28141-32-4Relevant academic research and scientific papers
Sonochemical formation of iodohydrin and epoxide from cyclohexene
Fernandes, Vanessa S.,Barboza, Jayne C. S.,Serra, Antonio Aarao
, p. 1433 - 1436 (2007)
Ultrasonic irradiation substantially improves the reaction of cyclohexene with I2 in aqueous dioxane in the presence of Cu(OAc)2 · H2O to generate the expected iodohydrin in high yield. The product undergoes cyclization to the epoxide by biphasic treatment with either Na2CO3 or KOH in a sonication-sensitive step. Copyright Taylor & Francis Group, LLC.
Method for efficiently preparing iodo alcohol
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Paragraph 0013; 0033-0034, (2021/04/17)
The invention discloses a method for efficiently preparing iodohydrin. The preparation method is characterized in that a cyclic ether compound, iodine and hydrogen are used as the reaction raw materials and rhodium and phosphine ligand are used as the catalyst to perform reaction in an organic inert solvent under a positive pressure condition to obtain the target iodohydrin, and the reaction formula of the reaction is as shown in the specification, wherein Z is alkane or aromatic hydrocarbon. The method has the advantages that the iodination of the method can be easily achieved, reaction condition requirements are low, large-scale industrial production can be achieved, and the yield of the iodohydrin can mostly reach 90% or above; the method is cheap in substrate, easy in substrate obtaining, simple to operate, environmentally friendly, high in yield and the like; the low-cost, high-efficiency, clean and environment-friendly method is easy to achieve industrial production and promisingin application prospect.
Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides
Teng, Shenghan,Tessensohn, Malcolm E.,Webster, Richard D.,Zhou, Jianrong Steve
, p. 7439 - 7444 (2018/07/15)
The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides, ring opening occurs selectively at terminal positions, and stereocenters of epoxides are fully retained. Mechanistic studies provide evidence for in situ conversion of epoxides to β-halohydrins, generation of alkyl radicals, and radical addition to alkenes as key steps. Cyclovoltammetric determination of reduction potentials suggests that during activation of alkyl iodides by palladium(0) complexes, inner-sphere halogen abstraction is more likely than outer-sphere single electron transfer.
Rhodium-Catalyzed Generation of Anhydrous Hydrogen Iodide: An Effective Method for the Preparation of Iodoalkanes
Zeng, Chaoyuan,Shen, Guoli,Yang, Fan,Chen, Jingchao,Zhang, Xuexin,Gu, Cuiping,Zhou, Yongyun,Fan, Baomin
, p. 6859 - 6862 (2018/10/25)
The preparation of anhydrous hydrogen iodide directly from molecular hydrogen and iodine using a rhodium catalyst is reported for the first time. The anhydrous hydrogen iodide generated was proven to be highly active in the transformations of alkenes, phenyl aldehydes, alcohols, and cyclic ethers to the corresponding iodoalkanes. Therefore, the present methodology not only has provided convenient access to anhydrous hydrogen iodide but also offers a practical preparation method for various iodoalkanes in excellent atom economy.
Halohydrin and its derivatives low priced high-efficient synthetic method (by machine translation)
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Paragraph 0160; 0161; 0162; 0163, (2017/08/25)
The invention discloses a halohydrin low priced high-efficient synthetic method, the organic solvent of formula I shown in the olefin compound with a halide, sulfoxide and additive mixing, by the olefin of hydroxy halogenate reaction, can be a high selectivity of the halohydrin the system results in the type II shown, wherein R1 , R2 , R3 , R4 , R5 And R6 Are selected from hydrogen, halogen, alkyl, hydroxyalkyl, alkoxy, ester, acyl, amido, dialkyl amino, aryl, substituted aromatic, heterocyclic aromatic group or substituted heterocyclic aromatic, R1 , R2 , R3 , R4 , R5 And R6 The presence of the respective independent may be identical or different; or R1 And R2 , R1 And R3 , R2 And R4 , R3 And R4 , R5 And R6 Combining to form a cycloalkyl or substituted cycloalkyl, benzo ring alkyl or substituted cycloalkyl, heterocycle or substituted heterocycle; M selected from hydrogen, lithium, sodium, potassium, cesium, beryllium, magnesium, calcium, strontium, barium, zinc, copper, iron, ammonium or tetraalkyl ammonium; X chlorine, bromine or iodine. (by machine translation)
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.
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.
1,3,2,4-diazadiphosphetidine-based phosphazane oligomers as source of P(III) atom economy reagents: Conversion of epoxides to vic -haloalcohols, vic -dihalides, and alkenes in the presence of halogen sources
Iranpoor, Nasser,Firouzabadi, Habib,Etemadidavan, Elham
, p. 1165 - 1173 (2014/10/16)
1,3,2,4-Diazadiphosphetidines (P1-P3), as easily prepared, stable, and heterogeneous P(III) compounds, were used for the efficient conversion of epoxides to vic-halohydrins, vic-dihalides, or alkenes in the presence of different halogen sources in CH3CN. Of these phosphazanes, P3 is most suitable and contains 4 phosphorous atoms with the advantage of having greater atom economy and its phosphorus oxide byproduct can be easily separated from the reaction mixture by simple filtration. The nitrogen atoms in this molecule can also act as acid scavengers in the reaction.
Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols
Kolodiazhna, Olga O.,Kolodiazhna, Anastasy O.,Kolodiazhnyi, Oleg I.
, p. 37 - 42 (2013/02/25)
The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation.
