50558-51-5

Upstream product

• 59883-21-5 2,3-bis(hydroxymethyl)-1-phenylnaphthalene 
• 124-38-9 carbon dioxide 
• 3355-31-5 1-chloro-3-phenyl-2-propyne 
• 536-74-3 phenylacetylene 
• 13061-75-1 3-phenylprop-2-yn-1-yl 3-phenylpropiolate 
• 3923-52-2 1,1-diphenyl-2-propyn-1-ol 
• 471-25-0 Propiolic acid 
• 100-52-7 benzaldehyde 
• 57999-77-6 α-phenacylcinnamic acid 
• 4361-96-0 3-benzylidene-5-phenylfuran-2(3H)-one 
• 1985-37-1 4-phenylnaphtho[2,3-c]furan-1,3-dione 
• 21541-60-6 3-phenylprop-2-ynyl 4-methylbenzenesulfonate 
• 584-08-7 potassium carbonate 
• 1794-48-5 1-bromo-3-phenylprop-2-yne 

Relevant academic research and scientific papers

Designing Synergistic Nanocatalysts for Multiple Substrate Activation: Interlattice Ag-Fe3O4 Hybrid Materials for CO2-Inserted Lactones

Multimetallic architectures that combine chemically diverse materials to affect tandem reactions within a single scaffold drive future nanocatalyst development. Here, we show the unique, interlattice growth of the small molecule activating Ag guest within

Development of magnesium oxide-silver hybrid nanocatalysts for synergistic carbon dioxide activation to afford esters and heterocycles at ambient pressure

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.

-Cycloaddition Reactions Using Immobilized Alkynes. A Proof of Concept for an Integral Use of the Outcoming Products in Solid-Phase Synthetic Methodologies

The transition-metal-catalyzed [2 + 2 + 2]-cycloaddition of alkynes has become a powerful atom-economical strategy for aromatic ring construction. Unfortunately, the control of the stereo-, regio-, and chemoselectivity of these processes is usually challenging, and these reactions can potentially lead to complex unuseful mixtures. While solid-phase chemistry has proven to be a successful tool for decreasing the number of cycloadducts formed and for facilitating the purification step, an integral use of the outcoming products in this complex reaction is described herein. By using an immobilized monoalkyne, the transition-metal-catalyzed [2 + 2 + 2]-cycloaddition with soluble 1,6-diyne-esters led to the simultaneous preparation of soluble and solid-supported phthalides, showing a new way to benefit from solid-phase synthetic methodologies.

A 4-high process for the preparation of lactone derivatives

The invention discloses a preparation method of 4-aryltetralin lactone derivatives. The preparation method comprises steps of conducting a reaction between propargyl alcohol and propargylic acid which serve as raw materials at 20-90 DEG C in an organic so

The Total Synthesis of Retrojusticidin B, Justicidin E, and Helioxanthin

Making use of a tandem free radical cyclization process mediated by Mn(OAc)3 as a key operation, the total synthesis of retrojusticidin B, justicidin E, and helioxanthin has been concisely achieved in four or five steps in an overall yield of 4

Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols

Cu/nitroxyl catalysts have been identified that promote highly efficient and selective aerobic oxidative lactonization of diols under mild reaction conditions using ambient air as the oxidant. The chemo- and regioselectivity of the reaction may be tuned by changing the identity of the nitroxyl cocatalyst. A Cu/ABNO catalyst system (ABNO = 9-azabicyclo[3.3.1]nonan-N-oxyl) shows excellent reactivity with symmetrical diols and hindered unsymmetrical diols, whereas a Cu/TEMPO catalyst system (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyl-N-oxyl) displays excellent chemo- and regioselectivity for the oxidation of less hindered unsymmetrical diols. These catalyst systems are compatible with all classes of alcohols (benzylic, allylic, aliphatic), mediate efficient lactonization of 1,4-, 1,5-, and some 1,6-diols, and tolerate diverse functional groups, including alkenes, heterocycles, and other heteroatom-containing groups.

Microwave assisted Perkin reaction for the synthesis of α-arylidine-γ-phenyl-Δ, β, γ-butenolides

Perkin condensation with subsequent intramolecular lactonisation as one pot synthesis of α-arylidine-γ-phenyl-Δ,β,γ- butenolides have been studied under microwave irradiation. The butenolides are cleaved to give keto acids, which are the precursors of pericarbonyl lactone lignans possessing variety of biological activities. Syntheses of butenolides have been carried out using pyridine as a catalyst under microwave conditions. The generality of this protocol has been demonstrated by synthesizing a variety of substituted butenolides in excellent yields, short reaction time and with good purity compared to those under classical thermal conditions. All the products have been characterized by their IR, 1H NMR and UV spectral values.

Regioselective lactonization of unsymmetrical 1,4-diols: An efficient access to lactone lignans

A Cp*Ru-based bifunctional catalyst system (Cp* = η5-C5(CH3)5) with a suitably-designed PN ligand (PN = chelating tertiary phosphine-protic amine ligand) has been developed for a regioselective lactonization of

Advances in the methodology of a multicomponent synthesis of arylnaphthalene lactones

Material and energy inefficiencies in total synthesis can arise from a lack of step economy. Multicomponent syntheses have the potential to optimize step economy and, in turn, to minimize not only waste, but also exposure to hazardous chemicals. Therefore, multicomponent syntheses are of immense interest to the field of Green Chemistry. Herein is described a multicomponent synthesis of arylnaphthalene lignan lactones, which are valuable natural products with promising anticancer and antiviral properties. In an effort to improve our previously reported one-pot, multicomponent synthesis an approach using phenylacetylene, phenylpropargyl chloride, carbon dioxide, catalytic silver iodide, and catalytic 18-crown-6 ether was developed. This methodology was then successfully applied to the preparation of dehydrodimethylconidendrin and its regioisomer, dehydrodimethylretroconidendrin.

Silver-catalyzed one-pot synthesis of arylnaphthalene lactones

(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.