- Dihalogenation of Alkenes Using Combinations of N-Halosuccinimides and Alkali Metal Halides
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A simple, efficient and eco-friendly method for the vicinal dihalogenation of alkenes is described. The reaction is performed with a combination of a N-halosuccinimide and an alkali metal halide using environmentally benign solvents such as acetic acid an
- Barrio, Pablo,García-Pedrero, Olaya,López-Matanza, Pablo,Rodríguez, Félix,Rubio-Presa, Rubén
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supporting information
p. 4762 - 4766
(2021/09/10)
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- Synthetic method of beta-ethyl iodoacetate compound
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The invention discloses a synthetic method of a beta-ethyl iodoacetate compound. The synthetic method of the beta-ethyl iodoacetate compound comprises the following steps: taking a styrene compound shown in formula I as a raw material, mixing the styrene
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Paragraph 0028; 0029; 0031; 0032; 0034; 0035; 0037; 0038
(2019/01/23)
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- Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes
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A novel and inexpensive, environmentally friendly method for the preparation of iodine monoacetate is presented using iodine and Oxone in acetic acid/acetic anhydride. The reagent is used in a highly efficient approach for the regio- and diastereoselective iodo-acetoxylation of alkenes and alkynes in a simple one-pot process.
- Hokamp, Tobias,Storm, Alena Therese,Yusubov, Mekhman,Wirth, Thomas
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supporting information
p. 415 - 418
(2017/10/30)
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- Regio- and stereoselective co-iodination of olefins using NH4I and Oxone
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A simple, efficient, and environmentally benign protocol for the synthesis of vicinal iodohydrins and iodoesters from olefins using NH4I and Oxone in CH3CN/H2O (1:1) and dimethylformamide (DMF) / dimethylacetamide (DMA), respectively, without employing a catalyst at room temperature is described. Regio- and stereoselective iodohydroxylation and iodoesterification of various olefins with anti fashion, following Markonikov’s rule, was achieved and the corresponding products were obtained in good to excellent yields. In addition, 1,2-disubstituted olefins afforded excellent diastereoselectivity.
- Durgaiah, Chevella,Naresh, Mameda,Arun Kumar, Macharla,Swamy, Peraka,Reddy, Marri Mahender,Srujana, Kodumuri,Narender, Nama
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supporting information
p. 1133 - 1144
(2016/07/22)
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- Regioselective vicinal functionalization of unactivated alkenes with sulfonium iodate(i) reagents under metal-free conditions
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Metal-free, molecular iodine-free direct 1,2-difunctionalization of unactivated alkenes has been reported. The sulfonium iodate(i) reagent efficiently promoted the intermolecular vicinal iodo-functionalization of a diverse range of olefins in a stereo and regioselective manner. This method enables the divergent and straightforward preparation of synthetically useful functionalities; β-iodocarboxylates, β-iodohydrins, and β-iodoethers in a one-step process. Further interconversion of iodo-functionalized derivatives allows easy access to valuable synthetic intermediates en route to biologically active molecules.
- Rao, Dodla S.,Reddy, Thurpu R.,Babachary, Kalvacherla,Kashyap, Sudhir
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p. 7529 - 7543
(2016/08/16)
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- PIDA-I2 mediated direct vicinal difunctionalization of olefins: Iodoazidation, iodoetherification and iodoacyloxylation
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Iodinium cation (I+ or IOAc) was produced from the combination of phenyliodine diacetate (PIDA) and iodine. I+ facilitated the direct vicinal difunctionalization of olefins to α-azido, α-trideuteriomethoxy, α-2,2,2-trifluoroethoxy and α-acyloxy alkyl iodides via cation-π interaction at room temperature and under transition-metal free conditions.
- Achar, Tapas Kumar,Maiti, Saikat,Mal, Prasenjit
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p. 4654 - 4663
(2016/06/09)
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- PROCESS FOR THE PREPARATION OF N-IODOAMIDES
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The present invention provides new stable crystalline N-iodoamides - 1-iodo- 3,5,5-trimethylhydantoin (1-ITMH) and 3-iodo-4,4-dimethyl-2-oxazolidinone (IDMO). The present invention further provides a process for the preparation of organic iodides using N-iodoamides of this invention and recovery of the amide co-products from waste water.
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Paragraph 00267-00268
(2015/05/26)
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- Combination of NH2OH·HCl and NaIO4: an effective reagent for molecular iodine-free regioselective 1,2-difunctionalization of olefins and easy access of terminal acetals
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We have demonstrated a new application of our oxidizing reagent, a combination of NH2OH·HCl and NaIO4, in the first generalized regioselective 1,2-difunctionalization of olefins. It is a general method for the preparation of β-iodo-β′-hydroxy ethers, β-iodo ethers, β-iodohydrin, and β-iodo acetoxy compounds using different reaction media. The reactions are highly regioselective, always affording Markovnikov's type addition products. The methodology is also applicable for the easy access of terminal acetals. Molecular iodine-free synthesis, room temperature reaction conditions, high yields, use of less expensive reagents, mild reaction conditions, broad applicability of nucleophiles, and applicability for gram-scale synthesis are the notable advantages of this present protocol.
- Chakraborty, Nirnita,Santra, Sougata,Kundu, Shrishnu Kumar,Hajra, Alakananda,Zyryanov, Grigory V.,Majee, Adinath
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p. 56780 - 56788
(2015/07/15)
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- Hypoiodite-catalyzed regioselective oxidation of alkenes: An expeditious access to aldehydes in aqueous micellar media
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A highly anti-Markovnikov selective oxidation of alkenes based on in situ generated hypoiodite catalysis in aqueous micellar media under mild conditions has been described. This novel catalytic system realizes an efficient synthesis of aldehydes from alkenes in an economically viable and environmentally safe fashion. The preliminary mechanistic studies suggest that the reaction proceeds via tandem iodofunctionalization/1,2-aryl or alkyl migration. The scope and limitations of this tandem process are demonstrated with various mono- and disubstituted (terminal and internal) olefins.
- Swamy, Peraka,Reddy, Marri Mahender,Naresh, Mameda,Kumar, Macharla Arun,Srujana, Kodumuri,Durgaiah, Chevella,Narender, Nama
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supporting information
p. 1125 - 1130
(2015/04/22)
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- Dichloroiodoisocyanuric acid: A new reagent for regioselective coiodination of alkenes and iodination of activated arenes
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Dichloroiodoisocyanuric acid was prepared in 93% by heating trichloroisocyanuric acid with 1.05 mol equiv. of iodine. This new reagent is very efficient for regioselective electrophilic iodination of activated arenes. Alkenes react with dichloroiodoisocyanuric acid in the presence of oxygenated nucleophiles (water, alcohols, and acetic acid), leading to the corresponding iodohydrins, β-iodoethers and β-iodoacetates with reaction times of less than one minute and with a high degree of regioselectivity. Enol ethers resulted in the regioselective formation of the corresponding iodine-dialkylacetals. Experimental results and DFT calculations showed that dichoroiodoisocyanuric acid is more reactive with unsaturated systems than triiodoisocyanuric acid.
- Da Silva Ribeiro, Rodrigo,Esteves, Pierre M.,De Mattos, Marcio C.S.
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experimental part
p. 228 - 235
(2012/05/05)
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- Addition of halide to π-bond directly from aqueous NaX solution: A general strategy for installation of two different functional groups
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Activation of π-bond with organic Lewis acid and cationic surfactant mediated direct transfer of halides to alkyne and alkene are demonstrated to afford α,α-dihaloketones and other valuable synthons with outstanding selectivities.
- Pandit, Palash,Gayen, Krishnanka S.,Khamarui, Saikat,Chatterjee, Nirbhik,Maiti, Dilip K.
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supporting information; experimental part
p. 6933 - 6935
(2011/08/06)
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- Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents
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A comparative evaluation was made on the syntheses of vicinal halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br-/BrO3- and I-/IO3- reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br-/BrO3- and I-/IO3-, respectively. Of the two reagents, I-/IO3- was established to be the preferred reagent for vicinal functionalization of linear alkenes and also for halo acetate preparation. However, only Br-/BrO3- was effective for vicinal functionalization of trans-stilbene and chalcones.
- Agrawal, Manoj K.,Adimurthy, Subbarayappa,Ganguly, Bishwajit,Ghosh, Pushpito K.
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experimental part
p. 2791 - 2797
(2009/08/08)
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- PhI(OAc)2/I2 induced aziridination of alkenes with TsNH2 under mild conditions
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The aziridination of alkenes with the direct use of p-toluenesulfonamide (TsNH2) was achieved by using PhI(OAc)2 and I2 under mild conditions. The reaction affords aziridines in moderate to good yields, and offers good man
- Fan, Renhua,Pu, Dongming,Gan, Jianhong,Wang, Bing
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p. 4925 - 4928
(2008/09/21)
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- A new procedure for highly regio- and stereoselective iodoacetoxylation of protected glycals and α-1,2-cyclopropanated sugars
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Protected glycals and -1,2-cyclopropanated sugars were converted in high yields and selectivities in less than 2h at low temperatures to 2-deoxy-2-iodoglycosyl acetates or novel 2-deoxy-2-iodomethylglycosyl acetates using the simple, inexpensive reagent m
- Gammon, David W.,Kinfe, Henok H.,De Vos, Dirk E.,Jacobs, Pierre A.,Sels, Bert F.
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p. 141 - 157
(2008/02/11)
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- Triiodoisocyanuric acid: a new and convenient reagent for regioselective coiodination of alkenes and enolethers with oxygenated nucleophiles
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The reaction of triiodoisocyanuric acid (prepared from I2 and trichloroisocyanuric acid in 90% yield) with alkenes in the presence of oxygenated nucleophilic solvents (alcohols, AcOH and H2O) led to the corresponding β-iodoethers, β-iodoacetates and iodohydrins, in 66-98% isolated yield. Enolethers reacted with triiodoisocyanuric acid in MeOH to produce dialkylacetals (70-83%).
- Ribeiro, Rodrigo da S.,Esteves, Pierre M.,de Mattos, Marcio C.S.
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p. 8747 - 8751
(2008/03/18)
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- Fe2(SO4)3-mediated coiodination of alkenes with acetic acid: A convenient and regioselective eco-friendly preparation of β-iodoacetates
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The reaction of alkenes with I2 and Fe2(SO 4)3 in acetic acid at room temperature produced the corresponding β-iodoacetates in 79-92% isolated yields and high regioselectivity.
- De Mattos, Marcio C.S.,Sanseverino, Antonio Manzolillo
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p. 638 - 639
(2007/10/03)
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- Preparation of α-iodoacetates from alkenes by Co(OAc)2 catalysed Woodward-Prevost reaction
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Woodward-Prevost reaction of alkenes with iodine and cobalt(II) acetate in acetic acid is reported. The reaction is facile and α-iodoacetates are obtained from both acyclic and cyclic alkenes in high yields within 15-55 min.
- Myint, Yi Yi,Pasha
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p. 590 - 592
(2007/10/03)
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- Synthesis of α-iodoacetates from alkenes by cadmium acetate catalysed Woodward's reaction
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Alkenes on treatment with iodine and cadmium acetate in acetic acid give α-iodoacetates in high yields. The reaction is facile and α-iodoacetates are obtained from both acyclic and cyclic alkenes within 5-30 min.
- Myint, Yi Yi,Pasha
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p. 333 - 335
(2007/10/03)
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- Regioselective 1,2-alkoxy, hydroxy, and acetoxy iodination of alkenes with I2 catalyzed by Ce(SO3CF3)4
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The reaction of alkenes and iodine in water, alcohols and acetic acid is catalyzed with ceric triflate under mild conditions. The corresponding 1,2-alkoxy, acetoxy, and hydroxy iodides are obtained in good yields with easy procedure. (C) 2000 Elsevier Science Ltd.
- Iranpoor, Nasser,Shekarriz, Marzieh
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p. 5209 - 5211
(2007/10/03)
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- New, simple 1,2-iodoacetoxylation of alkenes+
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A general synthetic procedure for the preparation of trans-1,2- iodoacetates in good yields from alkenes by reaction with lead diacetate and iodine is reported.
- Bedekar,Nair,Soman
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p. 2299 - 2305
(2007/10/02)
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- β-Functionalised radicals in organic synthesis: 2-Acyloxyalkyl radicals from 2-acyloxyalkyl iodides by the tin route
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The reaction of iodoesters 1a-c with electrophilic olefins 2a-d and in situ generated tributyltin hydride (from a substoichiometric amount of tributyltin chloride and an excess of sodium borohydride) in the presence of a catalytic amound of AIBN in ethanol at 0 to 20°C yields the expected coupling products 3aa-3cd. Products 4 resulting from an iodine/hydrogen exchange are also obtained as by-products in variable amounts. The stereochemistry of the coupling reaction is studied: starting from trans-2-iodocyclohexyl acetate (1d) and methyl acrylate (2a) a 1/3 mixture of the corresponding cis/trans diastereoisomers is obtained. This result indicates that the corresponding radical coupling is not stereospecific.
- Foubelo, Francisco,Lloret, Francisco,Yus, Miguel
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p. 5131 - 5138
(2007/10/02)
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- An Efficient Method for the Copper(II)-promoted Stereoselective Iodofunctionalization of Alkenes
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A mixture of iodine and CuO*HBF4 reacts stereoselectively with alkenes in the presence of a wide variety of nucleophiles (water, MeOH, HCO2H, AcOH, EtCOOH, NaNO2, KSCN, NaSO2Ar, LiCl, LiBr, NaI, Et3SiH, and MeOPh) to give the corresponding 2-functionalized iodo compounds.A regio chemistry study is also reported.
- Barluenga, Jose,Rodriguez, Miguel A.,Campos, Pedro J.
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p. 2807 - 2809
(2007/10/02)
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- Supported Reagents in Facile and Selective Two-phase Additions to C=C Double Bonds
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Inorganic-solid-supported KSCN, NaN3, and KOAc mixed with iodine and an alkene in CHCl3 gave products by a facile two-phase addition.
- Ando, Takashi,Clark, James H.,Cork, David G.,Fujita, Mitsue,Kimura, Takahide
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p. 1301 - 1302
(2007/10/02)
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