20651-71-2Relevant academic research and scientific papers
A new synthetic method for para alkylation of benzoic acids using metallic strontium and alkyl iodide
Miyoshi, Norikazu,Matsuo, Tsuyoshi,Mori, Mariko,Matsui, Aki,Kikuchi, Makoto,Wada, Makoto,Hayashi, Masahiko
, p. 996 - 997 (2009)
Aromatic carboxylic acids reacted with metallic strontium and alkyl iodides to give para alkylated products preferentially in moderate to good yields. Copyright
Cobalt-Catalyzed Deprotection of Allyl Carboxylic Esters Induced by Hydrogen Atom Transfer
Li, Nan,Gui, Yizhen,Chu, Mengqi,You, Mengdi,Qiu, Xiaohan,Liu, Hejia,Wang, Shiang,Deng, Meng,Ji, Baoming
supporting information, p. 8460 - 8464 (2021/11/13)
A brief, efficient method has been developed for the removal of the allyl protecting group from allyl carboxylic esters using a Co(II)/TBHP/(Me2SiH)2O catalytic system. This facile strategy displays excellent chemoselectivity, functional group tolerance, and high yields. This transformation probably occurs through the hydrogen atom transfer process, and a Co(III)-six-membered cyclic intermediate is recommended.
Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands
Dilauro, Giuseppe,Azzollini, Claudia S.,Vitale, Paola,Salomone, Antonio,Perna, Filippo M.,Capriati, Vito
supporting information, p. 10632 - 10636 (2021/04/09)
Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.
Cobalt-catalyzed carboxylation of aryl and vinyl chlorides with CO2
Wang, Yanwei,Jiang, Xiaomei,Wang, Baiquan
supporting information, p. 14416 - 14419 (2020/12/01)
The transition-metal-catalyzed carboxylation of aryl and vinyl chlorides with CO2 is rarely studied, and has been achieved only with a Ni catalyst or combination of palladium and photoredox. In this work, the cobalt-catalyzed carboxylation of aryl and vinyl chlorides and bromides with CO2 has been developed. These transformations proceed under mild conditions and exhibit a broad substrate scope, affording the corresponding carboxylic acids in good to high yields.
Single-Electron-Transfer-Induced Coupling of Alkylzinc Reagents with Aryl Iodides
Okura, Keisho,Shirakawa, Eiji
supporting information, p. 3043 - 3046 (2016/07/14)
Alkylzinc reagents prepared from an alkyllithium and zinc iodide were found to undergo coupling with aryl and alkenyl iodides in the presence of LiI in a mixed solvent consisting of THF and diglyme (1:1). Alkyllithiums, prepared by halogen–lithium exchange between an alkyl iodide and tert-butyllithium, are also converted to alkylarenes through alkylzinc reagents.
A Strained Disilane-Promoted Carboxylation of Organic Halides with CO2 under Transition-Metal-Free Conditions
Mita, Tsuyoshi,Suga, Kenta,Sato, Kaori,Sato, Yoshihiro
supporting information, p. 5276 - 5279 (2015/11/18)
By using a strained four-membered ring disilane (3,4-benzo-1,1,2,2-tetraethyldisilacyclobutene) and CsF, a wide range of aryl, alkenyl, alkynyl, benzyl, allyl, and alkyl halides was successfully carboxylated under an ambient CO2 atmosphere (CO2 balloon) at room temperature within 2 h. In this carboxylation, a highly reactive silyl anion, which is generated from the disilane and CsF, is a key to facilitating the formation of a carbanion equivalent. The resulting anionic species can be trapped with CO2 to produce carboxylic acids with high efficiency.
An outstanding catalyst for the oxygen-mediated oxidation of arylcarbinols, arylmethylene and arylacetylene compounds
Urgoitia,Sanmartin,Herrero,Domínguez
supporting information, p. 4799 - 4802 (2015/03/18)
A convenient and sustainable protocol for the aerobic oxidation of benzyl alcohols to carbonyl compounds, based on the use of 1,2,4-triazole-type ligands and nickel(ii) bromide, is described. This combination leads to the formation of an exceedingly active, enzyme-like system that allows for other oxidative processes, such as benzylic C-H oxidation and oxygen-mediated cleavage of C-C triple bond, a pioneering procedure for transformation of alkynes into carboxylic acids.
Palladium on carbon-catalyzed aqueous transformation of primary alcohols to carboxylic acids based on dehydrogenation under mildly reduced pressure
Sawama, Yoshinari,Morita, Kosuke,Asai, Shota,Kozawa, Masami,Tadokoro, Shinsuke,Nakajima, Junichi,Monguchi, Yasunari,Sajiki, Hironao
supporting information, p. 1205 - 1210 (2015/04/22)
The catalytic dehydrogenation of alcohols to carbonyl products is a green sustainable oxidation with no production of waste except for hydrogen, which can be an energy source. Additionally, a reusable heterogeneous catalyst is valuable from the viewpoint of process chemistry and water is a green solvent. We have accomplished the palladium on carbon (Pd/C)-catalyzed dehydrogenation of primary alcohols to carboxylic acids in water under a mildly reduced pressure (800 hPa). The reduced pressure can be easily controlled by the vacuum controller of the rotary evaporator to remove the excess of generated hydrogen, which causes the reduction (reverse reaction) of aldehydes to alcohols (starting materials) and other undesirable side reactions. The present method is applicable to the reaction of various aliphatic and benzylic alcohols to the corresponding carboxylic acids, and the Pd/C could be reused at least 5 times.
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.
Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4
MacNair, Alistair J.,Tran, Ming-Ming,Nelson, Jennifer E.,Sloan, G. Usherwood,Ironmonger, Alan,Thomas, Stephen P.
supporting information, p. 5082 - 5088 (2014/07/08)
An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(iii) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.
