184370-64-7

Upstream product

• 16520-62-0 4-Phenyl-1-butyne 
• 104-53-0 3-phenyl-propionaldehyde 
• 18328-11-5 3-benzyl propionaldehyde 
• 506-68-3 bromocyane 
• 119405-97-9 4-phenyl-1,1-dibromo-1-butene 

Downstream Products

• 218902-81-9 (Z)-(4-iodobut-3-en-1-yl)benzene 
• 184370-59-0 (E)-1-iodo-4-phenyl-1-butene 
• 474454-66-5 1-methoxymethoxy-2-[(1E)-4-phenylbut-1-eney]-4-nitrobenzene 
• 902760-14-9 9-phenylnonane-4,6-diynoic acid 
• 62692-41-5 (Z)-(4-bromobut-3-en-1-yl)benzene 
• 902760-31-0 9-phenylnonane-4,6-diynoic acid chloride 
• 474454-67-6 2-[(1E)-4phenylbut-1-enyl]-4-aminophenol 
• 138034-95-4 (C₆H₅C₂H₄)(H)C₂(H)Sn(C₄H₉)3 
• 1190789-03-7 1-(4-phenylbut-1-yn-1-yl)pyrrolidin-2-one 
• 1206483-02-4 C₁₉H₁₅NO 
• 1332480-54-2 C₂₂H₂₆NO₃P 
• 1426841-31-7 2,2-dimethyl-6-phenylhex-3-ynenitrile 
• 1344730-61-5 (E)-hex-1-en-3-yne-1,6-diyldibenzene 
• 1449689-70-6 (E)-3-phenyl-4-styryl-1,2-dihydronaphthalene 

Relevant academic research and scientific papers

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.

Selectivity for Alkynyl or Allenyl Imidamides and Imidates in Copper-Catalyzed Reactions of Terminal 1,3-Diynes and Azides

Copper-catalyzed reactions of terminal 1,3-diynes with electron-deficient azides to generate either 3-alkynyl or 2,3-dienyl imidamides and imidates are described. The selectivity depends on the diyne substituents and the nucleophile that reacts with the ketenimide intermediate generated from the corresponding triazole precursor. Reactions of 1,3-diynes containing a propargylic acetate afford [3]cumulenyl imidamides, while reactions using methanol as the trapping agent selectively generate 2,3-dienyl imidates. Five-membered heterocycles were obtained from 1,3-diynes containing a homopropargylic hydroxyl or amine substituent.

Versatile Access to Tetrasubstituted 2-Amidoacroleins through Formal Silylformylation of Ynamides

In this paper we are reporting the first regio- and stereoselective silylformylation of ynamides. This reaction is tolerant to a wide range of functional groups around the ynamides. The substitution of CO by an isocyanide makes this reaction safer and mor

Gold-Catalyzed Hydrofluorination of Internal Alkynes Using Aqueous HF

The gold-catalyzed hydrofluorination reaction of internal alkynes using hydrofluoric acid is reported. Notably, those conditions use one of the most economical sources of HF and are free of additional additives. Both symmetrical and unsymmetrical internal alkynes can be utilized, and the use of alkynes bearing a fluorinated group at the propargylic position as substrates allowed for a regioselective hydrofluorination reaction.

Chloramine Salt Mediated Oxidative Halogenation of Terminal Alkynes with KI or NaBr: Practical Synthesis of 1-Bromoalkynes and 1-Iodoalkynes

A direct oxidative halogenation of terminal alkynes has been realized using chloramine-B as the oxidant and KI or NaBr as the halogen source. This reaction enables a general and practical access to synthetically valuable 1-bromoalkynes and 1-iodoalkynes i

Copper-Catalyzed Alkynylboration of Alkenes with Diboron Reagents and Bromoalkynes

An efficient method for the synthesis of homopropargylboronates by copper-catalyzed alkynylboration of alkenes with diboron reagents and bromoalkynes has been developed. The alkynylboration reaction features high selectivity and efficiency, mild reaction conditions, wide substrate scope, and functional-group compatibility, and is a highly attractive complement to existing methods for the synthesis of homopropargylboronates. Both the boryl and alkynyl groups are good potential functional groups for the subsequent manipulations that provide access to a variety of important molecule structures.

Alkyne aminohalogenation enabled by DBU-activated N-haloimides: Direct synthesis of halogenated enamines

Activated by DBU, N-haloimides can be used as both halogen and nitrogen sources to achieve the difunctionalization of terminal alkynes, giving rise to useful halogenated enamines with high efficiency and high regio- and stereoselectivities. The cascade re

Facile and efficient synthesis of 1-haloalkynes via DBU-mediated reaction of terminal alkynes and N-haloimides under mild conditions

Directly from terminal alkynes and with N-halosuccinimides (halo = Br and I) or N-cholorophthalimide as the halogen sources, DBU as the activator, 1-haloalkynes were prepared in good to excellent yields at room temperature. Bis(bromoalkyne) and bis(iodoal

Copper-catalyzed cross-coupling of vinylsiloxanes with bromoalkynes: Synthesis of enynes

Enynes are versatile building blocks in organic synthesis. A copper-catalyzed Hiyama-type cross-coupling of vinylsiloxanes with bromoalkynes is presented. This mild and efficient method led to the formation of various sensitive enynes. The use of cis, trans, and 1,1′-disubstituted vinylsiloxanes was allowed, and full retention of stereochemistry was observed. Sensitive groups such as halides, unsaturated ketones, and aldehydes were fully tolerated.

Copper catalyzed decarboxylative alkynylation of quaternary α-cyano acetate salts

Cu-catalyzed decarboxylative alkynylation of quaternary α-cyano acetate salts with alkynyl bromides and alkynyl chlorides is described. This new reaction can be used for preparing functionalized butynenitrile derivatives.