5381-93-1Relevant academic research and scientific papers
Combination of a Metal-N-Heterocyclic-Carbene Catalyst and a Chiral Aminocatalyst within a Covalent Organic Framework: A Powerful Cooperative Approach for Relay Asymmetric Catalysis
Li, Yue,Wang, Jin-Mei,Kan, Jing-Lan,Li, Fei,Dong, Ying,Dong, Yu-Bin
, p. 2455 - 2462 (2022/01/31)
Incorporation of metal catalysis and organocatalysis has emerged as a promising way for developing new and valuable organic reactions. This catalytic strategy would potentially enable unprecedented transformations not possible by the existing metal cataly
Chiral Bipyridine Ligand with Flexible Molecular Recognition Site: Development and Application to Copper-Catalyzed Asymmetric Borylation of α,β-Unsaturated Ketones
Tsutsumi, Ryosuke,Taguchi, Rika,Yamanaka, Masahiro
, (2021/10/20)
A novel chiral bipyridine ligand bearing a flexible side chain with a molecular recognition site enables precise stereocontrol through the cooperative action of metal center and hydrogen bonds. This new chiral ligand was applied to the copper-catalyzed as
Defect-Engineered Chiral Metal-Organic Frameworks for Efficient Asymmetric Aldol Reaction
Chen, Zijuan,Yan, Xiaodan,Li, Meiyan,Wang, Shuhua,Chen, Chao
supporting information, p. 4362 - 4365 (2021/05/04)
By employment of a mixed truncated chiral ligand synthetic strategy, a defect-engineered chiral metal-organic framework with hierarchical micro/mesoporous structure was prepared, and it exhibited efficient heterogeneous catalytic activity and enantioselectivity for asymmetric aldol reaction.
Near-infrared laser–assisted CuS@mSiO2@L-proline catalyzed asymmetric aldol reaction
Hu, Enyan,Li, Guohua,Xu, Longjun,Zhang, Xiaorui
, (2021/06/22)
Mesoporous silica-coated copper sulfide nanosheet-loaded L-proline catalysts were prepared to catalyze the hydroxyl aldol condensation reaction using 808-nm laser assistance. The catalysts were characterized by X-ray powder diffraction, scanning electron
Chiral imidazolium prolinate salts as efficient synzymatic organocatalysts for the asymmetric aldol reaction
Altava, Belén,Burguete, Maria Isabel,García-Verdugo, Eduardo,Luis, Santiago V.,Porcar, Raúl
supporting information, (2021/07/26)
Chiral imidazolium L-prolinate salts, providing a complex network of supramolecular interaction in a chiral environment, have been studied as synzymatic catalytic systems. They are demonstrated to be green and efficient chiral organocatalysts for direct asymmetric aldol reactions at room temperature. The corresponding aldol products were obtained with moderate to good enantioselectivities. The influence of the presence of chirality in both the imidazolium cation and the prolinate anion on the transfer of chirality from the organocatalyst to the aldol product has been studied. Moreover, interesting match/mismatch situations have been observed regarding configuration of chirality of the two components through the analysis of results for organocatalysts derived from both enantiomers of prolinate (R/S) and the trans/cis isomers for the chiral fragment of the cation. This is associated with differences in the corresponding reaction rates but also to the different tendencies for the formation of aggregates, as evidenced by nonlinear effects studies (NLE). Excellent activities, selectivities, and enantioselectivities could be achieved by an appropriate selection of the structural elements at the cation and anion.
Natural eutectogels: Sustainable catalytic systems for C-C bond formation reactions
D'Anna, Francesca,Meli, Alessandro,Ramón, Diego J.,Rizzo, Carla,Saavedra, Beatriz
supporting information, p. 6555 - 6565 (2021/09/10)
Natural eutectogels were prepared by combining the properties of amino acids with the ones of deep eutectic solvents. The soft materials obtained were fully characterised by determining the gel-sol transition temperatures and analysing the mechanical and
Copper(I) Complexes of P-Stereogenic Josiphos and Related Ligands
Arthurs, Ross A.,Dean, Alice C.,Hughes, David L.,Richards, Christopher J.
supporting information, p. 2719 - 2725 (2021/06/26)
Starting from (R)-Ugi's amine, diastereoselective lithiation followed by Ar'PCl2 and then Ar’’MgBr led to the generation, as single diastereoisomers, of (R,Sp,Sphos) [Ar’=Ph, Ar’’=o-Tol] and (R,Sp,Rphos/su
Highly enantioselective immobilized prolinamide-catalyzed aldol reactions in continuous-flow systems: effect of water on the catalyst lifetime and application in the synthesis of a chiral fenpentadiol analogue
Yue, Caizhen,Yamashita, Yasuhiro,Kobayashi, Shū
supporting information, p. 1989 - 1994 (2021/03/26)
Catalytic enantioselective aldol reactions of trifluoroacetophenones with ketones under continuous-flow conditions have been developed for the first time by using polystyrene-supported prolinamides. The robustness of the flow system was demonstrated by the continuous synthesis of a variety of trifluoromethyl carbinols in high yields with high enantioselectivities. The unusually long lifetimes (>195 h) of this flow process were achieved by facilitating H2O-promoted hydrolysis of iminium intermediates on the polymer. Mechanistic study revealed a racemization phenomenon and an inherent reversible property of the aldol reactions in a conventional batch system, both of which were suppressed under continuous-flow conditions. The synthetic utility of this flow process was further demonstrated by the formal continuous-flow synthesis of a chiral fenpentadiol analogue.
Cellulosic CuI Nanoparticles as a Heterogeneous, Recyclable Catalyst for the Borylation of α,β-Unsaturated Acceptors in Aqueous Media
Zhou, Lijie,Han, Biao,Zhang, Yaoyao,Li, Bojie,Wang, Liansheng,Wang, Jianying,Wang, Xianbao,Zhu, Lei
, p. 3220 - 3229 (2021/03/06)
Abstract: We have demonstrated that cellulosic CuI nanoparticles could perform as an efficient heterogeneous catalyst for the synthesis of useful organoboron compounds. Desired β-borylation products were all obtained in good to excellent yields under mild
Biomass waste-derived recyclable heterogeneous catalyst for aqueous aldol reaction and depolymerization of PET waste
Khiangte, Vanlalngaihawma,Laldinpuii, Z. T.,Lalhmangaihzuala, Samson,Lalmuanpuia, Chhakchhuak,Pachuau, Zodinpuia,Vanlaldinpuia, Khiangte
, p. 19542 - 19552 (2021/11/09)
In this work, we discuss the valorization of biomass waste-derived orange peel ash (OPA) by exploring its applicability as a heterogeneous catalyst in aqueous aldol reactions and demonstrating its versatility by promoting the methanolysis of poly(ethylene terephthalate) (PET) waste. The catalyst was characterized using Fourier-transform infrared spectroscopy (FT-IR), Brunauer-Emmett-Teller (BET) analysis, X-ray powder diffraction (XRD), X-ray fluorescence (XRF), energy dispersive X-ray (EDX) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), and thermal gravimetric analysis (TGA) to decode its chemical composition. The aldol reactions were carried out at ambient temperature in the presence of water as a solvent. PET depolymerization was performed in an autoclave for 1 h using only 6% w/w OPA. The catalyst was recovered and reused in both the reactions for up to four successive cycles with minimal loss in the catalytic activity. The use of OPA as a cost-free, eco-friendly and effective recyclable catalyst enables a greener route for C-C bond formation and PET waste recycling.
