35133-77-8

Upstream product

• 617-90-3 2-furancarbonitrile 
• 536-74-3 phenylacetylene 
• 54829-48-0 2-iodofuran 
• 13331-23-2 fur-2-ylboronic acid 
• 100-44-7 benzyl chloride 
• 98-01-1 furfural 
• 4706-43-8 1-benzyl-1H-benzotriazole 
• 31174-04-6 furan-2-carbonyl fluoride 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 603-33-8 triphenylbismuthane 
• 105797-57-7 1-butylseleno-2-phenylacetylene 
• 81745-86-0 2-furylzinc chloride 
• 100074-10-0 2,2-dibromovinyl-2-furan 
• 98-80-6 phenylboronic acid 

Downstream Products

• 1202-49-9 (E)-2-styrylfuran 
• 86358-28-3 1-(furan-2-yl)-2-phenyl-ethane-1,2-dione 
• 14385-45-6 5-phenylethinyl-2-furancarboxaldehyde 

Relevant academic research and scientific papers

Copper-catalyzed cross-coupling of 1-iodoalkynes with organostannanes

Copper-catalyzed cross-coupling of 1-iodoalkynes with organostannanes was readily achieved in the presence of CuI (10 mol%) in DMF at room temperature for 6 hours by adding 1-iodoalkynes slowly to organostannanes.

Simple and efficient diaryl alkyne synthesis method

The embodiment of the invention discloses a simple and efficient diaryl alkyne synthesis method. The method comprises the steps of by taking arylmethylbenzotriazole and aromatic aldehyde as raw materials, carrying out addition and double-beta-elimination reaction under the action of bis (trimethylsilyl) amino salt MN (SiMe3) 2 to synthesize diaryl alkyne by a one-pot method. The raw materials and chemical reagents used in the method are easy to obtain, the reaction conditions are mild, the operation is simple, the substrate universality is good, the product yield is high, and the method is a simple and efficient diaryl alkyne synthesis method.

Facile one-pot synthesis of diarylacetylenes from arylaldehydes: Via an addition-double elimination process

A practical one-pot protocol has been developed to synthesize diarylacetylenes from arylaldehydes by treatment with 1-(arylmethyl)benzotriazoles and LiN(SiMe3)2. The reaction proceeded through imine formation, Mannich-type addition and double elimination to deliver products in up to 99% yields with broad substrate scope. In addition, gram-scale synthesis of 1-bromo-4-(phenylethynyl)benzene has been demonstrated.

Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes: Synthesis of unsymmetrical diarylethynes

Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes is described. This reaction not only effectively inhibits the formation of undesired homocoupled products by avoiding the addition of a base, but also exhibits a wide substrate scope to provide a general access to diverse unsymmetrical diarylethynes.

Sustainable dipolar homo-dicopper (II) dihydrazone complex as a catalyst for Sonogashira cross couplings

A novel dicopper (II) complex, Cu2L, was prepared form the complexation of the new polydentate ligand (H4L), bis(sodium 3-formyl-4-hydroxybenzenesulfonate)succinylhydrazone, with copper acetate. The novel homobinuclear complex was quite characterized by various physico-chemical tools and employed as a homogeneous and efficient-green catalyst for Sonogashira cross-couplings of phenylacetylene with halobenzenes under sustainable conditions. Cu2L exhibited very good catalytic performance with excellent chemoselectivity. The catalytic efficiency of Cu2L was improved by using ionic liquids–aqueous media (1: 1, binary mixture). A mechanistic pathway was also proposed for Cu(II)-catalyzed Sonogashira cross-coupling reactions for the reported finding. DFT for H4L and Cu2L were studied. Electronic configurations, energy of HOMO and LUMO orbitals, energy gap between orbitals (ΔE), electronegativity, hardness and softness were also calculated and compared with the applicable catalytic findings of Cu2L, which are in good conformity.

Synthesis of Internal Alkynes through an Effective Tandem Elimination-Hydrodebromination-Cross-Coupling of gem-Dibromoalkenes with Halobenzenes

Carbon-carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C-C cross-coupling reaction of two kinds of organic halide, a gem -dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination-hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.

Cross-coupling reactivity of 1,1-dichloroalkenes under palladium catalysis: Domino synthesis of diarylalkynes

An efficient synthesis of diarylalkynes was achieved from the domino cross-coupling reaction of 1,1-dichloroalkenes with triarylbismuth reagents under palladium-catalyzed conditions. Under the established palladium protocol, 1,1-dichloroalkenes demonstrated hitherto unknown remarkable cross-coupling reactivity with organometallic triarylbismuth reagents to furnish functionalized diarylalkynes.

Application of organoselenides in the Suzuki, Negishi, Sonogashira and Kumada cross-coupling reactions

We reported herein the regio- and stereoselective palladium-catalyzed cross-coupling reactions of unsaturated organoselenides with Sonogashira, Suzuki, Negishi and Kumada partners. The reactions were in general carried out with Pd(PPh3)4 (10 mol%), in DMF at 80 °C to afford the cross-coupling products in good yields. This strategy tolerated a wide range of substrates, such as alkynyl, vinyl, aryl and heteroaryl selenides with a variety of sensitive functional groups and gave the cross-coupling products in good yields.

Rh-catalyzed decarbonylation of conjugated ynones via carbon-alkyne bond activation: Reaction scope and mechanistic exploration via DFT calculations

In this full article, detailed development of a catalytic decarbonylation of conjugated monoynones to synthesize disubstituted alkynes is described. The reaction scope and limitation has been thoroughly investigated, and a broad range of functional groups

Palladium-catalyzed regioselective allylation of five-membered heteroarenes with allyltributylstannane

Palladium-catalyzed allylation reactions of 2-(chloromethyl)thiophenes, 2-(chloromethyl)furans, and N-protected 2-(chloromethyl)-1H-pyrroles with allyltributylstannane were described in this study. This type of allylation reaction regioselectively occurred on the heteroarene rings to produce allylated dearomatization products or allylated heteroarenes with satisfactory yields.