92985-68-7

Upstream product

• 766-97-2 4-n-methylphenylacetylene 
• 16954-96-4 diacetylene-d2 
• 108-88-3 toluene 
• 3240-11-7 Phenylacetylene-d1 
• 122-00-9 para-methylacetophenone 

Downstream Products

• 14939-05-0 1-phenyl-3-(4-methylphenyl)prop-2-yn-1-one 
• 1420041-75-3 1-chloro-4-((Z)-4-fluoro-4-p-tolylbut-3-en-1-ynyl)benzene 
• 1420041-67-3 ((Z)-4-fluoro-4-p-tolylbut-3-en-1-ynyl)trimethylsilane 
• 1420041-07-1 1-((Z)-2-bromo-1-fluorovinyl)-2-methylbenzene 
• 89039-26-9 C₁₅H₁₃⁽²⁾HClNO₂S 
• 89039-28-1 C₁₆H₁₆⁽²⁾HClS 

Relevant academic research and scientific papers

Mechanistic Insights into the B(C6F5)3-Initiated Aldehyde-Aniline-Alkyne Reaction to Form Substituted Quinolines

A substoichiometric quantity of the Lewis acid B(C6F5)3 is sufficient to initiate the aldehyde-amine-alkyne reaction, in a one-pot methodology that enables the synthesis of a range of functionalized quinolines. Optimization studies revealed that key requirements for the high-yielding tricomponent reaction initiated by B(C6F5)3 at raised temperatures include an excess of the in situ generated imine (which acts as a hydrogen acceptor) and an alkyne substituent able to stabilize positive charge buildup during the cyclization. Mechanistic experiments revealed that under these conditions B(C6F5)3 is acting as a Lewis acid-assisted Br?nsted acid, with H2O-B(C6F5)3 being the key species enabling catalytic quinoline formation. This was indicated by deuterium labeling studies and the observation that the cyclization of N-(3-phenylpropargyl)aniline using B(C6F5)3 under anhydrous conditions afforded the zwitterion [(N-H-3-B(C6F5)3-4-Ph-quinolinium], which does not undergo protodeboronation to release B(C6F5)3 and the quinoline product under a range of conditions. Finally, a brief substrate scope exploration demonstrated that this is an operationally simple and effective methodology for the production of functionalized quinolines.

Base-Promoted Nitrile-Alkyne Domino-Type Cyclization: A General Method to Trisubstituted Imidazoles

An efficient base promoted nitrile-alkyne domino-type cyclization for multicomponent assembly of imidazoles from alkynes, nitriles, and tBuOK has been developed, which could run even in the absence of solvent on a gram scale with complete atom economy. This method contributes directly to reaching the synthesis of valuable imidazole derivatives from readily available raw materials.

Creating Dynamic Nanospaces in Solution by Cationic Cages as Multirole Catalytic Platform for Unconventional C(sp)?H Activation Beyond Enzyme Mimics

Herein we demonstrate that, based on the creation of dynamic nanospaces in solution by highly charged positive coordination cage of [Pd6(RuL3)8]28+, multirole and multi-way cage-confined catalysis is accomplisha

A practical and efficient method for late-stage deuteration of terminal alkynes with silver salt as catalyst

A practical and efficient H/D exchange method for selective deuteration of terminal alkynes was disclosed. The reaction was simply performed with CF3COOAg as catalyst at room temperature, affording products with high level of deuterium incorporation. The excellent site-selectivity and promising functional group tolerance of this protocol enabled deuteration of pharmaceuticals and nature product derivatives.

Iron-Catalyzed Tertiary Alkylation of Terminal Alkynes with 1,3-Diesters via a Functionalized Alkyl Radical

Direct oxidative C(sp)?H/C(sp3)?H cross-coupling offers an ideal and environmentally benign protocol for C(sp)?C(sp3) bond formations. As such, reactivity and site-selectivity with respect to C(sp3)?H bond cleavage have remained a persistent challenge. Herein is reported a simple method for iron-catalyzed/silver-mediated tertiary alkylation of terminal alkynes with readily available and versatile 1,3-dicarbonyl compounds. The reaction is suitable for an array of substrates and proceeds in a highly selective manner even employing alkanes containing other tertiary, benzylic, and C(sp3)?H bonds alpha to heteroatoms. Elaboration of the products enables the synthesis of a series of versatile building blocks. Control experiments implicate the in situ generation of a tertiary carbon-centered radical species.

Partial Reduction and Selective Transfer of Hydrogen Chloride on Catalytic Gold Nanoparticles

HCl in solution accepts electron density from Au NPs and partially reduces at room temperature, as occurs with other simple diatomic molecules, such as O2 and H2. The activation can be run catalytically in the presence of alkynes to give exclusively E-vinyl chlorides, after the regio- and stereoselective transfer of HCl. Based also on this method, vinyl chloride monomer (VCM) can be produced in a milder and greener way than current industrial processes.

Organocatalytic Imidazolium Ionic Liquids H/D Exchange Catalysts

Simple 1,2,3-trialkylimidazolium cation associated with basic anions, such as hydrogen carbonate, prolinate, and imidazolate, is an active catalyst for the H/D exchange reaction of various substrates using CDCl3 as D source, without the addition of any extra bases or metal. High deuterium incorporation (up to 49%) in acidic C-H bonds of ketone and alkyne substrates (pKa from 18.7 to 28.8) was found at room temperature. The reaction proceeds through the fast and reversible deuteration of the 2-methyl H of the imidazolium cation followed by D transfer to the substrate. The IL acts as a neutral base catalyst in which the contact ion pair is maintained in the course of the reaction. The basic active site is due to the presence of a remote basic site in the anion namely, OH of bicarbonate, NH of prolinate, and activated water in the imidazolate anion. Detailed kinetic experiments demonstrate that the reaction is first order on the substrate and pseudozero order relative to the ionic liquid, due to the fast reversible reaction involving the deuteration of the ionic liquid by the solvent.

Reaction of alkynes and azides: Not triazoles through copper-acetylides but oxazoles through copper-nitrene intermediates

Well-defined copper(I) complexes of composition [Tpm* ,BrCu(NCMe)]BF4 (Tpm*,Br=tris(3,5- dimethyl-4-bromo-pyrazolyl)methane) or [Tpa* Cu]PF6 (Tpa=tris(3,5-dimethyl-pyrazolylmethyl)amine) catalyze the formation of 2,5-disubstituted oxazoles from carbonyl azides and terminal alkynes in a direct manner. This process represents a novel procedure for the synthesis of this valuable heterocycle from readily available starting materials, leading exclusively to the 2,5-isomer, attesting to a completely regioselective transformation. Experimental evidence and computational studies have allowed the proposal of a reaction mechanism based on the initial formation of a copper-acyl nitrene species, in contrast to the well-known mechanism for the copper-catalyzed alkyne and azide cycloaddition reactions (CuAAC) that is triggered by the formation of a copper-acetylide complex.

Ultraviolet photochemistry of diacetylene: Reactions with benzene and toluene

The reactions of metastable diacetylene with benzene and toluene are explored using a molecular beam pump-probe time-of-flight mass spectrometer. Diacetylene is laser-excited to the 210610 band of the 1Δu←X1Σ+g transition, whereupon rapid intersystem crossing occurs to the lowest triplet states. The triplet state diacetylene then reacts with either benzene or toluene as the gas mixture traverses a short reaction tube (approximately 20 μs). The reactions are quenched as the gas mixture expands into the ion source region of a time-of-flight mass spectrometer where the primary photoproducts are detected using vacuum ultraviolet (VUV) photoionization or resonant two-photon ionization (R2PI). The major products from the reaction of diacetylene and benzene have molecular formulas C8H6 and C10H6, and are identified as phenylacetylene and phenyldiacetylene using R2PI spectroscopy. The major products from metastable diacetylene's reaction with toluene are C9H8 and C11H8. The C9H8 product is confirmed as a mixture of o-, m-, and p-ethynyltoluene, with the ortho product dominating. Mechanisms for the formation of the above products are proposed based on deuterium substitution studies of the reactions. The potential importance of these reactions is discussed as they relate to hydrocarbon growth in sooting flames.

Stereomutation in the Seyferth Reaction

The cyclopropanation reaction between dibromomethylene (:CBr2) from the Seyferth reagent (PhHgCBr3) and electron-deficient alkenes is nonstereospecific.Thus fumaronitrile, styrene-cis-β-d, and trans-1,2-dichloroethene give mixtures of the respective cis a