90003-91-1Relevant academic research and scientific papers
Structural elaboration of the surprising ortho-zincation of benzyl methyl ether
Balloch, Liam,Kennedy, Alan R.,Klett, Jan,Mulvey, Robert E.,O'Hara, Charles T.
, p. 2319 - 2321 (2010)
Breaking with convention, the reaction of the sodium zincate, [(TMEDA)Na(μ-TMP)(μ-tBu)Zn(tBu)] with benzyl methyl ether (PhCH2OMe) produces exclusively an ortho-zincated intermediate [(TMEDA)Na(μ-TMP)(μ-C6H
One-Pot Synthesis and Conformational Analysis of Six-Membered Cyclic Iodonium Salts
Caspers, Lucien D.,Spils, Julian,Damrath, Mattis,Lork, Enno,Nachtsheim, Boris J.
, p. 9161 - 9178 (2020/08/14)
Two one-pot procedures for the construction of carbon-bridged diaryliodonium triflates and tetrafluoroborates are described. Strong Br?nsted acids enable the effective Friedel-Crafts alkylation with diversely substituted o-iodobenzyl alcohol derivatives, providing diphenylmethane scaffolds, which are subsequently oxidized and cyclized to the corresponding dibenzo[b,e]iodininium salts. Based on NMR investigations and density functional theory (DFT) calculations, we could verify the so-far-undescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge.
Photoactivated N-Acyliminoiodinanes Applied to Amination: an ortho-Methoxymethyl Group Stabilizes Reactive Precursors
Kobayashi, Yusuke,Masakado, Sota,Takemoto, Yoshiji
supporting information, p. 693 - 697 (2018/01/17)
N-Acyliminoiodinanes were characterized for the first time by X-ray structural analysis. The ortho-methoxymethyl group and the carbonyl oxygen coordinate to the iodine atom of the iminoiodinane. Activation of the N-acyliminoiodinane was achieved by photoirradiation at 370 nm, thereby enabling reaction with various silyl enol ethers to give α-aminoketone derivatives in good to high yield. N-sulfonyliminoiodinanes bearing ortho substituents were used in photoinduced amination.
Catalyst-Free Aromatic Radiofluorination via Oxidized Iodoarene Precursors
Kwon, Young-Do,Son, Jeongmin,Chun, Joong-Hyun
supporting information, p. 7902 - 7906 (2019/01/04)
Oxidized iodoarenes (OIAs), prepared via mCPBA-mediated oxidation, have been demonstrated as versatile precursors for the synthesis of [18F]fluoroarenes in the absence of catalysts. OIAs have been identified as intermediates in single-pot syntheses of iodonium salts and ylides but have never been recognized as radiofluorination precursors. Here, the isolated OIAs were used without any catalysts to produce functionalized [18F]fluoroarenes, regardless of the electronic nature of the arenes. This method was also applied to the production of radiolabeling synthons for use as aromatic 18F-labeled building blocks.
ALKYNYL PHOSPHINE GOLD COMPLEXES FOR TREATING BACTERIAL INFECTIONS
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Page/Page column 109, (2017/08/01)
A compound of formula (I) for use in the prevention or treatment of a bacterial infection.
Diisobutylaluminum hydride-promoted cyclization of benzyl and phenylsilyl ethers bearing a 2-(trimethylsilyl)ethynyl group: syntheses of indenes and benzosiloles
Kinoshita, Hidenori,Fukumoto, Hiroki,Tohjima, Takayuki,Miura, Katsukiyo
supporting information, p. 3571 - 3574 (2016/07/18)
The reaction of o-[2-(trimethylsilyl)ethynyl]benzyl methyl ethers with diisobutylaluminum hydride (DIBAL-H) gave 2-(trimethylsilyl)indenes in good yields. This cyclization proceeds by regio- and stereoselective hydroalumination of the alkyne moiety followed by intramolecular nucleophilic substitution. o-[2-(Trimethylsilyl)ethynyl]phenylsilyl methyl ethers also underwent the DIBAL-H promoted-cyclization to be converted into 2-(trimethylsilyl)benzosiloles in good yields. This approach provides straightforward and efficient way to construct benzosiloles from readily available organosilanes.
Gold(I)-Catalyzed Intramolecular Carbon-Oxygen Bond Cleavage Reaction via Gold Carbenes Derived from Vinylidenecyclopropanes
Li, De-Yao,Wei, Yin,Shi, Min
supporting information, p. 3002 - 3009 (2016/10/09)
Under gold(I) catalysis, the in situ generated gold carbene from vinylidenecyclopropanes bearing a methoxymethyl group can undergo an intramolecular nucleophilic attack to give the carbon-oxygen bond cleavage product in good yield within 15 min. and different phosphine ligands could control both Z- and E-configurations, respectively. The reaction mechanism has been clarified on the basis of deuterium- and18O-labeling experiments. This method provides a new and efficient approach to stereoselectively synthesize alkylidenecyclobutanones under mild conditions. (Figure presented.).
A concise synthesis of chiral indanes as α1A adrenoceptor partial agonists
Roberts, Lee R.,Corbett, Matthew S.,Fussell, Steven J.,Hitzel, Laure,Jessiman, Alan S.,Mason, Helen J.,Osborne, Rachel,Ralph, Michael J.,Stennett, Adam S.D.,Wheeler, Simon,Storer, R. Ian
supporting information, p. 6546 - 6550 (2015/11/09)
The synthesis of a series of chiral indanes with reported α1A partial agonist activity is outlined, applying a rhodium catalysed cyclisation for template construction. This method was extended to the asymmetric synthesis of lead compound PF-037
Preparation of 1,1′-oxy-bis(3,3-bis(trifluoromethyl)-3(1H)-1,2- benziodoxole) and 2-(N-(p-toluenesulfonyl)imino)iodobenzylmethyl ether
Blake, Alexander J.,Novak, Andrew,Davies, Madeline,Robinson, Richard I.,Woodward, Simon
experimental part, p. 1065 - 1075 (2009/09/08)
Conditions for improved preparation of the crystalline iodine(III) reagents [1,2-C6H4(C(CF3)2OI)]2O and 1,2-C6H4(CH2OMe)(I=NTs) are presented together with their x-ray structures. The former is prepared by hydrolysis of 1,2-C6H4(C(CF3)2OICl (x-ray) and allows the preparation of cyclic sulfates from alkenes; the latter fashions sulfamidate under related conditions. Copyright Taylor & Francis Group, LLC.
Mercury in Organic Chemistry. 26. Synthesis of Heterocycles via Intramolecular Solvomercuration of Aryl Acetylenes
Larock, Richard C.,Harrison, L. Wayne
, p. 4218 - 4227 (2007/10/02)
A number of ortho substituted aryl acetylenes, o-CH3XC6H4YCCR (X=O, S, CO2; Y=-, CO), have been observed to undergo facile intramolecular solvomercuration with mercuric acetate in acetic acid to afford the corresponding benzofuran, benzothiophene, isocoumarin, and chromone organomercuric chlorides, after aqueous sodium chloride workup.The aryl acetylenes m-XC6H4YCH2CCR (X=H, Y=O, R=CH3; X=CH3O, Y=CH2, R=n-C3H7) undergo similar cyclizations to yield mercurated 2H-1-benzopyrans and 1,2-dihydronaphthalenes.The mercuration and subsequent carbonylation of o-R1OC6H4CCR2 1=Si(t-Bu)Me2, R2=CH3; R1=CH3, R2=o-C6H4OCH3> has provided a new approach to the coumarin and coumestan ring systems.
