1463-04-3

Upstream product

• 591-50-4 iodobenzene 
• 78-80-8 2-methylbut-1-en-3-yne 
• 67-56-1 methanol 
• 160721-88-0 (Z)-2-Chloro-3-methyl-1-phenyl-1,3-butadiene 
• 7664-93-9 sulfuric acid 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 557-93-7 2-bromoprop-1-ene 
• 536-74-3 phenylacetylene 
• 77311-61-6 3-methyl-1-phenyl-3-buten-2-ol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 100-66-3 methoxybenzene 
• 61423-02-7 ethyl 1,1-dimethyl-3-phenylpropargyl acetate 
• 72410-67-4 tert-butyl 2-diazo-2-phenylacetate 

Downstream Products

• 54994-56-8 C₂₄H₂₀ 
• 55967-09-4 (3-Methyl-1,4-bis-trimethylsilanyl-buta-1,2-dienyl)-benzene 
• 55967-10-7 (3-methyl-1-phenyl-1,2-butadienyl)trimethylsialne 
• 124746-08-3 1-(2,2-dichloro-1-methylcyclopropyl)-2-phenylcyclopropenone 
• 7065-27-2 2-methyl-2-(2-phenylethynyl)oxirane 
• 1296172-80-9 1,4-diphenyl-3-methyl-2-butyn-3-ol 
• 1308661-40-6 C₁₈H₁₈O₃S 
• 1334049-19-2 diethyl 2-hydroxy-2-methyl-4-phenylbut-3-ynylphosphonate 
• 1016668-20-4 C₁₆H₁₆ 
• 69535-83-7 2,9,9-trimethyl-9H-fluorene 

Relevant academic research and scientific papers

Catalytic Enantioselective Synthesis of β-Allenyl Boronic Esters by Conjunctive Cross-Coupling with Propargylic Carbonates

Enantioselective conjunctive cross-coupling with propargylic carbonates affords β-boryl allenes as the reaction product. The reaction is found to proceed through the intermediacy of dimethoxyboronate complexes that are generated in situ by a strain-induce

Catalyst-Free Rearrangement of Allenyl Aryldiazoacetates into 1,5-Dihydro-4H-pyrazol-4-ones

Phenylpropargyl diazoacetates exist in equilibrium with 1-phenyl-1,2-dien-1-yl diazoacetate - allenes that are rapidly formed at room temperature through 1,3-acyloxy migration catalyzed by gold(I) or gold(III) compounds, and these catalysts react solely with the π-donor rather than with the diazo group. The product allene of the aryldiazoacetates undergoes rearrangement that is not catalyzed by gold in which the terminal nitrogen of the diazo functional group adds to the central carbon of the allene, initiating a sequence of bond-forming reactions, resulting in the production of 1,5-dihydro-4H-pyrazol-4-ones in good yields. These 1,5-dihydro-4H-pyrazol-4-ones undergo intramolecular 1,3-acyl migration to form an equilibrium mixture and can quantitatively transfer the acyl group to an external nucleophile with formation of 4-hydroxypyrazoles. Reactions of phenylpropargyl phenyldiazoacetates catalyzed by cationic gold complexes are initiated at the diazo functional group to form a gold carbene whose subsequent cascade process (intramolecular addition, then aromatic substitution) results in the formation of a product that is uniquely characteristic of this pathway.

Diverse Pathways in Catalytic Reactions of Propargyl Aryldiazoacetates: Selectivity between Three Reaction Sites

Three catalyst-dependent divergent reaction pathways for reactions of propargyl aryldiazoacetates are disclosed. Transition metal catalysts including those of rhodium(II), palladium(0 and II), silver(I), mercury(II), copper(I and II), platinum(II), and cationic gold(I) are effective for reactions that proceed through dinitrogen extrusion, carbene/alkyne metathesis, and aromatic substitution to form fused indeno-furanones, and use of tetrakis(acetonitrile)copper(I) provides indeno-furanones in the highest product yields. A Lewis acid catalyzed pathway that forms furan-2-ones is uncovered with FeCl3, ZnBr2, and BF3·Et2O as catalysts that proceed through activation of the aryldiazoacetate ester for arylpropargyl cation dissociation followed by recombination through cation addition to the diazo carbon. Neutral gold catalysts selectively activate the triple bond of propargyl aryldiazoacetates, resulting in the formation of allenic aryldiazoesters that further undergo uncatalyzed rearrangement.

Electrochemical fluorosulfonylation of styrenes

An environmentally friendly and efficient electrochemical fluorosulfonylation of styrenes has been developed. With the use of sulfonylhydrazides and triethylamine trihydrofluoride, a diverse array of β-fluorosulfones could be readily obtained. This reaction features mild conditions and a broad substrate scope, which could also be conveniently extended to a gram-scale preparation.

Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes

Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.

Dual Photoredox/Nickel-Catalyzed 1,4-Sulfonylarylation of 1,3-Enynes with Sulfinate Salts and Aryl Halides: Entry into Tetrasubstituted Allenes

A radical-mediated three-component 1,4-sulfonylarylation of 1,3-enynes with aryl iodides and sulfinate salts using cooperative photoredox/nickel catalysis is described. This protocol enables the synthesis of tetrasubstituted sulfonyl-containing allenes under redox-neutral conditions and provides a versatile 1,3-enyne 1,4-difunctionalization platform for the synthesis of a diverse range of tetrasubstituted allenes with high chemo- and regioselectivities, excellent functional group tolerance, and a broad substrate scope.

Stereo- And Regioselective cis-Hydrophosphorylation of 1,3-Enynes Enabled by the Visible-Light Irradiation of NiCl2(PPh3)2

Described herein is a stereo- and regioselective cis-hydrophosphorylation reaction of the internal alkyne of 1,3-enynes that accesses various 1,3-dienes in good isolated yields. The visible-light irradiation of NiCl2(PPh3)2 allows the generation of highly reactive nickel(II)-phosphorus species that subsequently migrate into the internal alkyne of the 1,3-enynes and protonate the resulting vinyl nickel species, leading to various phosphinoyl 1,3-butadienes under mild reaction conditions.

Gold catalyzed efficient preparation of dihydrobenzofuran from 1,3-enyne and phenol

A gold catalyzed formal intermolecular [2+3] cyclo-coupling of 1,3-enynes with phenols was developed to prepare dihydrobenzofuran derivatives with the addition of 2,6-dichloropyridine N-oxide, in which, a highly ortho-selective phenol SEAr functionalizati

Asymmetric Wacker-Type Oxyallenylation and Azaallenylation of Cyclic Alkenes

Palladium-catalyzed three-component carboetherification of cyclic alkenes proceeded to give trans adducts exclusively with excellent enantioselectivity through a Wacker-type pathway. The reaction is also applicable to other oxygen nucleophiles, such as water, phenols, and carboxylic acids, as well as some electron-poor aryl amines.

Fe-Catalyzed Selective Cyclopropanation of Enynes under Photochemical or Thermal Conditions

The nucleophilic Fe-complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the cyclopropanation of enynes to substituted propargyl cyclopropanes using diazoesters as carbene surrogates. The catalyst can be activated either thermally in the presence of catalytic amounts of 4-nitroanisole or under photochemical conditions. Cyclopropanation occurs selectively at the enyne moiety; alternative olefinic moieties remain intact.