4440-01-1

Usage

Uses

Used in Organic Synthesis:
Lithium Phenylacetylide is used as a reagent in organic reactions for the addition of the ethynylbenzene group to a compound. This allows for the formation of new chemical bonds and the synthesis of a wide range of organic compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Lithium Phenylacetylide is used as a key intermediate in the synthesis of various drug molecules. Its ability to form new chemical bonds and create complex structures makes it a valuable tool in the development of new medications.
Used in Material Science:
In the field of material science, Lithium Phenylacetylide is utilized in the synthesis of advanced materials with unique properties. Its use in creating novel compounds can lead to the development of new materials with improved performance in various applications, such as electronics, energy storage, and coatings.
Used in Chemical Research:
Lithium Phenylacetylide is also used in chemical research as a model compound to study the reactivity and properties of organometallic compounds. Understanding its behavior can provide insights into the development of new synthetic methods and the design of more efficient catalysts.

InChI:InChI=1/C8H5.Li/c1-2-8-6-4-3-5-7-8;/h3-7H;/rC8H5Li/c9-7-6-8-4-2-1-3-5-8/h1-5H

Upstream product

• 591-51-5 phenyllithium 
• 536-74-3 phenylacetylene 
• 109-72-8 n-butyllithium 
• 103-64-0 bromostyrene 
• 75-78-5 dimethylsilicon dichloride 
• 5321-47-1 1-(2-methylbenzyl)piperazine 
• 63839-20-3 4-methoxyphenylcarbonimidic dichloride 
• 59610-41-2 lithium bis(trimethylsilyl)phosphanide-tetrahydrofuran (1/2) 

Downstream Products

• 1006-67-3 5-phenylisoxazole 
• 5394-80-9 (E)-1,5-diphenyl-3-(phenylethynyl)pent-1-en-4-yn-3-ol 
• 82031-71-8 trans-2-(2-phenylethynyl)-1-cyclohexanol 
• 24243-06-9 3-methyl-1,5-diphenylpenta-1,4-diyn-3-ol 
• 17213-89-7 10-hydroxy-10-(phenylethynyl)anthracen-9(10H)-one 
• 1483-82-5 phenylethynyl chloride 
• 18866-47-2 tris(phenylethynyl)phenylsilane 
• 116153-39-0 9,10-bis(phenylethynyl)phenanthrene-9,10-diol 
• 18784-61-7 1,1-diphenylbis(phenylethynyl)silane 
• 50428-40-5 Tris(phenylethynyl)methyl alcohol 
• 55006-58-1 1,4-bis(phenylethynyl)-2,5-cyclohexadiene-1,4-diol 
• 2579-22-8 Phenylpropargyl aldehyde 
• 62698-35-5 1-phenyl-1-p-methoxyphenyl-3-phenylpropargyl alcohol 
• 548796-81-2 1,1-di(p-methoxyphenyl)-3-phenylpropargyl alcohol 

Relevant academic research and scientific papers

Mechanistic Study of Pd/NHC-Catalyzed Sonogashira Reaction: Discovery of NHC-Ethynyl Coupling Process

The product of a revealed transformation—NHC-ethynyl coupling—was observed as a catalyst transformation pathway in the Sonogashira cross-coupling, catalyzed by Pd/NHC complexes. The 2-ethynylated azolium salt was isolated in individual form and fully char

Carbon monoxide-isocyanide coupling promoted by acetylide addition to a diiron complex

C-N bond formation involving carbon monoxide and isocyanide ligands is promoted by addition of a series of lithium acetylides to a diiron μ-aminocarbyne complex, i.e. [Fe2{μ-CN(Me)(Xyl)}(μ-CO)(CO)(CNXyl)(Cp)2][SO3CF3

A Germylene/Borane Lewis Pair and the Remarkable C=O Bond Cleavage Reaction toward Isocyanate and Ketone Molecules

A germylene/borane Lewis pair (2) was prepared from a 1,1-carboboration of amidinato phenylethynylgermylene (1) by B(C6F5)3. Compound 2 reacted with iPrNCO and (4-MeOC6H4)C(O)Me, respectively, with cleavage of the C=O double bond. In the first instance, O and iPrNC insert separately into the Ge?B bond to yield a GeBC2O-heterocycle (3) and a GeBC3-heterocycle (4). In the second case (4-MeOC6H4)(Me)C inserts into the Ge?N bond of 2 while O is incorporated in the Ge?B bond to form a Ge-centered spiroheterocycle (5). The reaction of 2 with tBuNC to give 6, which has almost the same structure as 4, proved the formation of the isonitrile during transformation from 2 and iPrNCO to 3 and 4. The kinetic study of the reaction of 2 and iPrNCO gave evidence of proceeding through a GeBC3O-heterocycle intermediate. In addition, a DFT study was performed to elucidate the reaction mechanism.

Cu(II)-Cu(I) synergistic cooperation to lead the alkyne C-H activation

An efficient alkyne C-H activation and homocoupling procedure has been studied which indicates that a Cu(II)/Cu(I) synergistic cooperation might be involved. In situ Raman spectroscopy was employed to study kinetic behavior, drawing the conclusion that Cu(I) rather than Cu(II) participates in the rate-determining step. IR, EPR, and X-ray absorption spectroscopy evidence were provided for structural information, indicating that Cu(I) has a stronger interaction with alkyne than Cu(II) in the C-H activation step. Kinetics study showed Cu(II) plays a role as oxidant in C-C bond construction step, which was a fast step in the reaction. X-band EPR spectroscopy showed that the coordination environment of CuCl2(TMEDA) was affected by Cu(I). A putative mechanism with Cu(I)-Cu(II) synergistic cooperation procedure is proposed for the reaction.

Dibridgehead diphosphines that turn themselves inside out

Molecular contortionists can lurk in unexpected places. The title compounds undergo equilibria that appear to involve straightforward pyramidal inversions at the phosphorus atoms, but in reality the stereoisomers interconvert by turning themselves inside

Pd-catalyzed sp-sp3cross-coupling of benzyl bromides using lithium acetylides

Organolithium-based cross-coupling reactions have emerged as an indispensable method to construct C-C bonds. These transformations have proven particularly useful for the direct and fast coupling of various organolithium reagents (sp, sp2, and sp3) with aromatic (pseudo) halides (sp2). Here we present an efficient method for the cross-coupling of benzyl bromides (sp3) with lithium acetylides (sp). The reaction proceeds within 10 min at room temperature and can be performed in the presence of organolithium-sensitive functional groups such as esters, nitriles, amides and boronic esters. The potential application of the methodology is demonstrated in the preparation of key intermediates used in pharmaceuticals, chemical biology and natural products.

Synthesis, antitumor activity, and cytotoxicity of 4-substituted 1-benzyl-5-diphenylstibano-1H-1,2,3-triazoles

Trisubstituted 5-organostibano-1H-1,2,3-triazoles (3a–f) were synthesized by the Cu-catalyzed azide-alkyne cycloaddition of various ethynylstibanes (1) with benzylazide (2) in the presence of CuBr (5 mol%) under aerobic conditions. The reaction of 5-stiba

The Synthesis of Alkyl and (Hetero)aryl Sulfonamides from Sulfamoyl Inner Salts

An approach to the synthesis of sulfonamides from sulfamoyl inner salts and organometallic species is presented. A range of sulfamoyl carbamates, amines, and metals are explored. Primary, secondary, and tertiary alkyl-, aryl-, and heteroaryllitihium and magnesium nucleophiles were successful. This approach yields bench-stable intermediates and avoids many of the functional group incompatibilities, regioselectivity issues, and high-energy reagents generally associated with the synthesis of sulfonamides. Additionally, the products may be purified by basic extraction or salt formation, avoiding chromatography.

Reactions of phenylacetylene with nickel POCOP-pincer hydride complexes resulting in different outcomes from their palladium analogues

Nickel POCOP-pincer hydride complexes [2,6-(R2PO)2C6H3]NiH (R = iPr, 4a; R = cPe = cyclopentyl, 4b) react with phenylacetylene to generate [2,6-(R2PO)2C6H3]NiC(Ph)=CH2 (5a-b) as the major product and (E)-[2,6-(R2PO)2C6H3]NiCH=CHPh (6a-b) as the minor product. The 2,1-insertion is more favorable than the 1,2-insertion and both pathways involve cis addition of Ni-H across the C≡C bond. Unlike the palladium case, alkynyl complexes [2,6-(R2PO)2C6H3]NiC≡CPh (7a-b) and H2 are not produced in the nickel system. The more bulky hydride complex [2,6-(tBu2PO)2C6H3]NiH (4c) shows no reactivity towards phenylacetylene. Catalytic hydrogenation of phenylacetylene with 4a-b takes place at an elevated temperature (70-100 °C) and proves to be heterogeneous. The structures of 5b, 6a, 7a and 7b have been studied by X-ray crystallography.

BF3-mediated oxidative cross-coupling of pyridines with alkynyllithium reagents and further reductive functionalizations of the pyridine scaffold

A set of functionalized alkynylpyridines can be readily obtained using Et2O·BF3 as promoter. Alkynyllithium reagents undergo an addition reaction at position C-2 of pyridines that are rearomatized by oxidative treatment with chloranil. These substituted pyridines can be easily converted into more valuable intermediates. Examples of applications are given as well. Finally, the synthesis of piperidines and lactams via first an oxidative BF3-mediated addition reaction followed by a NaBH 4 reduction or acidic workup is also described. Georg Thieme Verlag Stuttgart New York.