1506-50-9Relevant academic research and scientific papers
Iodosobenzene diacetate-Iodine and IBX-Iodine: Reagent systems for the synthesis of diastereomerically enriched 2-deoxy-2-iodoglycosyl acetates and 2-deoxy-2-iodoglycosyl ortho-iodobenzoates from protected glycals
Saidhareddy, Puli,Ajay, Sama,Shaw, Arun K.
, p. 4407 - 4417 (2017/07/03)
Two efficient, metal free reagent systems, PhI(OAc)2-I2 (method A) and IBX-I2 (method B), for stereoselective synthesis of trans-2-deoxy-2-iodoglycosylacetates and O-iodobenzoates respectively from differently protected glycals have been developed. They are compatible with a variety of protecting groups and various functional groups at 2C-position. Hexose-3,2-enolone 8 is obtained directly from 2-acetoxy glycal 5 by method A. An application to modified method B has been shown by synthesis of a diastereomerically pure α-glycosyl ortho-hexynylbenzoate 12, a glycosyl donor from 3,4,6-tri-O-acetyl-D-glucal in two steps that has been further utilized in the synthesis of glycosides 13–18.
Sulfonium Salts of Iodine(I) Species as Efficient Reagents for the Regioselective Bisfunctionalisation of Glycals and Enol Ethers
Reddy, Thurpu Raghavender,Rao, Dodla Sivanageswara,Babachary, Kalvacherla,Kashyap, Sudhir
, p. 291 - 301 (2016/02/18)
A new sulfonium-salt-based iodine(I) reagent system for the vicinal functionalisation of glycals and enol ethers has been developed. The unprecedented iodine(I) complex, Me3SI(OAc)2, generated in situ from Me3SI and PhI(OAc)2, effectively promoted the one-pot iodocarboxylation using carboxylic acids, and iodoazidation using NaN3 or TMSN3 (trimethylsilyl azide). The scope and generality of the new reagent was probed for a wide range of substrates, including various substituted aromatic carboxylic acids, heterocyclic, alicyclic, and aliphatic carboxylic acids, and amino acids to obtain various functionalised glycoconjugates in high yields (99 %) and with diastereoselectivities up to 100 %. A new sulfonium-salt-based iodine(I) reagent system has been developed for the vicinal functionalisation of glycals and enol ethers. The unprecedented iodine(I) complex generated in situ from Me3SI and PhI(OAc)2 effectively promoted iodocarboxylation and iodoazidation reactions in excellent yields and with diastereoselectivities up to 100 %.
NaIO4-KI-NaN3 as a new reagent system for C-H functionalization in hydrocarbons
Chouthaiwale, Pandurang V.,Suryavanshi, Gurunath,Sudalai, Arumugam
scheme or table, p. 6401 - 6403 (2009/04/06)
The NaIO4-KI-NaN3 combination has been found to be an efficient, reliable, and inexpensive reagent system for mono- and 1,2-difunctionalization of hydrocarbons via C-H bond activation to afford vicinal azido- and acetoxy iodinations of cyclic hydrocarbons.
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%).
Aerobic oxidation of alkenes to esters of vicinal diols with a syn-configuration catalyzed by I2 and the H5PV 2Mo10O40 polyoxometalate
Branytska, Olena,Neumann, Ronny
, p. 2525 - 2527 (2007/10/03)
A new method for the synthesis of vicinal diols from alkenes has been developed. Reaction of molecular iodine in the presence of a polyoxometalate as oxidation catalyst under aerobic conditions in acetic acid solvent leads to the oxidative iodoacetoxylation of an alkene, i.e. formation of a 1,2-iodoacetate. Further in situ substitution of the iodide by water yields the 1,2-diol monoacetate with a predominantly (ca. 4.5:1) cis-configuration. Further esterification under the reaction's acidic conditions leads also to the cis-diacetate. The method may be valuable for the synthesis of cis-vicinal diols without use of toxic osmium catalysts. Georg Thieme Verlag Stuttgart.
A new synthesis of cis-diol from alkene using iodine-ammonium cerium(IV) nitrate
Horiuchi, C. Akira,Dan, Gong,Sakamoto, Masaki,Suda, Kazuhiko,Usui, Shigeru,Sakamoto, Okihiko,Kitoh, Shinya,Watanabe, Satoshi,Utsukihara, Takamitsu,Nozaki, Sukekatsu
, p. 2861 - 2864 (2007/10/03)
The reaction mixtures of 5α-cholest-2-ene with iodine-ammonium cerium(IV) nitrate [CAN(IV)] were converted with potassium hydroxide in methanol-water to give the more hindered 2β,3β-diol in high yield. Cyclohexene and cycloheptene similarly reacted to the corresponding cis-diols in good yield. It was found that this reaction intermediate proceeds to give trans-iodoacetate via trans-iodonitrate. This new synthetic method provided several advantages over the Prevost reaction. Georg Thieme Verlag Stuttgart.
Regioselective synthesis of α-iodoacetates from alkenes/ammonium acetate/I2 by Woodward's reaction
Myint, Yi Yi,Pasha
, p. 4477 - 4482 (2007/10/03)
Regioselective synthesis of α-iodoacetates from alkenes, ammonium acetate, and iodine in acetic acid is reported. The reaction is facile, fast, environmentally, friendly, and cost effective. α-Iodoacetates are obtained from both acyclic and cyclic alkenes
Synthesis of α-iodoacetates from alkenes by cadmium acetate catalysed Woodward's reaction
Myint, Yi Yi,Pasha
, p. 333 - 335 (2007/10/03)
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.
Selective functionalisation of hydrocarbons by nitric acid and aerobic oxidation catalysed by N-hydroxyphthalimide and iodine under mild conditions
Minisci, Francesco,Recupero, Francesco,Gambarotti, Cristian,Punta, Carlo,Paganelli, Roberto
, p. 6919 - 6922 (2007/10/03)
Alkylbenzenes are selectively functionalised to the corresponding acetates by nitric aerobic oxidation catalysed by N-hydroxyphthalimide and iodine. With cyclohexane the oxidation leads to a mixture of cyclohexyl acetate and trans-2-iodocyclohexyl acetate. The mechanism is discussed.
