5680-10-4Relevant articles and documents
Highly-functionalized arene synthesis based on palladium on carbon-catalyzed aqueous dehydrogenation of cyclohexadienes and cyclohexenes
Yasukawa, Naoki,Yokoyama, Hiroki,Masuda, Masahiro,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 1213 - 1217 (2018/03/28)
Transition metal-catalyzed dehydrogenation is a clean oxidation method requiring no additional oxidants. We have accomplished a heterogeneous Pd/C-catalyzed aqueous dehydrogenation of 1,4-cyclohexadienes and cyclohexenes to give the corresponding highly-functionalized arenes. Furthermore, various arenes could be efficiently constructed in a one-pot manner via a Diels-Alder reaction and the following dehydrogenation.
Ligand-accelerated non-directed C-H functionalization of arenes
Wang, Peng,Verma, Pritha,Xia, Guoqin,Shi, Jun,Qiao, Jennifer X.,Tao, Shiwei,Cheng, Peter T. W.,Poss, Michael A.,Farmer, Marcus E.,Yeung, Kap-Sun,Yu, Jin-Quan
, p. 489 - 493 (2017/11/28)
The directed activation of carbon-hydrogen bonds (C-H) is important in the development of synthetically useful reactions, owing to the proximity-induced reactivity and selectivity that is enabled by coordinating functional groups. Palladium-catalysed non-directed C-H activation could potentially enable further useful reactions, because it can reach more distant sites and be applied to substrates that do not contain appropriate directing groups; however, its development has faced substantial challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C-H functionalization with arene as the limiting reagent. This protocol is compatible with a broad range of aromatic substrates and we demonstrate direct functionalization of advanced synthetic intermediates, drug molecules and natural products that cannot be used in excessive quantities. We also developed C-H olefination and carboxylation protocols, demonstrating the applicability of our methodology to other transformations. The site selectivity in these transformations is governed by a combination of steric and electronic effects, with the pyridone ligand enhancing the influence of sterics on the selectivity, thus providing complementary selectivity to directed C-H functionalization.
Inclusion complex containing epoxy resin composition for semiconductor encapsulation
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, (2014/03/21)
The invention is an epoxy resin composition for sealing a semiconductor, including (A) an epoxy resin and (B) a clathrate complex. The clathrate complex is one of (b1) an aromatic carboxylic acid compound, and (b2) at least one imidazole compound represented by formula (II): wherein R2 represents a hydrogen atom, C1-C10 alkyl group, phenyl group, benzyl group or cyanoethyl group, and R3 to R5 represent a hydrogen atom, nitro group, halogen atom, C1-C20 alkyl group, phenyl group, benzyl group, hydroxymethyl group or C1-C20 acyl group. The composition has improved storage stability, retains flowability when sealing, and achieves an effective curing rate applicable for sealing delicate semiconductors.