33675-41-1

Upstream product

• 60-29-7 diethyl ether 
• 75-16-1 methylmagnesium bromide 
• 768-60-5 4-methoxyphenylacetylen 
• 60512-57-4 1-(2,2-dibromovinyl)-4-methoxybenzene 
• 2227-57-8 3-(4-methoxyphenyl)propynoic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 603-33-8 triphenylbismuthane 
• 696-62-8 para-iodoanisole 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 

Downstream Products

• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 22779-05-1 1,4-bis(4-methoxyphenyl)-1,3-butadiyne 
• 61926-37-2 1-(iodoethynyl)-4-methoxybenzene 
• 71609-39-7 4-Methoxytolazoline 
• 108030-81-5 2-(4-methoxyphenyl)pyrazine 
• 876564-85-1 1-methoxy-4-(Z-3-trimethylsilyl-4-trimethylsilylethynylhepta-3,6-dien-1-ynyl)benzene 
• 871731-54-3 (Z)-8-(4-methoxyphenyl)-5,6-diphenyloct-5-en-7-yn-4-ol 
• 934001-86-2 CH₃OCC₅H₄C₆H₁₁O₂C₃NOBr 
• 1043906-54-2 C₁₃H₁₀O₂ 
• 928154-75-0 N-allyl-N-((4-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide 
• 1120326-11-5 3-[(4-methoxyphenyl)ethynyl]-1H-indole 
• 1120326-15-9 C₁₈H₁₅NO 
• 1096704-12-9 dimethyl 2-allyl-2-(5-(4-methoxyphenyl)penta-2,4-diynyl)malonate 
• 1160723-48-7 N-benzyl-N-((4-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Formal total synthesis of selaginpulvilin D

An efficient and mild synthetic strategy for the total synthesis of selaginpulvilin D has been reported. A highly chemoselective enyne-alkyne dehydro Diels-Alder reaction has been employed for the construction of the tricyclic fluorene framework present i

Nickel-Catalyzed Difunctionalization of Alkynyl Bromides with Thiosulfonates and N -Arylthio Succinimides: A Convenient Synthesis of 1,2-Thiosulfonylethenes and 1,1-Dithioethenes

An efficient nickel-catalyzed vicinal thiosulfonylation of 1-bromoalkynes with thiosulfonates in the presence of cesium carbonate is described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provides a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields. The extensive substrate scope of both alkynyl bromides and thiosulfonates is explored with a broad range of functional groups. Indole-derived 1,1-bromoalkenes were also successfully explored in this 1,2-thiosulfonylation process. Moreover, the nickel-catalyzed geminal -dithiolation of alkynyl bromides with N -arylthio succinimides provides 1,1-dithioalkenes in high yields. The present protocol is reliable on gram scale, and a sequential one-pot bromination and thiosulfonylation of phenylacetylene is achieved in a scale-up synthesis. Following control experiments, a plausible mechanism is proposed to rationalize the experimental outcome and the vicinal thio-sulfonylation.

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.

Catalytic Cyclotrimerization Pathway for Synthesis of Selaginpulvilins C and D: Scope and Limitations

A facile and unified approach to the main selaginpulvilin's framework was achieved by catalytic [2 + 2 + 2]-cyclotrimerization of a triyne with monosubtituted alkynes. The reaction proceeded with high "ortho"selectivity by using Wilkinson's catalyst (RhCl

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.

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.).

A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization

Straightforward access to [1,2]-annulated indoles, key substructures in natural products, is highly desirable yet challenging. Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides is presented, providing a rapid access into [1,2]-annulated indoles by an intermolecular radical addition, intramolecular cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C-N bond formation, followed by an unusual aza-Nazarov cyclization.

Copper-catalyzed domino synthesis of ynamines

The hitherto unexploredN-alkynylation of electron-withdrawing or protecting group free N-heteroarenes such as indole, carbazole and pyrrole was developed usinggem-dibromoalkenes to synthesize ynamines under ligand-free copper-catalyzed domino conditions. The development methodology of ynamines was also applied in the synthesis of enynamines, multi-coupled bis-ynamines, tris-ynamines, and the natural product peyonine, demonstrating its broad synthetic scope and applications.