retention) manner.Reactions of (E)- and (Z)-ClCH=CHCl occurred in a nonstereospecific manner in which the E/Z product ratio increased with the bulk of the attacking radical.A similar effect on the E/Z product ratios was observed for (Z)-MeO2CCH=CHCl.
- Russell, Glen A.,Ngoviwatchai, Preecha,Tashtoush, Hasan I.,Pla-Dalmau, Anna,Khanna, Rajive K.
-
p. 3530 - 3538
(2007/10/02)
-
- Alkynes from 5-Aminoisoxazoles
-
Diazotization of 5-aminoisoxazoles that bear at least one electron-withdrawing group by reaction with sodium nitrite in AcOH-H2O affords substituted acetylenes.A reaction path is proposed.
- Beccalli, Egle M.,Manfredi, Amedea,Marchesini, Alessandro
-
p. 2372 - 2375
(2007/10/02)
-
- Process for the production of bromo substituted tetrahydrofuran sulfones
-
A process for the manufacture of β-bromoalkylsulfones and β-bromoalkenylsulfones by addition reaction of sulfonic acid bromides with olefins or acetylenes in the presence of hydroperoxide and, optionally, of metal salts. Starting materials for further syn
- -
-
-