3780-00-5

Upstream product

• 4980-70-5 1,3-diphenyl-1-propyne 
• 7785-26-4 (-)-α-pinene 
• 3780-00-5 1-(3-phenyl-1,2-propadienyl)benzene 
• 20431-64-5 (-)-Ethyl-N-(trans-2,3-diphenyl-cyclopropyl)-carbamat 
• 64788-21-2 1-Chloro-3-phenyl-1,2-propadien 
• 1078-58-6 diphenylzinc 
• 84681-19-6 (R)-(+)-1-phenyl-prop-2-yn-1-acetyloxy 
• 70000-50-9 Methanesulfinic acid (S)-1-phenyl-prop-2-ynyl ester 
• 4187-87-5 (R)-1-phenyl-2-propyn-1-ol 
• 946008-11-3 C₁₇H₁₄O₃ 
• 98-80-6 phenylboronic acid 
• 100-52-7 benzaldehyde 
• 536-74-3 phenylacetylene 
• 1133970-54-3 (S)-1-((S)-1,3-diphenylprop-2-yn-1-yl)-2-(pyrrolidin-1-ylmethyl)-pyrrolidine 

Downstream Products

• 848245-36-3 (S,E)-[(Cp)2Zr(N(2,6-Me₂C₅H₃)C(CHC₆H₅)CHC₆H₅)] 
• 3780-00-5 1-(3-phenyl-1,2-propadienyl)benzene 
• 17325-41-6 cis-1,2-Diphenyl-anti-3,4-dibenzylidenecyclobutane 
• 15408-55-6 4,4-Dichlor-1-phenyl-3-dichlormethylen-2-benzyliden-cyclobutan 
• 3780-00-5 (R)-1,3-diphenylallene 
• 41049-36-9 1-hydroxy-1,3-diphenylacetone 
• 42523-75-1 3-Chloro-benzoic acid 2-oxo-1,3-diphenyl-propyl ester 
• 86477-17-0 (3-methoxyprop-1-ene-1,3-diyl)dibenzene 
• 17325-41-6 C₃₀H₂₄ 
• 17325-41-6 C₃₀H₂₄ 
• 3412-44-0 1,3-diphenylpropene 
• 98-52-2 4-(1,1-dimethylethyl)-cyclohexanol 
• 19754-02-0 tetrabenzylethylene 

Relevant academic research and scientific papers

Room Temperature Allenation of Terminal Alkynes with Aldehydes

A gold-catalyzed room temperature allenation of terminal alkynes (ATA) with aldehydes affording 1,3-disubstituted allenes with diverse functional groups has been developed by identifying a gold(I) catalyst and an amine. The practicality of this reaction has been demonstrated by a ten gram-scale synthesis and the synthetic potentials have been demonstrated via various transformations and formal total synthesis of (?)-centrolobine. Mechanistic studies revealed that the gold catalyst, the aldehyde effect, the fluoroalkyl hydroxyl solvent (TFE or HFIP) and the structure of amine are vital in this room temperature ATA reaction.

Copper-Catalyzed 1,1-Boroalkylation of Terminal Alkynes: Access to Alkenylboronates via a Three-Component Reaction

A copper-catalyzed three-component reaction of terminal alkynes, diazo compounds, and B2pin2 to prepare trisubstituted alkenylboronates has been developed. This difunctionalization of alkynes selectively occurs at the terminal carbon atom and proceeds via

Trifluoromethylation of Allenes: An Expedient Access to α-Trifluoromethylated Enones at Room Temperature

A silver(I) catalyzed regioselective trifluoromethylation of allenes using Langlois's salt (NaOSOCF3) is demonstrated. This transformation enables direct expedient access to α-trifluoromethylated acroleins, which are valuable synthons for a number of pharmaceuticals and agrochemicals containing vinyl-CF3 moieties. Versatility of this trifluoromethylation method has been established with good yield and excellent regioselectivity. Preliminary experiments and computational studies were carried out to elucidate the mechanistic insight of this protocol.

A convenient access to allylic triflones with allenes and triflyl chloride in the presence of (EtO)2P(O)H

A simple method for the preparation of allylic triflones from allenes and triflyl chloride in the presence of (EtO)2P(O)H has been developed. The features of this reaction are catalyst-free and simple starting substrates. This method tolerates diverse functional groups and substituted allylic triflones are obtained in moderate to good yields.

Matched Coupling of Propargylic Carbonates with Cyclopropanols

The ring opening-coupling reaction of cyclopropanols with propargylic carbonates affording synthetically attractive allenyl ketones has been developed. The mechanism involves the ligand-exchange reaction of in situ formed allenyl palladium methoxide with cyclopropanols followed by carbon-carbon bond cleavage and reductive elimination. The reactions proceeded smoothly under mild reaction conditions with Pd(0)/XPhos catalysis in the absence of any external base and displayed a wide scope and application to a steroidal skeleton. The efficiency of chirality transfer and synthetic utility of the allene products have also been demonstrated.

Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of α-(Difluoromethyl)styrenes

Phenylallenes undergo fluorinative rearrangement upon the action of (difluoroiodo)toluene in the presence of 20 mol % BF3?OEt2 to yield α-difluoromethyl styrenes. This unprecedented reaction was entirely chemoselective for the internal allene π bond, and showed remarkable regioselectivity during the fluorination event. Substituted phenylallenes, phenylallenes possessing both phenyl- and α-allenyl substituents, and diphenylallenes were investigated, and good functional-group compatibility was observed throughout. The ease with which allenes can be prepared on a large scale, and the operational simplicity of this reaction allowed us to rapidly access fluorine-containing building blocks that have not been accessed by conventional deoxyfluorination strategies.

Stereoselective annulation between an allene, an alkene, and two nitrosoarenes to access bis(isoxazoliodine) derivatives

This work reports metal-free annulations between one allene, two nitrosoarenes and one electron-deficient alkene to afford bis(isoxazolidine) derivatives stereoselectively. This process involves an initial formation of isoxazolidin-4-imine oxides, followe

Iodothiocyanation/Nitration of Allenes with Potassium Thiocyanate/Silver Nitrite and Iodine

Direct strategies for the iodothiocyanation and iodonitration of allenes have been developed. In this process, potassium thiocyanate/silver nitrite and molecular iodine are used as the source of SCN, ONO2and iodine to provide the desired products in moderate to good yields with high stereoselectivity. (Figure presented.).

Enantioselective A3 Reactions of Secondary Amines with a Cu(I)/Acid-Thiourea Catalyst Combination

Pyrrolidine and related amines undergo asymmetric A3 reactions in the presence of copper iodide and an easily accessible cocatalyst possessing both a carboxylic acid and a thiourea moiety. Propargylamines are obtained with up to 96% ee, and catalyst loadings can be as low as 1 mol %. Pyrrolidine-derived propargylamines, in the absence of directing groups, can be transformed to the corresponding allenes without loss of enantiopurity.

Ligandless Regioselective Hydrosilylation of Allenes Catalyzed by Gold Nanoparticles

The first example of Au-catalyzed hydrosilylation of allenes is presented using recyclable gold nanoparticles as catalyst, without the requirement of any external ligands or additives. The hydrosilane addition takes place on the more substituted double bond of terminal allenes in a highly regioselective manner. The observed regioselectivity/reactivity modes are attributed to steric and electronic factors.