119754-17-5

Upstream product

• 220659-84-7 4-(2-(trimethylsilyl)ethynyl)benzophenone 
• 90-90-4 (4-bromophenyl)(phenyl)methanone 
• 6136-66-9 4-iodobenzophenone 
• 1066-54-2 trimethylsilylacetylene 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 1137-41-3 (4-aminophenyl)(phenyl)methanone 
• 119754-14-2 4-(4-benzoylphenyl)-2-methyl-3-butyn-2-ol 

Downstream Products

• 1271731-35-1 4-(2-triphenylenylethynyl)benzophenone 
• 1388753-75-0 phenyl(4-{2-[(trifluoromethyl)sulfanyl]ethynyl}phenyl)methanone 
• 3139-85-3 4-vinylbenzophenone 

Relevant academic research and scientific papers

Iron-Catalyzed Vinylzincation of Terminal Alkynes

Organozinc reagents are among the most commonly used organometallic reagents in modern synthetic chemistry, and multifunctionalized organozinc reagents can be synthesized from structurally simple, readily available ones by means of alkyne carbozincation. However, this method suffers from poor tolerance for terminal alkynes, and transformation of the newly introduced organic groups is difficult, which limits its applications. Herein, we report a method for vinylzincation of terminal alkynes catalyzed by newly developed iron catalysts bearing 1,10-phenanthroline-imine ligands. This method provides efficient access to novel organozinc reagents with a diverse array of structures and functional groups from readily available vinylzinc reagents and terminal alkynes. The method features excellent functional group tolerance (tolerated functional groups include amino, amide, cyano, ester, hydroxyl, sulfonyl, acetal, phosphono, pyridyl), a good substrate scope (suitable terminal alkynes include aryl, alkenyl, and alkyl acetylenes bearing various functional groups), and high chemoselectivity, regioselectivity, and stereoselectivity. The method could significantly improve the synthetic efficiency of various important bioactive molecules, including vitamin A. Mechanistic studies indicate that the new iron-1,10-phenanthroline-imine catalysts developed in this study have an extremely crowded reaction pocket, which promotes efficient transfer of the vinyl group to the alkynes, disfavors substitution reactions between the zinc reagent and the terminal C–H bond of the alkynes, and prevents the further reactions of the products. Our findings show that iron catalysts can be superior to other metal catalysts in terms of activity, chemoselectivity, regioselectivity, and stereoselectivity when suitable ligands are used.

Multi-fold Sonogashira coupling: A new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties

For the first time, a direct single-step one-pot route to access nine new symmetric tetraalkynylated anthracenes via Pd(CH3CN)2Cl2/cataCXiumA catalyzed tetra-fold Sonogashira coupling is reported. Five of these tetraalkynylated anthracenes have been crystallographically characterized, with two of them exhibiting multiple interactions that significantly shorten the inter-planar distances in the solid-state structure. The rich photophysical properties exhibited by these molecules hold immense promise for future applications in sensors and optoelectronic devices. Two of the considered tetraalkynylated anthracenes comprising a D-π-A-π-D motif demonstrate solvatochromism and halochromism, with one of them showing a low bandgap of 1.79 eV. The remaining compounds demonstrate bandgaps in the range of 1.79-2.04 eV.

Photo-induced phosphorus radical involved semipinacol rearrangement reaction: Highly synthesis of γ-oxo-phosphonates

Hydroxyphosphoric acids display the unique biological activities, and they have some attractive prospects as clinical drug moleculars. Herein, a new approach for the synthesis of γ-oxo-phosphonates (the precursor of hydroxyphosphoric acid) has been established through the semipinacol rearrangement tactic involved the photo-induced phosphorus radical process. Most important, this transformation is avoid of the external oxidants, and occurs very well under the sunlight irradiation, meanwhile the γ-oxo-phosphonate was easily derivatized to obtain γ-hydroxyphosphoric acid, thus highlights the synthesis value of this method.

Diboron-Assisted Copper-Catalyzed Z-Selective Semihydrogenation of Alkynes Using Ethanol as a Hydrogen Donor

We herein describe a B2Pin2-assisted copper-catalyzed semihydrogenation of alkynes. A variety of alkenes were obtained in good to excellent yields with Z-selectivity under mild reaction conditions. Mechanistic studies indicated that a transfer hydrogenation process was involved and ethanol acted as both a solvent and a hydrogen donor in this reaction. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes such as Z-Combretastain A4-d2 in a high deuteration ratio by using readily available ethanol-d1 as the deuterium source.

Aryl Nitriles from Alkynes Using tert -Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage

Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated. (Figure Presented).

Aerobic oxynitration of alkynes with tBuONO and TEMPO

An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.

Practical methods for the synthesis of trifluoromethylated alkynes: Oxidative trifluoromethylation of copper acetylides and alkynes

Two practical and complementary methods are reported for the synthesis of trifluoromethylated alkynes. The first one, a mix-and-stir process, is based on the oxidative trifluoromethylation of readily available and bench-stable copper acetylides while the second one, which displays a broad substrate scope and has several advantages over existing procedures, is based on the oxidative copper-catalyzed direct trifluoromethylation of terminal alkynes. Both reactions provide user-friendly processes for the synthesis of trifluoromethylated acetylenes which can be easily obtained from readily available starting materials.

Metal-free oxidative trifluoromethylthiolation of terminal alkynes with CF3SiMe3 and elemental sulfur

A metal-free oxidative trifluoromethyl-thiolation of terminal alkynes using readily available CF3SiMe3 and elemental sulfur at room temperature has been developed. This reaction provides an efficient and convenient method for the preparation of alkynyl trifluoromethyl sulfides bearing a wide range of functional groups. Preliminary investigation revealed that elemental sulfur instead of air acted as the oxidant.

Mori-Hiyama versus hay coupling for higher polyynes

Dimerizations of C4 precursors RCa=CCa=CTMS [R = C 6H5 (1), p-CH3C6H5, (2), 4-n-C5H11C6H4 (3), C 6H9 (4), p-CH3O

SUBSTITUTED ETHYNYL GOLD-NITROGENATED HETEROCYCLIC CARBENE COMPLEX AND ORGANIC ELECTROLUMINESCENT DEVICE USING SAME

The present invention provides a substituted ethynyl gold-nitrogen containing heterocyclic carbene complex represented by the general formula (1): wherein L represents a nitrogen containing heterocyclic carbene ligand; and X represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or a heterocyclic group; in which one or more hydrogen atoms on the carbon atom(s) of X may be replaced by a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, a dialkylamino group, an acyl group or an arylcarbonyl group; and, when more than one hydrogen atom on the carbon atom(s) of X is replaced by the alkyl group, the alkenyl group, the aryl group, the aralkyl group, the alkoxy group, the aryloxy group, the dialkylamino group, the acyl group or the arylcarbonyl group, the adjacent groups may be bonded together to form a ring, a method for preparing the same, and an organic electroluminescent device comprising the substituted ethynyl gold-nitrogen containing heterocyclic carbene complex in at least one organic compound thin layer.