29264-40-2Relevant academic research and scientific papers
A Mild and Convenient Procedure for Conversion of Alkenes into Alkyl Iodides via Reaction of Iodine Monochloride with Organoboranes
Kabalka, George W.,Gooch, Eugene E.
, p. 3578 - 3580 (1980)
Alkenes are rapidly converted to alkyl iodides under mild conditions via a hydroboration-iodination sequence which utilizes iodine monochloride as the iodination agent.The iodination proceeds with inversion of configuration.A series of functionally substituted iodides was synthesized via the new products.
Photoorganocatalytic Atom Transfer Radical Addition of Bromoacetonitrile to Aliphatic Olefins
Voutyritsa, Errika,Nikitas, Nikolaos F.,Apostolopoulou, Mary K.,Gerogiannopoulou, Anna Dimitra D.,Kokotos, Christoforos G.
, p. 3395 - 3401 (2018)
A green and cheap protocol for the photocatalytic atom transfer radical addition (ATRA) of bromoacetonitrile to aliphatic alkenes is presented. The use of benzoin methyl ehter as the photocatalyst and irradiation using a household lightbulb leads to a hig
Regiodivergent Conversion of Alkenes to Branched or Linear Alkylpyridines
Kim, Minseok,Shin, Sanghoon,Koo, Yejin,Jung, Sungwoo,Hong, Sungwoo
supporting information, p. 708 - 713 (2022/01/20)
Herein we report a practical protocol for the visible-light-induced regiodivergent radical hydropyridylation of unactivated alkenes using pyridinium salts. This approach provides a unified synthetic platform to control the regioselectivity of the synthesis of linear or branched C4-alkylated pyridines. A remarkable selectivity switch from the anti-Markovnikov to the Markovnikov product can be achieved by the addition of tetrabutylammonium bromide. The versatility of this protocol is further demonstrated based on the late-stage functionalization in pharmaceuticals.
Tautomycetin Synthetic Analogues: Selective Inhibitors of Protein Phosphatase I
Woydziak, Zachary R.,Yucel, A. John,Chamberlin, A. Richard
, p. 839 - 850 (2020/12/15)
Ser/Thr protein phosphatases (PPs) regulate a substantial range of cellular processes with protein phosphatases 1 (PP1) and 2 A (PP2A) accounting for over 90 % of the activity within cells. Nevertheless, tools to study PPs are limited as PPs inhibitors, particularly those selective for PP1 inhibition, are relatively scarce. Two examples of PP1-selective inhibitors, which share structural similarities, are tautomycin (TTM) and tautomycetin (TTN). This work describes the development of PP1/PP2A inhibitors that incorporate key structural features of TTM and TTN and are designed to conserve regions known to bind the active site of PP1/PP2A but vary regions that differentially contact the hydrophobic groove of PP1/PP2A. In all 28 TTN analogues were synthetically generated that inhibit PP1/PP2A activity at 50 values were determined for the seven most active analogues, which ranged from 34 to 1500 nM (PP1) and 70 to 6800 nM (PP2A). Four of the seven analogues possessed PP1 selectivity, and one demonstrated eightfold selectivity in the nanomolar range (PP1 IC50=34 nM, PP2A IC50=270 nM). A rationale is given for the observed differences in selectivity.
Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
Cruz, Daniel A.,Sinka, Victoria,De Armas, Pedro,Steingruber, Hugo Sebastian,Fernández, Israel,Martín, Víctor S.,Miranda, Pedro O.,Padrón, Juan I.
supporting information, p. 6105 - 6109 (2021/08/18)
A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui's radical susceptibilities support the obtained results.
3,6-DIAMINO-PYRIDAZIN-3-YL DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USES AS PRO-APOPTOTIC AGENTS
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Page/Page column 49, (2021/02/05)
Compounds of formula (I) wherein Het1, Het2, R1, R2 and R3 are as defined in the description. Medicaments.
Nickel-Catalyzed Hydrosilylation of Terminal Alkenes with Primary Silanes via Electrophilic Silicon-Hydrogen Bond Activation
Wu, Xiaoyu,Ding, Guangni,Lu, Wenkui,Yang, Liqun,Wang, Jingyang,Zhang, Yuxuan,Xie, Xiaomin,Zhang, Zhaoguo
supporting information, p. 1434 - 1439 (2021/02/16)
We report a simple and effective nickel-based catalytic system, NiCl2·6H2O/tBuOK, for the electrophilically activated hydrosilylation of terminal alkenes with primary silanes. This protocol provides excellent performance under mild reaction conditions: ex
Ni-Catalyzed Carboxylation of Aziridines en Route to β-Amino Acids
Davies, Jacob,Janssen-Müller, Daniel,Zimin, Dmitry P.,Day, Craig S.,Yanagi, Tomoyuki,Elfert, Jonas,Martin, Ruben
supporting information, p. 4949 - 4954 (2021/04/07)
A Ni-catalyzed reductive carboxylation of N-substituted aziridines with CO2 at atmospheric pressure is disclosed. The protocol is characterized by its mild conditions, experimental ease, and exquisite chemo- and regioselectivity pattern, thus unlocking a new catalytic blueprint to access β-amino acids, important building blocks with considerable potential as peptidomimetics.
Metal-free Photochemical Atom Transfer Radical Addition (ATRA) of BrCCl3 to Alkenes
Nikitas, Nikolaos F.,Voutyritsa, Errika,Gkizis, Petros L.,Kokotos, Christoforos G.
supporting information, p. 96 - 101 (2021/01/04)
A simple, photochemical, and metal-free protocol for the atom transfer radical addition (ATRA) of bromotrichloromethane onto various alkenes is described. Among a range of organic molecules, phenylglyoxylic acid proved to be the most suitable photoinitiator to promote a sustainable process for the addition of bromotrichloromethane to olefins. This photochemical atom transfer radical protocol can be expanded into a wide substrate scope of aliphatic olefins bearing various functional groups, leading to the corresponding products in good to excellent yields.
Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes
Lu, Zhichao,Hennis, Olivia,Gentry, Joseph,Xu, Bo,Hammond, Gerald B.
supporting information, p. 4383 - 4388 (2020/06/04)
The base-induced reaction of aryl diazonium salts with commercially available CF3SO2Na/CF2HSO2Na allows for the generation of the corresponding diazene radicals along with fluoromethyl radicals. The addition of fluoromethyl radicals to alkenes with subsequent diazene trapping provides the azofluoromethylation products in good to excellent yields. This metal-free method under mild reaction conditions has broad functional group compatibility and is applicable in the late-stage modification of various natural products and bioactive molecules.
