54826-41-4Relevant academic research and scientific papers
Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons
Zhang, Zhenhua,Górski, Bartosz,Leonori, Daniele
supporting information, p. 1986 - 1992 (2022/02/01)
We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel
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.
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.
m-Iodosylbenzoic acid, a tagged hypervalent iodine reagent for the iodo-functionalization of alkenes and alkynes
Yusubov, Mekhman S.,Yusubova, Roza Ya.,Kirschning, Andreas,Park, Joo Yeon,Chi, Ki-Whan
, p. 1506 - 1509 (2008/09/19)
An efficient and facile method for the iodo-functionalization of alkenes 5 and alkynes 6 by using recyclable m-iodosylbenzoic acid (2) was developed. The final products can be easily isolated without any chromatographic purification by simple treatment of the crude mixture with an anionic exchange resin. Unreacted m-iodosylbenzoic acid and reduced m-iodobenzoic acid are effectively recovered from the resin by acidification with hydrochloric acid.
Triiodoisocyanuric acid: a new and convenient reagent for regioselective coiodination of alkenes and enolethers with oxygenated nucleophiles
Ribeiro, Rodrigo da S.,Esteves, Pierre M.,de Mattos, Marcio C.S.
, p. 8747 - 8751 (2008/03/18)
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%).
RETRACTED ARTICLE: Regioselective 1,2-hydroxy and methoxy iodination of alkenes by molecular iodine and aqueous hydrogen peroxide
Raju, B. Rama,Kumar, E.K. Pramod,Saikia, Anil K.
, p. 1997 - 2001 (2007/10/03)
Treatment of an alkene with iodine and aqueous hydrogen peroxide (30%) in acetonitrile gives the corresponding hydroxyiodoalkane regioselectively in high yield. On the other hand the same reaction in methanol gives methoxyiodoalkanes in excellent yield.
Trans dialkoxylation of cyclic alkenes: A Prevost-type reaction
Schauble, J. Herman,Trauffer, Edward A.,Deshpande, Prashant P.,Evans, Robert D.
, p. 1333 - 1339 (2007/10/03)
Reaction of anhydrous silver perchlorate, sym-collidine, and iodine (2:1:1 molar ratio) with cyclic alkenes and an excess of an alcohol in CH 2Cl2 affords trans-1,2-dialkoxycycloalkanes in high yields and purity. The reaction occurs via initial formation of the trans-iodoethers, which undergo Ag-assisted iodide abstraction to give the trans-diethers. Georg Thieme Verlag Stuttgart.
(Dichloroiodo)benzene - An Easily Available Reagent for Chloro- and Iodoalkoxylation, Iodohydroxylation, and Iodochlorination of Alkenes
Yusubov,Yusubova,Filimonov,Chi, Ki-Whan
, p. 443 - 450 (2007/10/03)
A convenient synthesis of vicinal methoxychlorides, methoxyiodides, iodhydrines and iodochloride from alkenes using PhICl2/CH 3OH, I2/ PhICl2/CH3OH, I 2/PhICl2/CH3CN/H2O and I 2/PhICl2/CH2Cl2 is described.
Regioselective 1,2-alkoxy, hydroxy, and acetoxy iodination of alkenes with I2 catalyzed by Ce(SO3CF3)4
Iranpoor, Nasser,Shekarriz, Marzieh
, p. 5209 - 5211 (2007/10/03)
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.
N-iodosaccharin - A new reagent for iodination of alkenes and activated aromatics
Dolenc, Darko
, p. 544 - 546 (2007/10/03)
A mild and efficient iodination reagent, N-iodosaccharin was prepared. Iodination of activated aromatics and alkenes with the reagent takes place fast and under very mild conditions, without the aid of strong acids or heavy metals. The reagent does not affect oxidizable groups, such as hydroxyl or aldehyde.
