54826-51-6Relevant academic research and scientific papers
Dihalogenation of Alkenes Using Combinations of N-Halosuccinimides and Alkali Metal Halides
Barrio, Pablo,García-Pedrero, Olaya,López-Matanza, Pablo,Rodríguez, Félix,Rubio-Presa, Rubén
supporting information, p. 4762 - 4766 (2021/09/10)
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
Synthetic method of beta-ethyl iodoacetate compound
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Paragraph 0028; 0029; 0031; 0032; 0034; 0035; 0037; 0038, (2019/01/23)
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
Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes
Hokamp, Tobias,Storm, Alena Therese,Yusubov, Mekhman,Wirth, Thomas
supporting information, p. 415 - 418 (2017/10/30)
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.
Regio- and stereoselective co-iodination of olefins using NH4I and Oxone
Durgaiah, Chevella,Naresh, Mameda,Arun Kumar, Macharla,Swamy, Peraka,Reddy, Marri Mahender,Srujana, Kodumuri,Narender, Nama
supporting information, p. 1133 - 1144 (2016/07/22)
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.
Regioselective vicinal functionalization of unactivated alkenes with sulfonium iodate(i) reagents under metal-free conditions
Rao, Dodla S.,Reddy, Thurpu R.,Babachary, Kalvacherla,Kashyap, Sudhir
, p. 7529 - 7543 (2016/08/16)
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.
PIDA-I2 mediated direct vicinal difunctionalization of olefins: Iodoazidation, iodoetherification and iodoacyloxylation
Achar, Tapas Kumar,Maiti, Saikat,Mal, Prasenjit
, p. 4654 - 4663 (2016/06/09)
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.
PROCESS FOR THE PREPARATION OF N-IODOAMIDES
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Paragraph 00267-00268, (2015/05/26)
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.
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
Chakraborty, Nirnita,Santra, Sougata,Kundu, Shrishnu Kumar,Hajra, Alakananda,Zyryanov, Grigory V.,Majee, Adinath
, p. 56780 - 56788 (2015/07/15)
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.
Hypoiodite-catalyzed regioselective oxidation of alkenes: An expeditious access to aldehydes in aqueous micellar media
Swamy, Peraka,Reddy, Marri Mahender,Naresh, Mameda,Kumar, Macharla Arun,Srujana, Kodumuri,Durgaiah, Chevella,Narender, Nama
supporting information, p. 1125 - 1130 (2015/04/22)
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.
Dichloroiodoisocyanuric acid: A new reagent for regioselective coiodination of alkenes and iodination of activated arenes
Da Silva Ribeiro, Rodrigo,Esteves, Pierre M.,De Mattos, Marcio C.S.
experimental part, p. 228 - 235 (2012/05/05)
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.
