157729-39-0

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 75867-40-2 4-[2-(trimethylsilyl)ethynyl]benzonitrile 
• 3032-92-6 4-cyanophenylacetylene 
• 105-07-7 4-cyanobenzaldehyde 
• 131356-52-0 2,2-dibromo-1-(4-cyanophenyl)ethene 

Downstream Products

• 246247-33-6 1,3,5-tris(4-butadiynylbenzonitrile)benzene 
• 1206482-99-6 4-(5-phenyl-oxazol-2-ylethynyl)-benzonitrile 
• 1021176-20-4 4-[(2-bromophenyl)ethynyl]benzonitrile 
• 1211318-69-2 2'-bromo-2-[(4-cyanophenyl)ethynyl]biphenyl 
• 1228672-43-2 4-(2-((S)-4-isopropyl-2-oxooxazolidin-3-yl)ethynyl)benzonitrile 
• 1285537-25-8 4-((trans-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)ethynyl)benzonitrile 
• 1285537-18-9 4-((trans-4-(tert-butyl)cyclohexyl)ethynyl)benzonitrile 
• 1379658-15-7 4-(benzo[d]oxazole-2-carbonyl)benzonitrile 
• 1352658-10-6 1-bromo-2-[5-(4-cyanophenyl)pent-4-ynyloxy]benzene 
• 1352658-02-6 1-bromo-2-[6-(4-cyanophenyl)hex-5-ynyloxy]benzene 
• 62856-06-8 4-[2-(4-methylphenyl)ethynyl]benzonitrile 
• 1422721-71-8 (E)-N-benzyl-N-(2-(4-cyanophenyl)-1-iodovinyl)-4-methylbenzenesulfonamide 
• 1422721-72-9 (E)-N-benzyl-N-(1-bromo-2-(4-cyanophenyl)vinyl)-4-methylbenzenesulfonamide 
• 1432655-48-5 methyl 1-((4-cyanophenyl)ethynyl)-1H-indole-3-carboxylate 

Relevant academic research and scientific papers

Chloramine Salt Mediated Oxidative Halogenation of Terminal Alkynes with KI or NaBr: Practical Synthesis of 1-Bromoalkynes and 1-Iodoalkynes

A direct oxidative halogenation of terminal alkynes has been realized using chloramine-B as the oxidant and KI or NaBr as the halogen source. This reaction enables a general and practical access to synthetically valuable 1-bromoalkynes and 1-iodoalkynes i

DBU/DMSO Promoted Dehydrobromination of 1,1-Dibromoolefins. A General Synthesis of 1-Bromoaromatic Alkynes under mild Conditions

A new procedure for the synthesis of 1-bromoalkynes by DMSO/DBU induced dehydrobromination of 1,1-dibromoethylenes under mild conditions is described.

Palladium-Catalyzed Carbonylation in the Synthesis of N-Ynonylsulfoximines

Palladium-catalyzed carbonylation reactions with Cr(CO)6 as carbonyl source are key for the preparation of N-ynonylsulfoximines from NH-sulfoximines and bromoalkynes. The couplings proceed at room temperature with a wide range of substrate combinations affording the corresponding products in good yields. (Figure presented.).

Nickel-Catalyzed Reductive 1,2-Dialkynylation of Alkenes Bearing an 8-Aminoquinoline Directing Group

An unprecedented nickel-catalyzed reductive 1,2-dialkynylation of alkenes bearing an 8-aminoquinoline directing group has been developed. This method proceeded through a migratory insertion/reductive-coupling process under mild conditions with a wide substrate scope and good functional group tolerance, providing direct access to the synthetically flexible 1,5-diynes. Moreover, the 1,2-dialkynylation products could be further converted to borate-ester- or azide-functionalized 1,5-dienes, ditriazole, β-diyne primary amide, and trisubstituted benzene.

Controlled Reactivity of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Selective Synthesis of 1-(Bromoethynyl)arenes

The nucleophilic reactivity of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was completely controlled by the formation of monohydrate (DBU?H2O) in the synthesis of 1-(bromoethynyl)arenes from 1,1-dibromoalkenes. Differential reactivity of DBU in pr

Highly efficient and recyclable catalyst for the direct chlorination, bromination and iodination of terminal alkynes

Direct halogenation, including chlorination, bromination and iodination of terminal alkynes, are of great importance in organic synthesis. Here an efficient and recyclable nano-Ag/g-C3N4 catalyst system was developed and proved to be remarkably active with 39 examples varied from chlorination, bromination to iodination, of which 14 runs have yielded more than 95% of the product. Recycling of the catalyst was also achieved without obvious activity loss after several runs: 99% yield was observed even after 5 runs in the bromination of phenylacetylene. The catalysts system is of low cost and easy to be prepared, making this procedure versatile, convenient and economic.

Csp-Csp3 Bond Formation via Iron(III)-Promoted Hydroalkynylation of Unactivated Alkenes

An iron(III)-promoted hydroalkynylation of unactivated alkenes toward Csp-Csp3 bond formation has been developed. Various alkenes, including mono-, di-, and trisubstituted alkenes, could all smoothly convert to structural diversified alkynes in this chemoselective protocol. Additionally, the scalability was unraveled and the further divergent transformations of products were conducted to demonstrate the synthetic utility.

Regioselective Synthesis of 5-Aminooxazoles via Cp?Co(III)-Catalyzed Formal [3 + 2] Cycloaddition of N-(Pivaloyloxy)amides with Ynamides

A simple and efficient protocol for the regioselective synthesis of 5-aminooxazoles is disclosed. The reaction, catalyzed by a cheap Cp?Co(III) catalyst, starts from easily accessible N-(pivaloyloxy)amides and ynamides. Mild reaction conditions, a broad s

Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles

In this contribution, the synthesis of long chain hexatriynyl- and octatetraynyl-substituted pyrroles in one step from 1-halopolyyne precursors is reported. The products were obtained via a mechanochemical approach by simple grinding of 1-haloalkynes with

Palladium end-capped polyynes via oxidative addition of 1-haloalkynes to Pd(PPh3)4

Reported here is the use of 1-haloacetylenes and 1-halopolyynes as synthons for the preparation of new palladium(II) end-capped polyynes. The 1-haloalkynes were obtained in a series of transformations from para-substituted bromoarenes that included Sonogashira coupling followed by halogenation and chain elongation via Cadiot-Chodkiewicz protocol. The key step for the synthesis of metal complexes was oxidative addition of 1-haloalkynes to Pd(PPh3)4, which allowed obtaining a series of metal compounds 1-5-CnX with carbon chains up to hexatriyne in 75-100% yield. All the compounds were characterized by NMR and HRMS or elemental analysis. The 13C spectra of the 1-haloalkynes showed interesting, although expected, shifts of the carbon chain atoms close to the halogen termini. X-ray crystal structures were obtained for three polyynes-two butadiynes (2-C4[Pd]Br and 3-C4[Pd]Br) and one hexatriyne (1-C6[Pd]Br)-and the latter is the first reported X-ray crystal structure of palladium end-capped hexatriyne.