131558-77-5

Upstream product

• 35843-78-8 1-bromo-5-decyne 
• 696-62-8 para-iodoanisole 
• 693-02-7 hex-1-yne 
• 1942-46-7 5-decyne 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 66107-29-7 4-methoxyphenyl triflate 
• 623-12-1 4-chloromethoxybenzene 
• 19013-30-0 p-methoxyphenyl mesylate 
• 5076-68-6 diethyl 4-methoxyphenyl phosphate 
• 67-56-1 methanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 42930-39-2 n-butylzinc chloride 
• 768-60-5 4-methoxyphenylacetylen 
• 35460-19-6 1-(methylthio)-1-hexyne 

Downstream Products

• 6397-82-6 4'-methoxyhexanophenone 
• 477202-13-4 1-(4-methoxyphenyl)-2-hexanone 

Relevant academic research and scientific papers

Highly Regio and Stereoselective Intermolecular Seleno- and Thioamination of Alkynes

By using N-fluorobenzenesulfonimide as both the oxidant and the amination reagent, we have realized the first example of the intermolecular chalcogenative amination of alkynes, which grants facile, highly regio- and stereoselective access to chalcogenated enamides. The reaction features mild conditions, high yields and selectivities, remarkably broad substrate scope, and excellent functional group tolerance. Mechanistic studies indicate the in situ generated chalcogen imidates to be the actual reactive species, which in turn, has clarified the mechanism of related transformations. These reactions represent significant additions to the development of the highly selective amino bisfunctionalization of alkynes.

Ni(O) catalyzed reactions of aryl and vinyl halides with alkenes and alkynes

NI[P(OPh)3]4 and Ni[P(OET)3]4 catalyze the reaction of aryl and vinyl halides with olefins (Heck reaction) and alkynes.

Water-soluble polymer-bound, recoverable palladium(0)-phosphine catalysts

The synthesis of a water-soluble polymer-bound Pd(0)-phosphine catalyst is described. This soluble polymeric catalyst is soluble in aqueous or mixed aqueous/organic media and has high activity in nucleophilic allylic substitution and in sp-sp2 coupling reactions of aryl iodides with terminal alkynes. The catalyst can be recycled efficiently by solvent or thermal precipitation methods.

A coordination driven self-assembled Pd6L8 nanoball catalyses copper and phosphine-free Sonogashira coupling reaction in both homogeneous and heterogeneous formats

A Pd6L8 type coordination driven self-assembly was constructed using a tripodal ligand L (L = N1,N3,N5-trimethyl-N1,N3,N5-tris[(pyridin-4-yl)methyl]-1,3,5-benzene tric

Carbamoyl-Substituted N-Heterocyclic Carbene Complexes of Palladium(II): Application to Sonogashira Cross-Coupling Reactions

(matrix presented) The first examples of N-carbamoyl-substituted heterocyclic carbene Pd(II) complexes are described. These thermal and hydrolytically stable complexes are readily prepared from carbamoyl imidazolium salts and efficiently promote Sonogashi

CuI-catalyzed Suzuki coupling reaction of organoboronic acids with alkynyl bromides

A CuI-catalyzed Suzuki cross-coupling reaction of organoboron derivatives with alkynyl bromides has been developed. In the presence of CuI (10 mol %) and 8-hydroxyquinoline (20 mol %), organoboron derivatives including aromatic and alkenyl boronic acids, potassium aryltrifluoroborates, and sodium tetraphenylborate reacted smoothly with 1-bromo-2-substituted acetylene to generate the corresponding cross-coupling products in good to excellent yields in C2H5OH. It is important to note that aromatic N,O-ligand 8-hydroxyquinoline is the most effective ligand for the reaction.

Enantioselective Ni/N-Heterocyclic Carbene-Catalyzed Redox-Economical Coupling of Aldehydes, Alkynes, and Enones for Rapid Construction of Acyclic All-Carbon Quaternary Stereocenters

Acyclic quaternary carbon stereocenters exist widely in natural products and bioactive molecules, but their enantioselective construction remains a prominent challenge. In particular, multicomponent enantioselective couplings of simple precursors to acyclic all-carbon quaternary stereocenters are very rare. We describe herein an N-heterocyclic carbene (NHC)-Ni catalyzed redox-economical three-component reaction of aldehydes, alkynes, and enones that proceeds in a highly chemo-, regio-, and enantioselective manner. A wide variety of valuable acyclic α-quaternary chiral ketones were synthesized in a single step with 100% atom economy. This reaction proceeds through the formation of a transient cyclic enolate followed by an aldol reaction/ring-opening sequence. The strategy is expected to inspire new and efficient approaches to generate other acyclic quaternary stereocenters.

Electrochemical Sulfonylation of Alkynes with Sulfonyl Hydrazides: A Metal- and Oxidant-Free Protocol for the Synthesis of Alkynyl Sulfones

Herein, an electrochemical oxidative cross-coupling reaction between terminal alkynes and sulfonylhydrazides has been developed. Tetrabutylammonium iodide is used as the electrolyte and redox medium. The significant advantages of this method are high atom efficiency, functional group tolerance, and transition metal- and oxidant-free conditions. Most of the compounds exhibit good inhibitory activity on tumor cell lines, and one of the compounds can inhibit cell migration and induce apoptosis in HeLa cells. (Figure presented.).

Cu2O Nanocrystals-Catalyzed Photoredox Sonogashira Coupling of Terminal Alkynes and Arylhalides Enhanced by CO2

Herein the first visible-light-activated Sonogashira C?C coupling reaction at room temperature catalyzed by single-metal heterogeneous Cu2O truncated nanocubes (Cu2O TNCs) was developed. A wide variety of aryl halides and terminal alkynes worked well in this recyclable heterogeneous photochemical process to form the corresponding Sonogashira C?C coupling products in good yields. Mechanistic control studies indicated that CO2 enhances the formation of light-absorbing heterogeneous surface-bound CuI-phenylacetylide (λmax=472 nm), which further undergoes single-electron transfer with aryl iodides/bromides to enable Sonogashira Csp2 ?Csp bond formation. In contrast to literature-reported bimetallic TiO2-containing nanoparticles as photocatalyst, this work avoided the need of cocatalysis by TiO2. Single-metal CuI in Cu2O TNCs was solely responsible for the observed Csp2 ?Csp coupling reactions under CO2 atmosphere.

Sodium-metal-promoted reductive 1,2-syn-diboration of alkynes with reduction-resistant trimethoxyborane

Reductive 1,2-diboration of alkynes has been accomplished by means of sodium dispersion in the presence of trimethoxyborane as a reduction-resistant boron electrophile. Two boron moieties can be introduced onto alkynes with excellent syn selectivity to afford the corresponding (Z)-1,2-diborylalkenes. Bis(borate) species generated in situ can be involved in one-pot Suzuki-Miyaura arylation, formal arylboration of alkynes thus being executed.