16900-77-9

Upstream product

• 50-00-0 formaldehyd 
• 463-49-0 1,2-propanediene 
• 100-44-7 benzyl chloride 
• 107-19-7 propargyl alcohol 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 
• 104-53-0 3-phenyl-propionaldehyde 
• 119405-97-9 4-phenyl-1,1-dibromo-1-butene 
• 16520-62-0 4-Phenyl-1-butyne 

Downstream Products

• 75553-23-0 (E)-5-phenyl-2-penten-1-ol 
• 39520-63-3 (Z)-5-phenylpent-2-en-1-ol 
• 639006-01-2 (5-chloropent-3-yn-1-yl)benzene 
• 3350-93-4 5-phenyl-pent-2-ynoic acid 

Relevant academic research and scientific papers

Chiral Bifunctional Phosphine Ligand Enabling Gold-Catalyzed Asymmetric Isomerization of Alkyne to Allene and Asymmetric Synthesis of 2,5-Dihydrofuran

The asymmetric isomerization of alkyne to allene is the most efficient and the completely atom-economic approach to this class of versatile axial chiral structure. However, the state-of-the-art is limited to tert-butyl alk-3-ynoate substrates that possess

Acid-catalyzed chirality-transferring intramolecular Friedel-Crafts cyclization of α-hydroxy-α-alkenylsilanes

Acid-catalyzed intramolecular Friedel-Crafts cyclization of optically active α-hydroxy-α-alkenylsilanes possessing a benzene ring (>99% ee) with TMSOTf as a Lewis acid gave enantio-enriched tetrahydronaphthalenes (up to 98% ee). The silyl group attached to the chiral carbon played a crucial role in the chirality transfer.

Stereoselective Alkyne Hydrohalogenation by Trapping of Transfer Hydrogenation Intermediates

A catalytically generated vinylcopper complex, the reactive intermediate of a copper(I)-catalyzed alkyne transfer hydrogenation, can be trapped by commercially available halogen electrophiles. In this manner, internal alkynes can stereoselectively be hydrohalogenated to the corresponding vinyl chlorides, bromides, and iodides.

Stereoselective Synthesis of Exocyclic Tetrasubstituted Vinyl Halides via Ru-Catalyzed Halotropic Cycloisomerization of 1,6-Haloenynes

Herein, a ruthenium-catalyzed cycloisomerization that transforms 1,6-haloenynes into 5-membered carbo- and heterocycles that bear exocyclic, stereodefined, tetrasubstituted vinyl halides is reported. The reaction is insensitive to air and water, tolerates a variety of functional groups, and proceeds with good to excellent stereoselectivity and yield.

Regioselective Ni-Catalyzed Carboxylation of Allylic and Propargylic Alcohols with Carbon Dioxide

An efficient Ni-catalyzed reductive carboxylation of allylic alcohols with CO2 has been successfully developed, providing linear β,γ-unsaturated carboxylic acids as the sole regioisomer with generally high E/Z stereoselectivity. In addition, the carboxylic acids can be generated from propargylic alcohols via hydrogenation to give allylic alcohol intermediates, followed by carboxylation. A preliminary mechanistic investigation suggests that the hydrogenation step is made possible by a Ni hydride intermediate produced by a hydrogen atom transfer from water.

Copper-catalyzed C-C bond-forming transformation of CO2 to alcohol oxidation level: Selective synthesis of homoallylic alcohols from allenes, CO2, and hydrosilanes

A highly selective carbon-carbon bond-forming transformation of carbon dioxide (CO2) to alcohol oxidation level has been disclosed. By employing a copper/bisphosphine catalyst system and hydrosilanes as mild and easy-to-handle reducing agents,

Rhodium-catalyzed hydroformylation of 1,1-disubstituted allenes employing the self-assembling 6-DPPon system

Abstract A rhodium-catalyzed hydroformylation of 1,1-disubstituted allenes is reported. Using a RhI/6-DPPon catalyst system, one can obtain β,γ-unsaturated aldehydes in high regio- and chemoselectivity. The Z-configured product is formed with up to >95% selectivity when unsymmetrically 1,1-disubstituted allenes are submitted to the reaction conditions. This is the first time that these interesting building blocks are accessible by hydroformylation of allenes. The utility of this methodology is demonstrated by further transformations of one of the obtained products. β,γ-Unsaturated aldehydes are obtained by a rhodium-catalyzed hydroformylation of 1,1-disubstituted allenes. For unsymmetrically 1,1-disubstituted allenes the Z-configured product is formed in up to about 95% selectivity. This is the first time that these building blocks are accessible by hydroformylation of allenes. The utility of this methodology is demonstrated by further transformations of one of the obtained products.

Enantioselective iodolactonization of allenoic acids

An enantioselective iodolactonization reaction of allenoic acids has been developed using a trisimidazoline catalyst and I2. Our mechanistic study suggests the involvement of a π-allyl cation intermediate in this reaction system. This journal is

An efficient partial reduction of α,β-unsaturated esters using DIBAL-H in flow

The partial reduction of α,β-unsaturated esters and benzoate derivatives to form the corresponding aldehydes was achieved using a flow reactor system within 1 s at a high flow rate (18 mL min-1) under cryogenic conditions (-97°C). Commercially available diisobutylaluminium hydride (DIBAL-H) was used as the reductant. The desired enals and benzaldehyde derivatives, except for 4-methoxycinnamate and 4-methoxybenzoate, were formed selectively and redox economically in moderate to high yields.

Synthesis of substituted 3-hydroxy-2-furanone derivatives via an unusual enolate wittig rearrangement/alkylative cyclization sequence

Treatment of methyl O-(alkynylmethyl) glycolate derivatives with dialkylboron triflates and Huenig's base leads to the formation of highly substituted 3-hydroxy-2-furanone derivatives. The transformations appear to proceed via an unusual mechanism involving initial 2,3-Wittig rearrangement of a boron ester enolate followed by an alkylative cyclization reaction that leads to incorporation of an alkyl group from the boron reagent into the product.