214898-04-1

Upstream product

• 627-19-0 1-Pentyne 
• 696-62-8 para-iodoanisole 
• 764-33-0 hex-2-ynoic acid 
• 768-60-5 4-methoxyphenylacetylen 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 178056-76-3 4-(pent-1-yn-1-yl)phenol 
• 7642-16-2 (Z)-1-methoxy-4-(pent-1-en-1-yl)benzene 
• 1616927-23-1 5-phenyl-6-propyl-2,3-dihydro-1H-indene 
• 1616927-27-5 5-(4-methoxyphenyl)-6-propyl-2,3-dihydro-1H-indene 

Relevant academic research and scientific papers

Cu2O Nanocrystals-Catalyzed Photoredox Sonogashira Coupling of Terminal Alkynes and Arylhalides Enhanced by CO2

Herein the first visible-light-activated Sonogashira C?C coupling reaction at room temperature catalyzed by single-metal heterogeneous Cu2O truncated nanocubes (Cu2O TNCs) was developed. A wide variety of aryl halides and terminal alkynes worked well in this recyclable heterogeneous photochemical process to form the corresponding Sonogashira C?C coupling products in good yields. Mechanistic control studies indicated that CO2 enhances the formation of light-absorbing heterogeneous surface-bound CuI-phenylacetylide (λmax=472 nm), which further undergoes single-electron transfer with aryl iodides/bromides to enable Sonogashira Csp2 ?Csp bond formation. In contrast to literature-reported bimetallic TiO2-containing nanoparticles as photocatalyst, this work avoided the need of cocatalysis by TiO2. Single-metal CuI in Cu2O TNCs was solely responsible for the observed Csp2 ?Csp coupling reactions under CO2 atmosphere.

A Sustainable, User-Friendly Protocol for the Pd-Free Sonogashira Coupling Reaction

We herein present a new catalytic system for the palladium-free Sonogashira coupling reaction. The catalytically active moiety is formed in situ, in a straightforward and user-friendly manner, by combining a widely available low-cost copper salt and an N-

Multi-Metal-Catalyzed Oxidative Radical Alkynylation with Terminal Alkynes: A New Strategy for C(sp3)-C(sp) Bond Formation

A new way for C(sp3)-C(sp) cross-coupling with terminal alkynes has been developed by using a multi-metal-catalyzed reaction strategy. Alkyl radicals generated from different approaches are able to couple with terminal alkynes by judicious selection of the catalyst combination. This reaction protocol offers an efficient alternative approach for the synthesis of substituted alkynes from terminal alkynes besides traditional Sonogashira coupling. Mechanistic studies have also been carried out to clarify the role of each metal catalyst in the radical alkynylation processes. The reactions were found to go through radical reaction pathways. Synergistic cooperation of the metal catalysts is the key for controlling the reaction selectivity of alkyl radicals toward C(sp3)-C(sp) bond formation.

Facile Light-Mediated Preparation of Small Polymer-Coated Palladium-Nanoparticles and Their Application as Catalysts for Alkyne Semi-Hydrogenation

A facile light-mediated preparation of small palladium nanoparticles (PdNPs) with a diameter of 1.3 nm and low dispersity by using low-priced and readily prepared photoactive polymers is presented. These polymers act as reagents for the photochemical reduction of Pd ions and they are also stabilizers for the PdNPs generated in situ. The PdNP–polymer hybrid materials prepared by this reliable approach are efficient hydrogenation catalysts that show high activity and Z-selectivity in the semi-hydrogenation of alkynes. These PdNP–catalyst hybrid materials can be readily recycled and reused up to five times.

Palladium and copper catalyzed Sonogashira decarboxylative coupling of aryl iodides and alkynyl carboxylic acids

A mild procedure of palladium and copper catalyzed decarboxylative cross-coupling reaction of aryl halides and alkynyl carboxylic acids has been developed. Low molecular weight acids, to introduce small building blocks, were specifically used. This method

Ti(OiPr)4/nBuLi: An attractive reagent system for [2+2+2] cyclotrimerisation reactions

A convenient method for the [2+2+2] cyclotrimerisation of alkynes using Ti(OiPr)4/nBuLi is presented. Homotrimerisation of arylacetylenes proceeds within minutes with excellent regioselectivity. Moreover, the intermolecular construction of ABB heterotrimers can be achieved selectively from two different alkynes with similar electronic properties. The method is also suitable for the synthesis of pyridines.

Copper-catalyzed carboarylation of alkynes via vinyl cations

Copper-catalyzed arylation of electron rich alkynes reveals stabilized trisubstituted vinyl cation equivalents that react with pendant arene nucleophiles to form all carbon tetrasubstituted alkenes. The new process streamlines the synthesis of important medicinally relevant molecules.

Functionalization of Csp3-H and Csp 2-H bonds: Synthesis of spiroindenes by enolate-directed ruthenium-catalyzed oxidative annulation of alkynes with 2-aryl-1,3-dicarbonyl compounds

Ru(de) awakening: The synthesis of carbocycles by the ruthenium-catalyzed oxidative annulation of alkynes with 2-aryl cyclic 1,3-dicarbonyl substrates is described. Proceeding by the functionalization of C sp 3-H and C sp 2-H bonds, and the formation of an all-carbon quaternary center, the reaction provides a diverse range of spiroindenes in good yields with high levels of regioselectivity. Copyright

Palladium-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with arylboronic acids

A highly efficient and mild palladium-catalyzed decarboxylative cross-coupling of aryl boronic acids and alkynyl carboxylic acids for the synthesis of unsymmetrical substituted alkynes is described for the first time.

4-Alkynylphenyl imidazolylpropyl ethers as selective histamine H3- receptor antagonists with high oral central nervous system activity

In search for potent and therapeutically useful H3-receptor antagonists, we prepared novel 4-alkynylphenyl ether derivatives of 3-(1H- imidazol-4-yl)propanol in a convenient synthetic route. All compounds were tested for in vitro and in vivo H