33491-03-1

Upstream product

• 3201-63-6 -triphenyl-phosphoran 
• 77295-59-1 1-chloro-4-(2,2-dibromovinyl)benzene 
• 3240-10-6 (4-chlorophenyl)propiolic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 1777-56-6 4-chlorobenzoylmethylenetriphenylphosphorane 
• 622-95-7 4-chlorobenzyl bromide 
• 81559-60-6 1-Chloro-4-(2,2,2-tribromo-ethyl)-benzene 
• 50650-48-1 1-ethynyl-4-chloro-benzene; mercury (II)-compound 
• 873-73-4 4-n-chlorophenylacetylene 
• 78704-49-1 1-(4-chlorophenyl)-2-trimethylsilylacetylene 

Downstream Products

• 23464-21-3 5-(p-Chlorphenyl)-penta-2,4-diinal-diethylacetal 
• 39654-03-0 (p-Chlorphenyl)-aethinyl-p-methylphenyl-sulfid 
• 23463-82-3 5--pentadiin-(2.4)-saeure 
• 873-73-4 4-n-chlorophenylacetylene 
• 33491-02-0 1-chloro-4-(chloroethynyl)benzene 
• 39654-08-5 Di-(p-tolylthio)-(p-chlorphenyl)-ethen 
• 934001-84-0 ClC₆H₄C₆H₁₁O₂C₃NOBr 
• 854015-60-4 [4-bromo-5-(4-chlorophenyl)-isoxazole-3-yl]-methyl alcohol 
• 1160723-52-3 N-benzyl-N-((4-chlorophenyl)ethynyl)-4-methylbenzenesulfonamide 
• 1160723-53-4 N-(2-(4-chlorophenyl)ethynyl)-N-methanesulfonylbenzylamine 
• 1160723-51-2 (S)-3-(2-(4-chlorophenyl)ethynyl)-4-phenyloxazolidin-2-one 
• 1160723-50-1 (S)-3-(2-(4-chlorophenyl)ethynyl)-4-methyloxazolidin-2-one 
• 1187772-36-6 2-[(4-chlorophenyl)ethynyl]benzoxazole 
• 1225649-66-0 9-chloro-6-((4-chlorophenyl)ethynyl)-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole 

Relevant academic research and scientific papers

Regio- and Stereoselective N-addition to an Open Bromo Vinyl Cation

A protocol for the synthesis of thus far inaccessible bromo vinyl triflimides is presented. Our previously reported concept of assisted vinyl cation formation was engaged to achieve both a protonation of relatively electron poor bromo alkynes and a reaction with high regio- and stereoselectivity. To the best of our knowledge, this is the first stereoselective addition of an N-nucleophile to an open β-halovinyl cation.

Visible-Light-Promoted Formation of C—C and C—P Bonds Derived from Evolution of Bromoalkynes under Additive-Free Conditions: Synthesis of 1,1-Dibromo-1-en-3-ynes and Alkynylphosphine Oxides

The controllable achievement of C—C and C—P bond formations is developed via visible-light-promoted bromoalkyne dimerization or its further transformation with secondary phosphine oxides. The 1,1-dibromo-1-en-3-ynes are formed when bromoalkyne is exposed to visible-light. While alkynylphosphine oxides are generated when bromoalkynes are mixed with secondary phosphine oxides.

Copper-Catalyzed Perfluoroalkylation of Alkynyl Bromides and Terminal Alkynes

A copper-catalyzed one-pot perfluoroalkylation of alkynyl bromides and terminal alkynes has been disclosed, and the corresponding perfluoroalkylated alkynes could be attained in good to excellent yields. The new straightforward transformation shows high efficiency (0.01-0.5 mol % catalyst loading), broad substrate scope, and remarkable functional group tolerance and provides a facile approach for useful application in life and material sciences.

Fully Substituted Conjugate Benzofuran Core: Multiyne Cascade Coupling and Oxidation of Cyclopropenone

An unprecedented C═C double bond cleavage of cyclopropenone and dioxygen activation by multiyne cascade coupling has been developed. This chemistry provides a novel, simple, and efficient approach to synthesize fully substituted conjugate benzofuran derivatives from simple substrates under mild conditions. The density functional theory (DFT) calculations reveal that the unique homolytic cleavages of cyclopropenone and molecular oxygen are crucial to the success of this reaction.

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.).

A Unified Approach for Divergent Synthesis of Heterocycles via TMSOTf-Catalyzed Formal [3+2] Cycloaddition of Electron-Rich Alkynes

We present a synthetic protocol for the construction of polysubstituted five-membered heterocycles via TMSOTf-catalyzed formal [3+2] cycloaddition of electron-rich alkynes, which features free from any metal, atom economy and water as the main by-product. Furthermore, alkenyl ether adduct has been verified as the key intermediate. Notably, by utilizing this approach, we can synthesize a broad range of polysubstituted furans, thiophenes and pyrroles, and extend this transformation to deliver fused-polyheterocycles. This reaction can be achieved on a gram scale and the corresponding products are intermediates for producing diverse potentially useful scaffolds. (Figure presented.).

Epoxyanthracene Derivatives and Dicarbonylation on Benzene Ring via Hexadehydro-Diels-Alder (HDDA) Derived Benzynes with Oxazoles

A capture reaction of hexadehydro-Diels-Alder (HDDA) derived benzyne with various substituted oxazoles is reported. With methyl, hydrogen, or phenyl as the substituent at 2-position of oxazole, tetraynes afforded epoxyanthracene derivatives or underwent dicarbonylation on benzene ring. The reaction does not require any catalyst or additive. The mechanism behind the reaction was investigated. The obtained polycyclic product structure has potential application value in optoelectronic materials. The availability of dicarbonylated arene implies the uniqueness of HDDA benzyne reaction compared with traditional benzyne.

Direct oxidation ofN-ynylsulfonamides intoN-sulfonyloxoacetamides with DMSO as a nucleophilic oxidant

N-Arylethynylsulfonamides are oxidized intoN-sulfonyl-2-aryloxoacetamides directly and efficiently with dimethyl sulfoxide (DMSO) as both an oxidant and solvent with microwave assistance. DFT calculations indicate that DMSO nucleophilically attacks the ethylic triple bond and transfers its oxygen atom to the triple bond to form zwitterionic anionicN-sulfonyliminiums to trigger the reaction. Then it nucleophilically attacks the generated iminium intermediates to accomplish the oxidationviathe second oxygen atom transfer. The current method provides a straightforward and efficient strategy to transform variousN-arylethynylsulfonamides intoN-sulfonyl-2-aryloxoacetamides, sulfonyl oxoacetimides, without any other electrophilic activators or oxidants.

Access to Benzoxazepines and Fully Substituted Indoles via HDDA Coupling

The HDDA-derived benzyne intermediate was captured by oxazolines based on the addition reaction of benzyne to the Ca?N double bond. Benzoxazepine derivatives, fused benzoxazepine derivatives, and fully substituted indoles are synthesized in one step. The reaction does not require any catalyst or additives. Possible reaction mechanisms are presented.