16900-79-1

Upstream product

• 932-87-6 1-Bromo-2-phenylacetylene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 2063-19-6 4-bromo-2-methylbut-3-yn-2-ol 
• 536-74-3 phenylacetylene 
• 763-12-2 2-methyl-3,5-hexadiyn-2-ol 
• 591-50-4 iodobenzene 
• 932-88-7 1-iodo-2-phenylethyne 
• 13146-23-1 copper(I) phenylacetylenide 
• 1483-82-5 phenylethynyl chloride 
• 98-86-2 acetophenone 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 105797-57-7 1-butylseleno-2-phenylacetylene 
• 100-63-0 phenylhydrazine 

Downstream Products

• 91735-12-5 1,1,5-Triphenyl-2,4-pentadiin-1-ol 
• 5701-81-5 buta-1,3-diynylbenzene 
• 117635-47-9 2-(phenylbuta-1,3-diyn-1-yl)pyridine 
• 117635-50-4 2-(4-Phenyl-buta-1,3-diynyl)-quinoline 
• 117635-49-1 2-(4-Phenyl-buta-1,3-diynyl)-benzothiazole 
• 85523-37-1 3-phenylthio-2-methyl-6-phenyl-3-hexen-5-yn-2-ol 
• 77785-42-3 3-ethylthio-2-methyl-6-phenyl-3-hexen-5-yn-2-ol 
• 171667-57-5 (Z)-1-(butyltelluro)-4-phenylbut-1-en-3-yne 
• 950894-45-8 2-phenyl-3-iodo-5-(α-hydroxy-α,α-dimethyl)methylselenophene 
• 20264-56-6 1,6-diphenyl-1,3,5-hexatriyne 
• 120517-41-1 diethyl 4-(phenylbutadiynyl)-2,6-pyridinedicarboxylate 

Relevant academic research and scientific papers

AgOTf-catalyzed electrophilic cyclization of triynols with NXS: Rapid synthesis of densely trisubstituted naphthalenes and quinolines

A silver triflate-catalyzed electrophilic cyclization reaction of acyclic triynols with NXS (X=I, Br) under mild conditions is reported. Three reactive functional groups, such as a carbonyl group, an alkyne group, and a halogen, could be selectively installed at the C1, C2, and C3 positions to obtain the naphthalene and quinoline products, respectively. The obtained densely trisubstituted products could be further transformed into more complex aromatic products by manipulating the alkynyl moiety and the other two functional groups as synthons. Copyright

Synthesis of (Z)-1-phenylseleno-1,4-diorganyl-1-buten-3-ynes: Hydroselenation of symmetrical and unsymmetrical 1,4-diorganyl-1,3-butadiynes

The hydroselenation of 1-organyl-1,3-butadiynes and 1,4-diorganyl-1,3-butadiynes with the sodium phenylselenolate anion, which was generated in situ by reacting diphenyl diselenide with NaBH4 in aqueous ethanol, results in the regio-, stereo- and chemoselective formation the 1-phenylseleno-4-organyl-1-buten-3-ynes and 1-phenylseleno-1,4-diorganyl-1-buten-3-ynes of Z configuration respectively. The lack of selectivity with the 2-hydroxy-2-methyl-3,5-dodecadiyne was observed and the obtained product structures were studied in detail.

In Situ Synthesis of CuN4/Mesoporous N-Doped Carbon for Selective Oxidative Crosscoupling of Terminal Alkynes under Mild Conditions

The 1,3-conjugated diynes are an important class of chemical intermediates, and the selective crosscoupling of terminal alkynes is an efficient chemical process for manufacturing asymmetrical 1,3-conjugated diynes. However, it often occurs in homogenous conditions and costs a lot for reaction treatment. Herein, a copper catalyzed strategy is used to synthesize highly ordered mesoporous nitrogen-doped carbon material (OMNC), and the copper species is in situ transformed into the copper single-atom site with four nitrogen coordination (CuN4). These features make the CuN4/OMNC catalyst efficient for selective oxidative crosscoupling of terminal alkynes, and a wide range of asymmetrical and symmetrical 1,3-diynes (26 examples) under mild conditions (40?°C) and low substrates ratio (1.3). Density functional theory (DFT) calculations reveal that the aryl–alkyl crosscoupling has the lowest energy barrier on the CuN4 site, which can explain the high selectivity. In addition, the catalyst can be separated and reused by simply centrifugation or filtration. This work can open a facile avenue for constructing single-atom loaded mesoporous materials to bridge homogeneous and heterogeneous catalysis.

Tuning of cross-Glaser products mediated by substrate-catalyst polymeric backbone interactions

Tuning of cross-Glaser products using different polymeric backbones supported by copper oxide nano-catalysts has been demonstrated by tweaking the substrate-catalyst interactions under greener conditions. Further, highly reactive magnetically separable and recyclable catalyst with scalability is demonstrated.

Rh(III)-Catalyzed [3 + 2] Spirocyclization of 2 H-Imidazoles with 1,3-Diynes for the Synthesis of Spiro-[imidazole-indene] Derivatives

An effective strategy to synthesize spirocyclic compounds, [imidazole-4,1′-indene], has been efficaciously developed relied on Rh(III)-catalyzed [3 + 2] spirocyclization of 2H-imidazoles and 1,3-diynes with excellent chemselectivity and regioselectivity.

A new type of carborane-based electron-accepting material

In this study, a new type of carborane-based electron acceptor was prepared by the direct attachment of an ethynyl group to the carboranyl carbon atom. Analyses of photophysical and electrochemical and DFT calculations suggested that the direct attachment of the ethynl group significantly affects the electrochemical properties of these o-carborane systems. This journal is

Copper Nanoparticles on Ordered Mesoporous Carbon Nitride Support: a Superior Catalyst for Homo- and Cross-Coupling of Terminal Alkynes under Base-Free Conditions

A novel ordered mesoporous carbon nitride (OMCN) was synthesized as a functionalized support with 2,4,6-trichloro-1,3,5-triazine and benzidine as starting materials in the presence of SBA-15 as a template. Copper nanoparticles were then loaded on the C–N material to achieve a novel nanocomposite catalyst (Cu NPs-OMCN). The nanocomposite was utilized as a highly efficient catalyst for homo- and cross-coupling of terminal alkynes under base-free conditions in ethanol, and various symmetrical and unsymmetrical 1,3-diynes were obtained with good to excellent yields. Moreover, based on this reaction, a one-pot approach to synthesize 2,5-disubstituted thiophenes and furans from terminal alkynes were developed. Furthermore, the heterogeneous catalyst could be recovered and reused conveniently for several times with satisfactory yields.

Metallomicelle catalyzed aerobic tandem desilylation/Glaser reaction in water

PEG-grafted nitrogen ligands were synthesized. The corresponding copper complexes serve as metallomicellar nanoreactors for the aerobic tandem desilylation/Glaser coupling of TMS-protected alkynes in water. The protocol is also suitable for base-free homocoupling of terminal alkynes. The metallomicellar catalyst could be recycled 5 times with minor loss of reactivity.

One-pot synthesis of unsymmetrical 1,3-butadiyne derivatives and their application in the synthesis of unsymmetrical 2,5-diarylthiophenes

A one-pot protocol was developed for the synthesis of unsymmetrical 1,3-butadiynes. The procedure is based on two sequential reactions: deprotection of R–C≡C–C≡C– C(Me)2OH derivatives in a retro-Favorskii reaction to furnish a terminal 1,3-butadiyne compound, which reacted with aryl iod-ides in a Sonogashira-type cross-coupling reaction catalyzed by Pd(PPh3)4 and CuI, using TBAOH as activator and toluene as solvent under reflux for 10 min. We also studied in situ thiocycli-zation of 1,3-butadiynes, leading to unsymmetrical 2,5-diaryl-thiophenes. The principal features of this method are operational simplicity, good substrate scope, very fast reaction, and high yields.

Transition-Metal-Free Synthesis of Borylated Thiophenes via Formal Thioboration

A simple, regiocontrolled, and transition-metal-free approach to access exclusively 3-borylated thiophene derivatives is reported. The commercially available B-chlorocatecholborane reagent (ClBcat) acts as a carbophilic Lewis acid to activate the alkyne i