313343-88-3

Upstream product

• 705-31-7 4-trifluoromethylphenylacetylene 
• 455-13-0 4-Iodobenzotrifluoride 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 131356-53-1 1-(2,2-dibromovinyl)-4-(trifluoromethyl)benzeney 

Downstream Products

• 928154-76-1 N-2-propenyl-N-[p-(trifluoromethyl)phenylethynyl]-p-toluenesulfonamide 
• 1187772-37-7 2-[(4-trifluoromethylphenyl)ethynyl]benzoxazole 
• 1197210-73-3 1-(4-trifluoromethyl-phenylethynyl)-1H-imidazole 
• 1206482-97-4 5-phenyl-2-(4-trifluoromethyl-phenylethynyl)-oxazole 
• 1207551-85-6 2-phenyl-5-[(4-trifluoromethylphenyl)ethynyl]-1,3,4-oxadiazole 
• 1221576-89-1 2-(4-trifluoromethylphenylethynyl)-5-methylbenzoxazole 
• 1221576-99-3 2-(4-trifluoromethylphenyl)ethynyl-4,4-dimethyloxazoline 
• 916496-45-2 2,5-bis(4-(trifluoromethyl)phenyl)furan 
• 1403688-96-9 N¹,N¹,N³,N³-tetraethyl-7-(trifluoromethyl)-2-(4-(trifluoromethyl)phenyl)naphthalene-1,3-diamine 
• 1432045-52-7 3-methyl-1,3-diphenyl-6-(4-(trifluoromethyl)phenyl)-5-hexyn-1-one 
• 1426841-25-9 2,2-dimethyl-4-(4-(trifluoromethyl)phenyl)but-3-ynenitrile 
• 1453300-00-9 1-benzyl-4-bromo-5-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazole 
• 383-53-9 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone 
• 1611483-84-1 1-(chlorobuta-1,3-diyn-1-yl)-4-(trifluoromethyl)benzene 

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.

Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution

The triazole heterocycle has been widely adopted as an isostere for the amide bond. Many native amides are α-chiral, being derived from amino acids. This makes α-N-chiral triazoles attractive building blocks. This report describes the first enantioselective triazole synthesis that proceeds via nickel-catalyzed alkyne-azide cycloaddition (NiAAC). This dynamic kinetic resolution is enabled by a spontaneous [3,3]-sigmatropic rearrangement of the allylic azide. The 1,4,5-trisubstituted triazole products, derived from internal alkynes, are complementary to those commonly obtained by the related CuAAC reaction. Initial mechanistic experiments indicate that the NiAAC reaction proceeds through a monometallic Ni complex, which is distinct from the CuAAC manifold.

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.

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.).

Catalytic Synthesis of Dibenzazepines and Dibenzazocines by 7-Exo- and 8-Endo-Dig-Selective Cycloisomerization

The 7-exo- and 8-endo-dig-selective gold-catalyzed cycloisomerizations of 2-propargylamino biphenyl derivatives were developed. The reaction of terminal alkynes gave dibenzo[b,d]azepines by 7-exo-dig cycloisomerization. In contrast, when internal alkynes were subjected to the reaction, 8-endo-dig cycloisomerization proceeded to provide dibenzo[b,d]azocines. The nucleophilicity at the reaction site and the electron-withdrawing effect of a tosyl group were important for the present selective transformation. This protocol could be used for ynamide substrates and a silver-catalyzed reaction gave 7-exo-dig products selectively.

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.).

Monobrominated alkyne compound, preparation method and application thereof

The invention belongs to the technical field of synthetic chemistry and discloses a monobrominated alkyne compound, a preparation method and an application thereof. The chemical structure formula of the monobrominated alkyne compound is as follows, wherei

Gold-Catalyzed C(sp2)?C(sp) Coupling by Alkynylation through Oxidative Addition of Bromoalkynes

A gold(I)-catalyzed cascade cyclization–alkynylation of allenoates using alkynyl bromide to generate β-alkynyl-γ-butenolides was investigated. Whereas alkynyl iodides afforded significant amounts of the homo-coupling of two lactone units, alkynyl bromides led to a selective reaction, and a broad functional group tolerance was observed. Under the optimized reaction conditions, it was possible to directly synthesize a large range of β-alkynyl-γ-butenolides in moderate to good yields without the need for any external oxidant.

Sulfilimines as Versatile Nitrene Transfer Reagents: Facile Access to Diverse Aza-Heterocycles

We herein report the unprecedented synthesis of diverse biologically important aza-heterocycles by employing sulfilimines as nitrene transfer reagents. This class of sulfur-based aza-ylides had not been successfully used for gold nitrene transfer before. This work contains an efficient generation of α-imino gold carbenes by N?S cleavage of sulfilimines. These gold carbenes undergo C?H insertion, cyclopropanation, and nucleophilic attack to form indoles (44 examples), 3-azabicyclo[3.1.0]hexan-2-imines (24 examples), and imidazoles (3 examples). Our study represents a unique gold-catalyzed reaction between alkynes and sulfur ylides, and also includes the first aza-heterocycle synthesis that proceeds by intermolecular nitrene transfer followed by cyclopropanation of the α-imino gold carbenes. Moreover, an unexpected synthesis of 4-acylquinolines (3 examples) from 2-acylphenyl sulfilimines and propargylic silyl ether derivatives by a 1,2-hydride shift onto the α-imino gold carbene and a subsequent Mukaiyama aldol cyclization was discovered.

Visible-Light-Promoted Oxo-Sulfonylation of Ynamides with Sulfonic Acids

A visible-light-promoted oxo-sulfonylation of ynamides with sulfonic acids is reported, giving rise to a collection of functionalized α-sulfonylated amides in a straightforward manner. The reaction proceeds sequentially through a cascade of electrophilic addition and photoinduced sulfonyl radical-sustained skeleton rearrangement. The high atom economy, mild reaction conditions, and wide substrate scope comprised the merits of this synthetic transformation.