123439-12-3Relevant academic research and scientific papers
N-(4-[2.2]paracyclophanyl)-2′-hydroxyacetophenone imine: An effective paracyclophane Schiff-base ligand for use in catalytic asymmetric cyclopropanation reactions
Masterson, Douglas S.,Shirley, Caitlyne,Glatzhofer, Daniel T.
, p. 111 - 115 (2012)
The synthesis of planar chiral N-(4-[2.2]paracyclophanyl)-2′- hydroxyacetophenone imine (5) and its use as a ligand for the copper(II) catalyzed cyclopropanation of styrene and stilbene derivatives using diazoesters is presented. Catalyst loadings of 0.1
Diversity-Oriented Synthesis of [2.2]Paracyclophane-derived Fused Imidazo[1,2-a]heterocycles by Groebke-Blackburn-Bienaymé Reaction: Accessing Cyclophanyl Imidazole Ligands Library
Stahlberger, Mareen,Schwarz, Noah,Zippel, Christoph,Hohmann, Jens,Nieger, Martin,Hassan, Zahid,Br?se, Stefan
, (2021/12/13)
This report describes the synthesis of a [2.2]paracyclophane-derived annulated 3-amino-imidazole ligand library through a Groebke-Blackburn-Bienaymé three-component reaction (GBB-3CR) approach employing formyl-cyclophanes in combination with diverse aliphatic and aromatic isocyanides and heteroaromatic amidines. The GBB-3CR process gives access to skeletally-diverse cyclophanyl imidazole ligands, namely 3-amino-imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrazines. Additionally, a one-pot protocol for the GBB-3CR by an in situ generation of cyclophanyl isocyanide is demonstrated. The products were analyzed by detailed spectroscopic techniques, and the cyclophanyl imidazo[1,2-a]pyridine was confirmed unambiguously by single-crystal X-Ray crystallography. The cyclophanyl imidazole ligands can be readily transformed to showcase their useful utility in preparing N,C-palladacycles through regioselective ortho-palladation.
Para-Functionalization of N-Substituted 4-amino[2.2]paracyclophanes by Regioselective Formylation
Felder, Simon,Micouin, Laurent,Benedetti, Erica
, p. 4015 - 4018 (2021/05/03)
Herein, we report a simple and convenient procedure to prepare para-disubstituted [2.2]paracyclophanes in a straightforward manner. Our approach relies on a regioselective formylation of N-substituted 4-amino[2.2]paracyclophanes, which allows an easy access to a series of products incorporating a reactive aldehyde function para to the electron-donating group. These compounds can be engaged in a variety of orthogonal late-stage derivatization processes involving either the carbonyl group or the amine function, and can serve as precursors to rapidly access more complex paracyclophane derivatives. Control of planar chirality is also possible by performing a kinetic resolution of key racemic intermediates through asymmetric transfer hydrogenation. The formylation can be run on a synthetically useful scale, thus confirming the practical applicability of our method.
Chiral fluorescent compound based on cyclophane skeleton and preparation method and application thereof
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Paragraph 0109-0113, (2019/09/14)
The invention relates to a chiral fluorescent compound based on a cyclophane skeleton and a preparation method and application thereof. According to the invention, the cyclophane rigid skeleton structure is utilized, so that the chirality of the cyclophane can be well maintained in an excitation state, and thus high luminous efficiency and good circularly polarized luminous performance (high asymmetry factor) are obtained. The light emission wavelength, circular polarized light emission (CPL) intensity and luminous intensity can be adjusted and controlled by changing R1 and R2 substituents. Bychanging a R3 substituent, molecules are in the state of electron donor/electron acceptor, and a thermally activated delayed fluorescent material can be obtained.
A Parylene A precursor synthesis method (by machine translation)
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Paragraph 0027; 0035-0042; 0049-0068, (2018/10/19)
The invention discloses a Parylene A precursor synthesis method, comprises the following steps: (1) to [2, 2] - to di-methyl benzene ring b body as raw materials through the nitration reaction to obtain the intermediate product 4 - nitro - [2, 2] - dimethyl benzene ring to the second body; (2) the intermediate product 4 - nitro - [2, 2] - dimethyl benzene ring on the second body is arranged in the reactor into the hydrogen in the hydrogenation catalyst under the action of the reduction reaction, to get the crude product, concentrated, recrystallization, dried to obtain 4 - amino - [2, 2] - dimethyl benzene ring on the second body. The mild reaction conditions of the method, the resulting product yield and purity are relatively high, the catalyst and the solvent can be recycled, is suitable for mass production. (by machine translation)
Planar-Chiral [2.2]Paracyclophane-Based Amides as Proligands for Titanium- and Zirconium-Catalyzed Hydroamination
Braun, Carolin,Br?se, Stefan,Schafer, Laurel L.
, p. 1760 - 1764 (2017/04/13)
A synthetic route to racemic and enantiopure planar chiral [2.2]paracyclophanes with amide groups was developed to combine the well-established reactivity of amides as N,O-chelating ligands in hydroamination reactions with the planar chirality of the [2.2
[2.2]Paracyclophanes with N-Heterocycles as Ligands for Mono- and Dinuclear Ruthenium(II) Complexes
Braun, Carolin,Nieger, Martin,Thiel, Werner R.,Br?se, Stefan
, p. 15474 - 15483 (2017/11/09)
[2.2]Paracyclophane, with its unique structure, allows the design of unusual 3D structures by functionalization of this rigid and stable hydrocarbon scaffold. Therefore different mono- and homodisubstituted [2.2]paracyclophanes with pyridyl, pyrimidyl and oxazolinyl substituents were developed in order to evaluate their ability as bridging ligands for two ruthenium centres. With the successfully synthesized [2.2]paracyclophane-based N-donor functions, the cycloruthenation reaction using [RuCl2(p-cymene)]2 as precursor was explored. Compared to 2-phenylpyridine, the [2.2]paracyclophane derivative is clearly inferior in the cycloruthenation reaction, resulting in poor yields for the neutral complexes. By addition of KPF6, the cationic complexes can be obtained in good yields and are formed diastereoselectively in case of a pyridyl substituent, resulting in only one diastereomer for dinuclear ruthenium complexes of bispyridyl-substituted [2.2]paracyclophanes as bridging ligands.
The synthesis of substituted amino[2.2]paracyclophanes
Jayasundera, Krishanthi P.,Kusmus, Disra?li N. M.,Deuilhé, Lise,Etheridge, Leonie,Farrow, Zane,Lun, David J.,Kaur, Gurpreet,Rowlands, Gareth J.
, p. 10848 - 10860 (2016/12/06)
Two methodologies for the formation of substituted amino[2.2]paracyclophane derivatives were developed. The first involves the direct amination of bromo[2.2]paracyclophanes with sodium azide. This permits the synthesis of simple mono- and disubstituted de
[2-2]PARACYCLOPHANE-DERIVED DONOR/ACCEPTOR-TYPE MOLECULES FOR OLED APPLICATIONS
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, (2016/12/22)
Disclosed are [2.2]paracyclophane-derivative compounds and related polymers that are useful as stable, efficient, blue-light emitting compounds for OLED applications.
Synthesis of planar chiral [2.2]Paracyclophanyl imidazo[1,5-a[pyridinium salts for the rhodium-catalyzed asymmetric arylation
Wang, Dengxia,Ma, Yudao,He, Fuyan,Duan, Wenzeng,Zhao, Lei,Song, Chun
, p. 810 - 825 (2013/02/25)
Several novel flexibility-restricted imidazo[1,5-a]pyridinium triflates (abbreviated as imidazolium salts) were synthesized from (4S p,13R p)-()-4-amino-13-bromo[2.2]paracyclophane and pyridylaldehyde. These imidazolium salts can be used as nitrogen-containing heterocyclic carbene precursors in asymmetric catalysis and here they are applied in the Rh-catalyzed asymmetric 1,2-addition of arylboronic acids to aldehydes. After optimizing the catalytic situations and testing a series of substrates, moderate enantioselectivity and good yield were obtained.
