35779-04-5Relevant articles and documents
AROMATIC IODINATION BY POSITIVE IODINE ACTIVE SPECIES GENERATED BY ANODIC OXIDATION IN TRIMETHYL ORTHOFORMATE
Shono, Tatsuya,Matsumura, Yoshihiro,Katoh, Susumu,Ikeda, Kaoru,Kamada, Tohru
, p. 1649 - 1650 (1989)
Anodic oxidation of iodine in trimethyl orthoformate afforded a solution of positive iodine active species which brought about more selective aromatic iodination than the hitherto known other methods.
A palladium-catalyzed C-H functionalization route to ketones: Via the oxidative coupling of arenes with carbon monoxide
Arndtsen, Bruce A.,Kinney, R. Garrison,Levesque, Taleah M.
, p. 3104 - 3109 (2020/03/27)
We describe the development of a new palladium-catalyzed method to generate ketones via the oxidative coupling of two arenes and CO. This transformation is catalyzed by simple palladium salts, and is postulated to proceed via the conversion of arenes into high energy aroyl triflate electrophiles. Exploiting the latter can also allow the synthesis of unsymmetrical ketones from two different arenes.
Generation of Organozinc Reagents from Arylsulfonium Salts Using a Nickel Catalyst and Zinc Dust
Yamada, Kodai,Yanagi, Tomoyuki,Yorimitsu, Hideki
, p. 9712 - 9718 (2021/01/09)
Readily available aryldimethylsulfonium triflates react with zinc powder under nickel catalysis via the selective cleavage of the sp2-hybridized carbon-sulfur bond to produce salt-free arylzinc triflates under mild conditions. This zincation displays superb chemoselectivity and thus represents a protocol that is complementary or orthogonal to existing methods. The generated arylzinc reagents show both high reactivity and chemoselectivity in palladium-catalyzed and copper-mediated cross-coupling reactions.
Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates
Klein, Philippe,Lechner, Vivien Denise,Schimmel, Tanja,Hintermann, Lukas
, p. 176 - 180 (2019/12/11)
The generation of arylzinc reagents (ArZnX) by direct insertion of zinc into the C?X bond of ArX electrophiles has typically been restricted to iodides and bromides. The insertions of zinc dust into the C?O bonds of various aryl sulfonates (tosylates, mesylates, triflates, sulfamates), or into the C?X bonds of other moderate electrophiles (X=Cl, SMe) are catalyzed by a simple NiCl2–1,4-diazadiene catalyst system, in which 1,4-diazadiene (DAD) stands for diacetyl diimines, phenanthroline, bipyridine and related ligands. Catalytic zincation in DMF or NMP solution at room temperature now provides arylzinc sulfonates, which undergo typical catalytic cross-coupling or electrophilic substitution reactions.
Synthesis of pure blue emissive poly(2,7-carbazole)s anchored by electron donor pendant
Inada, Takashi,Shinnai, Toshinobu,Kijima, Masashi
, p. 2526 - 2534 (2019/11/03)
Three novel poly(2,7-carbazole)s having hole injection and transporting pendent moieties of carbazole and triphenylamine at the N-position were synthesized for achieving pure blue electroluminescence. The N-pendants in the polymers correspond to N-phenylcarbazol-2-yl (P1), N,N-diphenylamino-N-phenylcarabazol-2-yl (P2), and 4-phenyl having a hydrocarbon chain with a triphenylamine terminal (P3), respectively. Electronic, optical, and electroluminescence properties of these polymers were compared with those of a poly(2,7-carbazole) directly connected with triphenylamine at the N-position (P0) having an aggregation-induced emissive property. The photoluminescence (PL) spectra suggested that they could emit in the region of blue light in the film state. Especially, P2 that has the fixed and large diphenylaminocarbazolyl pendant showed a deep-blue fluorescence with CIE(x, y) = (0.15, 0.07). The P0, P2, and P3 based light emitting diode devices showed maximum electroluminescence wavelengths in the range of 430–450 nm. The P2 device showed pure blue emission (CIE[x, y] = [0.18, 0.16]), high luminance (1130 cd/m2) and current density (628 mA/cm2) at 8 V, whereas low-energy emissions around 500–600 nm were emerged at higher than 9 V. The P0 and P3 devices also showed a blue electroluminescence in the range of 8–11 V, but their luminance and efficiency were low.
Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds
Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi
, (2019/06/13)
Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.
Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds
Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi
, p. 7411 - 7417 (2019/06/18)
Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.
One of iodinated aromatic ring by iodine chloride in hydrochloric acid (by machine translation)
-
Paragraph 0072-0076, (2019/09/10)
[Problem] to one iodine chloride is used, and, stably iodinated aromatic compound can be iodinated aromatic compound production. [Solution] water containing one iodine chloride hydrogen chloride, iodine chloride content of 30% by mass of the first mass % -70, 3 mass % -20 mass % aqueous solution of hydrogen chloride content in the preparing step, a process for preparing an aromatic compound as the reaction substrate, the reaction substrate as an aqueous solution of the mixture of aromatic compounds, as the reaction substrate of one iodine chloride by reacting an aromatic compound, iodinated aromatic compound obtained in the step, the iodinated aromatic compound. [Drawing] no (by machine translation)
Visible-Light-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions
Patra, Tuhin,Mukherjee, Satobhisha,Ma, Jiajia,Strieth-Kalthoff, Felix,Glorius, Frank
, p. 10514 - 10520 (2019/07/12)
Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond-forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single-electron-transfer mechanism and “switch on” an energy-transfer-mediated homolysis of unsymmetrical σ-bonds for a concerted fragmentation/decarboxylation process.
Synthesis of phenols and aryl silyl ethers via arylation of complementary hydroxide surrogates
Reitti, Marcus,Gurubrahamam, Ramani,Walther, Melanie,Lindstedt, Erik,Olofsson, Berit
supporting information, p. 1785 - 1788 (2018/04/14)
Two transition-metal-free methods to access substituted phenols via the arylation of silanols or hydrogen peroxide with diaryliodonium salts are presented. The complementary reactivity of the two nucleophiles allows synthesis of a broad range of phenols without competing aryne formation, as illustrated by the synthesis of the anesthetic Propofol. Furthermore, silyl-protected phenols can easily be obtained, which are suitable for further transformations.