13132-15-5Relevant articles and documents
On the origins of stereoselectivity in the aminocatalytic remote alkylation of 5-alkylfurfurals
Dyguda, Mateusz,Przydacz, Artur,Krzemińska, Agnieszka,Albrecht, ?ukasz
, p. 6025 - 6031 (2019)
In the manuscript, computational studies on the remote alkylation of 5-alkylfurfurals proceeding via formation of the corresponding trienamine intermediate are presented. By the means of density functional theory (DFT) calculations and the symmetry-adapte
Method for reducing carbonyl reduction to methylene under illumination
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Paragraph 0033-0038; 0145-0149, (2021/09/29)
The invention belongs to the technical field of organic chemical synthesis. The method comprises the following steps: (1) mixing the carbonyl compound and the amine compound in a solvent, reacting 3 - 6 under the illumination of 380 - 456 nm, the reaction system is low in toxicity, high in atom utilization rate 12 - 24h. and production efficiency, safe and controllable in reaction process and capable of simplifying the operation in the preparation and production process. At the same time, the residue toxicity of the reaction is minimized, the pollution caused by the production process to the environment is reduced, and the steps and operations of removing residues after the reaction are simplified. In addition, the reactant feedstock is readily available. The reactant does not need additional modification before the reaction, can be directly used for preparing production, simplifies the operation steps, and shortens the reaction route. The production cost is obviously reduced.
Photo-Ni-Dual-Catalytic C(sp2)-C(sp3) Cross-Coupling Reactions with Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Semiconductor Photocatalyst
Antonietti, Markus,Ghosh, Indrajit,K?nig, Burkhard,Khamrai, Jagadish,Savateev, Aleksandr
, p. 3526 - 3532 (2020/04/09)
The synergistic combination of a heterogeneous organic semiconductor mesoporous graphitic carbon nitride (mpg-CN) and a homogeneous nickel catalyst with visible-light irradiation at room temperature affords the C(sp2)-C(sp3) cross-co
Electrochemical Hydrogenation with Gaseous Ammonia
Li, Jin,He, Lingfeng,Liu, Xu,Cheng, Xu,Li, Guigen
supporting information, p. 1759 - 1763 (2019/01/16)
As a carbon-free and sustainable fuel, ammonia serves as high-energy-density hydrogen-storage material. It is important to develop new reactions able to utilize ammonia as a hydrogen source directly. Herein, we report an electrochemical hydrogenation of alkenes, alkynes, and ketones using ammonia as the hydrogen source and carbon electrodes. A variety of heterocycles and functional groups, including for example sulfide, benzyl, benzyl carbamate, and allyl carbamate were well tolerated. Fast stepwise electron transfer and proton transfer processes were proposed to account for the transformation.
Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols
Xia, Anjie,Qi, Xueyu,Mao, Xin,Wu, Xiaoai,Yang, Xin,Zhang, Rong,Xiang, Zhiyu,Lian, Zhong,Chen, Yingchun,Yang, Shengyong
supporting information, (2019/05/07)
A transition-metal-free aerobic oxidative selective C-C bond-cleavage reaction in primary and secondary heteroaryl alcohols is reported. This reaction was highly efficient and tolerated various heteroaryl alcohols, generating a carboxylic acid derivative and a neutral heteroaromatic compound. Experimental studies combined with density functional theory calculations revealed the mechanism underlying the selective C-C bond cleavage. This strategy also provides an alternative simple approach to carboxylation reaction.
Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On-Water Conditions
La Manna, Pellegrino,Soriente, Annunziata,De Rosa, Margherita,Buonerba, Antonio,Talotta, Carmen,Gaeta, Carmine,Neri, Placido
, p. 1673 - 1683 (2019/03/26)
Metal-free Friedel–Crafts benzylation (FCB) of scarcely reactive arenes and heteroarenes was performed under on-water conditions by an environmentally sustainable procedure. The catalytic strategy exploits the hydrophobicity of the resorcinarene macrocycle 1 a. The proposed mechanism is based on the activation of benzyl chloride by H-bonding interactions with catalyst 1 a. In fact, under on-water conditions the hydrophobic amplification of the strength of the H-bonding interactions between the OH groups of the resorcinarene catalyst and the chlorine atom of benzyl chloride leads to polarization of the C?Cl bond, which consequently promotes electrophilic attack of the π nucleophile. Thus, many arenes and heteroarenes were efficiently benzylated under mild on-water conditions by using resorcinarene 1 a as catalyst. The FCB of benzene is industrially relevant for the synthesis of diphenylmethane, and hence the on-water procedure was extended to the gram-scale synthesis of diphenylmethane, starting from benzene and benzyl chloride in the presence of resorcinarene catalyst 1 a.
Nickel-Catalyzed Cross-Electrophile Coupling between Benzyl Alcohols and Aryl Halides Assisted by Titanium Co-reductant
Suga, Takuya,Ukaji, Yutaka
, p. 7846 - 7850 (2019/01/14)
A nickel-catalyzed cross-electrophile coupling reaction between benzyl alcohols and aryl halides has been developed using a homolytic C-O bond cleavage protocol that has recently been established. The treatment of a benzyl alcohol and aryl halide with a nickel catalyst and low-valent titanium reagent generated from TiCl4(lutidine) (lutidine = 2,6-lutidine) and manganese powder afforded the cross-coupled product in high yield. A mechanistic study indicated the intermediacy of the benzyl radicals that originate from the benzyl alcohols.
Substrate switchable Suzuki-Miyaura coupling for benzyl ester: Vs. benzyl halide
Ohsumi, Masato,Ito, Akitaka,Nishiwaki, Nagatoshi
, p. 35056 - 35061 (2018/10/24)
Two reaction conditions were developed to accomplish the substrate switchable Suzuki-Miyaura coupling of benzyl derivatives and arylboronic acid derivatives. Under conditions for esters, benzyl esters such as carbonates and acetates reacted with arylboronic acids to afford the corresponding diarylmethanes. However, the benzyl halides did not react under the same conditions. On the other hand, benzyl halides such as bromides and chlorides furnished diarylmethanes under conditions for halides, under which benzyl ester substrates did not react, in which water was found to play an important role. This switching system was tested using the intermolecular/intramolecular competitive reactions, during which the desired products could be synthesized by selecting the appropriate reaction conditions.
Mild Friedel–Crafts Reactions inside a Hexameric Resorcinarene Capsule: C?Cl Bond Activation through Hydrogen Bonding to Bridging Water Molecules
La Manna, Pellegrino,Talotta, Carmen,Floresta, Giuseppe,De Rosa, Margherita,Soriente, Annunziata,Rescifina, Antonio,Gaeta, Carmine,Neri, Placido
, p. 5423 - 5428 (2018/04/09)
A novel catalytic feature of a hexameric resorcinarene capsule is highlighted. The self-assembled cage was exploited to promote the Friedel–Crafts benzylation of several arenes and heteroarenes with benzyl chloride under mild conditions. Calculations showed that there are catalytically relevant hydrogen-bonding interactions between the bridging water molecules of the capsule and benzyl chloride, which is fundamental for the activation of the C?Cl bond. The capsule controls the reaction outcome. Inside the inner cavity of the capsule, N-methylpyrrole is preferentially benzylated in the unusual β-position while mesitylene reacts faster than 1,3-dimethoxybenzene despite the greater π-nucleophilicity of the latter compound.
Nickel-catalyzed cross-coupling of aldehydes with aryl halides: Via hydrazone intermediates
Tang, Jianting,Lv, Leiyang,Dai, Xi-Jie,Li, Chen-Chen,Li, Lu,Li, Chao-Jun
supporting information, p. 1750 - 1753 (2018/02/21)
Traditional cross-couplings require stoichiometric organometallic reagents. A novel nickel-catalyzed cross-coupling reaction between aldehydes and aryl halides via hydrazone intermediates has been developed, merging the Wolff-Kishner reduction and the classical cross-coupling reactions. Aromatic aldehydes, aryl iodides and aryl bromides are especially effective in this new cross-coupling chemistry.
