184909-34-0Relevant academic research and scientific papers
Graphene oxide as a recyclable phase transfer catalyst
Kim, Youngmin,Some, Surajit,Lee, Hyoyoung
, p. 5702 - 5704 (2013)
We demonstrated a simple and green chemical method to obtain Michael adducts and their derivatives by using GO as a phase transfer catalyst with different kinds of bases in water and dichloromethane, and we also used GO multiple cycles almost without redu
Synthesis, characterization and catalytic performance in enantioselective reactions by mesoporous silica materials functionalized with chiral thiourea-amine ligand
G?k, Ya?ar,G?k, Halil Zeki
, p. 853 - 874 (2020/11/10)
Chiral heterogeneous catalysts have been synthesized by grafting of silyl derivatives of (1R, 2R)- or (1S, 2S)-1,2-diphenylethane-1,2-diamine on SBA-15 mesoporous support. The mesoporous material SBA-15 and so-prepared chiral heterogeneous catalysts were characterized by a combination of different techniques such as X-ray diffractometry (XRD), Fourier transform infrared (FT-IR), thermogravimetric analysis (TGA), field emission scanning electron microscopy (FESEM), and Brunauer–Emmett–Teller (BET) surface area. Results showed that (1R, 2R)- and (1S, 2S)-1,2-diphenylethane-1,2-diamine were successively immobilized on SBA-15 mesoporous support. Chiral heterogeneous catalysts and their homogenous counterparts were tested in enantioselective transfer hydrogenation of aromatic ketones and enantioselective Michael addition of acetylacetone to β-nitroolefin derivatives. The catalysts demonstrated notably high catalytic conversions (up to 99%) with moderate enantiomeric excess (up to 30% ee) for the heterogeneous enantioselective transfer hydrogenation. The catalytic performances for enantioselective Michael reaction showed excellent activities (up to 99%) with poor enantioselectivities. Particularly, the chiral heterogeneous catalysts could be readily recycled for Michael reaction and reused in three consecutive catalytic experiments with no loss of catalytic efficacies.
Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis
Chahal, Mandeep K.,Payne, Daniel T.,Matsushita, Yoshitaka,Labuta, Jan,Ariga, Katsuhiko,Hill, Jonathan P.
, p. 82 - 90 (2020/01/02)
A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens having increased intramolecular hydrogen-bond donor distances is reported. Oxoporphyrinogens are highly non-planar rigid macrocycles containing a multiple hydrogen bond-forming binding site. In this work, we describe the first example of non-planar OxPs as hydrogen-bond donor catalysts prepared using a molecular engineering approach of the binding site for dual activation of substrates. The introduction of β-substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4-conjugate additions and sulfa-Michael additions, as well as, Henry and aza-Henry reactions at low catalyst loadings (≤ 1 mol-%) under mild conditions. Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi-functional activation of both substrates through hydrogen-bonding interactions.
A nanoporous metal-organic framework as a renewable size-selective hydrogen-bonding catalyst in water
Liu, Yanhong,Ma, Ju,Wu, Pengyan,Zheng, Jia-Jia,Tian, Xueqin,Jiang, Min,He, Yumei,Dong, Han,Wang, Jian
, p. 11855 - 11861 (2019/08/14)
A novel squaramide-containing metal-organic framework (MOF) material has been designed and synthesized. A detailed X-ray crystal structure analysis showed that four squaramides of this MOF adopted two orientations in each dependent nanopore, confirming th
Squaramide-decorated covalent organic framework as a new platform for biomimetic hydrogen-bonding organocatalysis
Li, Xia,Wang, Zhifang,Sun, Jiaxing,Gao, Jia,Zhao, Yu,Cheng, Peng,Aguila, Briana,Ma, Shengqian,Chen, Yao,Zhang, Zhenjie
supporting information, p. 5423 - 5426 (2019/05/16)
A squaramide-decorated COF was synthesized and used as a highly efficient heterogeneous catalyst for hydrogen-bonding organocatalysis as exemplified in the context of catalyzing Michael addition reactions under mild conditions. Our work lays a foundation
Supported and Unsupported Chiral Squaramides as Organocatalysts for Stereoselective Michael Additions: Synthesis of Enantiopure Chromenes and Spirochromanes
Andrés, José M.,Losada, Jorge,Maestro, Alicia,Rodríguez-Ferrer, Patricia,Pedrosa, Rafael
, p. 8444 - 8454 (2017/08/23)
Novel supported chiral bifunctional squaramides have been easily prepared starting from diamines derived from natural amino acids and commercially available aminoalkyl polystyrene resins. These squaramides behave as excellent stereoselective recoverable o
1,3-Diamine-Derived Bifunctional Organocatalyst Prepared from Camphor
Ri?ko, Sebastijan,Svete, Jurij,?tefane, Bogdan,Perdih, Andrej,Golobi?, Amalija,Meden, An?e,Gro?elj, Uro?
supporting information, p. 3786 - 3796 (2016/12/16)
Chiral 1,2-diamines are privileged structural motifs in organocatalysis, whereas efficient 1,3-diamine-derived organocatalysts are very rare. Herein we report a highly efficient camphor-1,3-diamine-derived squaramide organocatalyst. Its catalytic activity
CATALYST FOR ORGANIC REACTION AND METHOD OF USE THEREOF
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Paragraph 0093; 0104-01035, (2015/05/05)
A catalyst for an organic reaction and a method of using a catalyst in an organic reaction are provided. The catalyst for an addition or condensation reaction includes a graphene oxide including an oxygen functional group, and the catalyst is configured t
An expedient and green protocol for the Michael addition of malonates, diketones and p-keto esters to the nitrostyrenes
Agarwal, Jyoti,Naganaboina, Ram Tilak,Peddinli, Rama Krishna
, p. 511 - 518 (2013/06/05)
A novel methodology has been developed for the rapid synthesis of functionalized nitroalkanes by the addition of less reactive carbon nucleophiles such as malonate esters, acetylacetone and ethyl acetoacetate to various r/ms-p-nitrostyrenes under solvent-
Basic-functionalized recyclable ionic liquid catalyst: A solvent-free approach for Michael addition of 1,3-dicarbonyl compounds to nitroalkenes under ultrasound irradiation
Narayanaperumal, Senthil,Da Silva, Rodrigo César,Feu, Karla Santos,De La Torre, Alexander Fernández,Corrêa, Arlene G.,Paix?o, Márcio Weber
, p. 793 - 798 (2013/03/13)
A task-specific ionic liquid (TSIL) has been introduced as a recyclable catalyst in Michael addition. A series of nitroalkenes and various C-based nucleophiles were reacted in the presence of 30 mol% of recyclable basic-functionalized ionic liquid. Good t
