62217-45-2

Upstream product

• 13146-23-1 copper(I) phenylacetylenide 
• 94957-42-3 n-hexynyl(phenyl)iodonium tosylate 
• 138583-91-2 dilithium di(phenylethynyl)cyanocuprate 
• 1119-67-1 1-iodo-1-hexyne 
• 536-74-3 phenylacetylene 
• 3757-88-8 tributylstannylethynylbenzene 
• 693-02-7 hex-1-yne 
• 7299-58-3 phenylpropiolyl chloride 
• 1972-97-0 2-heptynoic acid chloride 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 1120-29-2 5,7-dodecadiyne 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 1377861-19-2 1-[2-(n-butyl)ethynyl]-1,2-benziodoxol-3(1H)-one 

Downstream Products

• 1629909-55-2 C₃₀H₂₆ 
• 1233187-78-4 C₂₀H₂₀ 

Relevant academic research and scientific papers

Transition metal-free coupling of terminal alkynes and hypervalent iodine-based alkyne-transfer reagents to access unsymmetrical 1,3-diynes

A variety of unsymmetrical 1,3-diynes can easily be accessed in good yields under catalyst- and transition metal-free conditions by reacting terminal alkynes with hypervalent iodine-based electrophilic alkyne-transfer reagents.

Gold-Catalyzed Cadiot–Chodkiewicz-type Cross-Coupling of Terminal Alkynes with Alkynyl Hypervalent Iodine Reagents: Highly Selective Synthesis of Unsymmetrical 1,3-Diynes

A new and efficient method for the synthesis of unsymmetrical 1,3-butadiynes by gold-catalyzed C(sp)–C(sp) cross-coupling of terminal alkynes with alkynyl hypervalent iodine(III) reagents has been developed. The reaction features high selectivity and efficiency, mild reaction conditions, wide substrate scope, and functional-group compatibility, and is a highly attractive complement to existing methods. Mechanistic studies reveal that formation of a phenanthrolinyl-ligated gold(I) complex is crucial for the efficiency and selectivity of the target transformation.

Facile Synthesis of Surface-Clean Monodispersed CuOx Nanoparticles and Their Catalytic Properties for Oxidative Coupling of Alkynes

We show a facile method to prepare surface-clean monodispersed small and stable CuOx nanoparticles with controllable average sizes from below 1 nm up to ～5 nm without using bulk capping agent. Structural and surface characterizations show that the chemica

Formal [4+ 2] reaction between 1,3-diynes and pyrroles: Gold(I)-catalyzed indole synthesis by double hydroarylation

Indole synthesis by a gold(I)-catalyzed intermolecular formal [4+2] reaction between 1,3-diynes and pyrroles has been developed. This reaction involves the hydroarylation of 1,3-diynes with pyrroles followed by an intramolecular hydroarylation to give the 4,7-disubstituted indoles. This reaction can also be applied to the synthesis of carbazoles when indoles are used as the nucleophiles instead of pyrroles.

Facile synthesis of 3, 3′-disubstituted 2, 2′-binaphthyls by transition-metal-catalyzed double benzannulation

3, 3′-Disubstituted 2, 2′-binaphthyls were prepared by the Cuor Re-catalyzed double benzannulation reaction of 2-(phenylethynyl) benzaldehyde with various butadiynes in the presence of trichloroacetic acid, in moderate to good yields. Acceleration of the second benzannulation was clearly observed.

Synthesis of unsymmetrical 1,3-diynes via alkyne cross-metathesis

The tungsten benzylidyne complex [PhC≡W{OSi(OtBu)3} 3] (1) efficiently catalyses the metathetic conversion between symmetrical and unsymmetrical 1,3-diynes, which provides the opportunity to prepare the latter species directly from terminal alkynes by a combination of copper-catalysed homocoupling and catalytic alkyne cross-metathesis (ACM).

Coupling of terminal alkynes promoted by organic polyvalent iodine compounds

Terminal alkynes couple smoothly in the presence of PhI(OAc)2 or PhI(OH)OTs, catalytic amount of CuI and base, affording conjugated diynes.

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.

Palladium-catalysed cross-coupling reactions of aryl-, alkenyl- and alkynyl-iodonium salts and iodanes with terminal alkynes in aqueous medium

The ligand-free Pd(OAc)2-catalysed coupling reaction of aryl-, alkenyl- and alkynyl-iodonium tetrafluoroborate and iodanes with terminal alkynes proceeds readily in the presence of NaHCO3 in aqueous medium to afford the substituted alkynes in high yields under mild conditions.

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 8. Preparation of symmetrical and unsymmetrical 1,3-diynes from alkynoyl ylides and oxalyl diylides

Seven examples of the alkynoyl phosphorus ylides 5 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 750°C, to undergo extrusion of Ph3PO to give the unsymmetrical 1,3-diynes 9 in moderate yield. Six examples of the oxalyl diylides 6 have been prepared and their fully assigned 13C NMR spectra are presented. Upon FVP, those with R = aryl undergo two-fold extrusion of Ph3PO to give symmetrical 1,3-diynes 13 but this requires the unusually severe temperature of 900°C. In contrast those with R = CO2Me, CO2Et or COPh undergo complete reaction at 500°C but afford only Ph3PO and fragmentation products.