10568-28-2Relevant articles and documents
DFNS/α-CD/Au as a Nanocatalyst for Interpolation of CO2 into Aryl Alkynes Followed by SN2 Coupling with Allylic Chlorides
Wang, Zhiyong,Li, Xuhao,Feng, Li,Liu, Bingzhi,Shamsa, Farzaneh
, p. 1911 - 1922 (2020/11/19)
Abstract: In the present study, to effectively carbonylate cinnamyl chloride and phenylacetylene with CO2, α-cyclodextrin doping dendritic fibrous nanosilica (DFNS) supported nanoparticles of gold was used as a catalyst (DFNS/α-CD/Au NPs). In the catalyst, the nanoparticles of Au were in situ reduced on the surfaces of DFNS. Transmission electron microscopy (TEM), scanning electron microscope (SEM), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), and X-ray energy dispersive spectroscopy (EDS) were utilized for characterizing the nanostructures DFNS/α-CD/Au. It was found that the nanostructures of DFNS/α-CD/Au can be nominated due to their effective and novel catalytic behaviour during the synthesis of 3a,4-dihydronaphtho[2,3-c] furan-1(3H)-ones from cinnamyl chloride, phenylacetylene, and CO2. Graphic Abstract: [Figure not available: see fulltext.].
Development of magnesium oxide-silver hybrid nanocatalysts for synergistic carbon dioxide activation to afford esters and heterocycles at ambient pressure
Gulati, Upasana,Chinna Rajesh,Rawat, Diwan S.,Zaleski, Jeffrey M.
supporting information, p. 3170 - 3177 (2020/06/18)
Multi-metallic hybrid nanocatalysts consisting of a porous metal oxide host and metal satellite guests serve as a scaffold for multi-step transformations of divergent and energy-challenging substrates. Here we have developed a 3D porous MgO framework (Lewis basic host) with Ag0 nanoparticles (noble metal guest) for ambient pressure activation and insertion of CO2 into unsaturated alkyne substrates. The hybrid MgO@Ag-x (x = 2, 5, 7, 8 at% Ag) catalysts are synthesized by impregnating Ag+ ions in porous MgO cubes followed by reduction using NaBH4. Morphological (SEM, TEM, EDX mapping) and structural (PXRD, XPS) characterization reveal that the micron-sized hybrid cubes derive from self-assembly of ～100 nm (edge length) MgO cubes decorated with ～5 to 25 nm Ag0 NPs. Detailed XPS analysis illustrates Ag0 is present in two forms, 2 into aryl alkynes followed by SN2 coupling with allylic chlorides to afford a wide range of ester and lactone heterocycles in excellent yields (61-93%) and with low E-factor (2.8). The proposed mechanism suggests a CO2 capture and substrate assembly role for 3D porous MgO while Ag0 performs the key activation of alkyne and CO2 insertion steps. The catalyst is recyclable (5×) with no significant loss of product yield. Overall, these results demonstrate viable approaches to hybrid catalyst development for challenging conversions such as CO2 utilization in a green and sustainable manner.
Intramolecular dehydro-diels-alder reaction affords selective entry to arylnaphthalene or aryldihydronaphthalene lignans
Kocsis, Laura S.,Brummond, Kay M.
supporting information, p. 4158 - 4161 (2014/09/29)
Intramolecular dehydro-Diels-Alder (DDA) reactions are performed affording arylnaphthalene or aryldihydronaphthalene lactones selectively as determined by choice of reaction solvent. This constitutes the first report of an entirely selective formation of arylnaphthalene lactones utilizing DDA reactions of styrene-ynes. The synthetic utility of the DDA reaction is demonstrated by the synthesis of taiwanin C, retrohelioxanthin, justicidin B, isojusticidin B, and their dihydronaphthalene derivatives. Computational methods for chemical shift assignment are presented that allow for regioisomeric lignans to be distinguished.
Phosphazene base-catalyzed intramolecular cascade reactions of aryl-substituted enynes
Tang, Jian-Sheng,Xie, Ye-Xiang,Wang, Zhi-Qiang,Deng, Chen-Liang,Li, Jin-Heng
experimental part, p. 3204 - 3210 (2010/10/21)
A novel method for the synthesis of 9-aryl-3a,4-dihydronaphtho[2,3-c]furan- 1(3H)-ones has been developed by P4-t-Bu-catalyzed intramolecular cascade reactions of enynes. In the presence of a catalytic amount of phosphazene P4-t-Bu base, a variety of 3-arylallyl 3-arylpropiolates underwent the cascade cyclization reaction smoothly in moderate to excellent yields. Georg Thieme Verlag Stuttgart - New York.
Silver-catalyzed one-pot synthesis of arylnaphthalene lactones
Eghbali, Nicolas,Eddy, Jennifer,Anastas, Paul T.
, p. 6932 - 6935 (2008/12/22)
(Chemical Equation Presented) Arylnaphthalene lignan lactones are valuable natural products with promising anticancer and antiviral properties. In an effort to simplify their synthesis, we investigated a one-pot multicomponent coupling reaction between phenylacetylene, carbon dioxide, and 3-bromo-1-phenyl-1-propyne. After the corresponding 1,6-diyne was generated in situ, cyclization afforded the desired product. The level of regioselectivity was enhanced through the tuning of electronic properties. The use of cinnamyl bromide which led to the formation of a 1,6-enyne intermediate was also studied.
New, short synthesis of arylnaphthofuranone lignans based on reactions of o-aroylbenzyllithiums with furan-2(5H)-one
Kobayashi, Kazuhiro,Tokimatsu, Junsuke,Maeda, Kouji,Morikawa, Osamu,Konishi, Hasatoshi
, p. 3013 - 3016 (2007/10/03)
A simple and general method to prepare 9-arylnaphthofuran-1(3H)-one derivatives has been developed.The reaction of o-aroylbenzyllithiums with furan-2(5H)-one gave the corresponding adducts 5-8 and 5'-7', which upon treatment with thionyl chloride in pyridine followed by dehydrogenation with Pd-C in refluxing p-cymene afforded the arylnaphthofuranone derivatives 13-16.The process proved to be applicable to the preparation of some 1-aryl type naphthofuranone lignans (collinusin, dehydrodimethylretrodendrin and justicidin B).
