57308-70-0Relevant articles and documents
Metal-Free, N-Iodosuccinimide-Induced Regioselective Iodophosphoryloxylation of Alkenes with P(O)?OH Bonds
Xiong, Biquan,Xu, Shipan,Zhu, Yu,Yao, Lei,Zhou, Congshan,Liu, Yu,Tang, Ke-Wen,Wong, Wai-Yeung
supporting information, p. 9556 - 9560 (2020/07/13)
A simple and efficient method for the regioselective iodophosphoryloxylation of alkenes with P(O)?OH bonds has been established by using NIS (N-iodosuccinimide) as the iodination reagent under transition-metal-free conditions. The present protocol is compatible with different functional groups, and suitable for various alkenes and P(O)?OH compounds. A variety of functionalized β-iodo-1-ethyl phosphinic/phosphoric acid esters are obtained in good to excellent yields, which could be further transformed to diversified building blocks for the synthesis of bioactive compounds, pharmaceuticals and functional materials.
Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
Citarella, Andrea,Holzer, Wolfgang,Ielo, Laura,Langer, Thierry,Miele, Margherita,Pace, Vittorio,Urban, Ernst,Zehl, Martin
supporting information, p. 7629 - 7634 (2020/10/12)
The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
Reaction of N,N′-Methylenebis(trifluoromethanesulfonamide) with Styrene under Oxidative Conditions
Moskalik, M. Yu.,Astakhova,Ganin,Shainyan
, p. 734 - 736 (2019/07/17)
The reaction of N,N′-methylenebis(trifluoromethanesulfonamide) with styrene in the oxidative system t-BuOCl/NaI affords triflamide, 2-iodo-1-phenylethanol, N,N′-bis(trifluoromethanesulfonyl)urea, and the product of styrene bistriflamidation. The mechanism
Facile iodination of the vinyl groups in protoporphyrin IX dimethyl ester and subsequent transformation of the iodinated moieties
Miyata, Kota,Yasuda, Satoru,Masuya, Takuto,Ito, Satoshi,Kinoshita, Yusuke,Tamiaki, Hitoshi,Oba, Toru
, p. 3707 - 3711 (2018/05/28)
Iodination of protoporphyrin IX dimethyl ester using phenyliodine bis(trifluoroacetate) (PIFA) and I2 was studied. Iodine added to both the C3- and C8-vinyl groups equally to afford the iodohydrin or iodoether in the presence of water or alcohol, respectively. Any meso-hydrogen atom was not substituted by an iodine atom under these conditions, although both the vinyl group and one of the meso positions of methyl pyropheophorbide-a bearing a chlorin π-system, a chlorophyll-a derivative, was modified with PIFA and I2. The reaction intermediates derived from the porphyrin were more reactive than those from the chlorin and liable to form intermolecular linkages. The obtained 2-iodo-1-hydroxyethyl group was transformed into a formyl group by a mild treatment. The corresponding iodoether moiety was readily converted into the acetyl group under basic conditions. These transformations were also applicable to smaller olefins such as styrene.
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.
Halohydrin and its derivatives low priced high-efficient synthetic method (by machine translation)
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Paragraph 0144; 0145; 0146; 0147, (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.
Benzyl(triphenyl)phosphonium Dichloroiodate: A New Reagent for Coiodination of Alkenes
Alikarami, Mohammad,Farhadi, Mansoureh
, p. 1302 - 1306 (2015/09/22)
A mild, efficient, and regio- and stereoselective method for iodoalkoxylation and iodohydroxylation of olefins has been developed using benzyl(triphenyl)phosphonium dichloroiodate as iodine source. This procedure led to the corresponding iodoalkoxylated and iodohydroxylated products in moderate to excellent yields.
PROCESS FOR THE PREPARATION OF N-IODOAMIDES
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Paragraph 00263-00264, (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.
