16330-23-7

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 75-56-9 methyloxirane 
• 536-74-3 phenylacetylene 
• 4440-01-1 lithium phenylacetylide 
• 5689-83-8 4-methyl-[1,3,2]dioxathiolane 2,2-dioxide 
• 2117-11-5 4-pentyn-2-ol 
• 2001-45-8 tetraphenyl phosphonium chloride 
• 591-50-4 iodobenzene 
• 109-77-3 malononitrile 

Downstream Products

• 54985-34-1 trans-1-phenyl-1-penten-3-ol 
• 74143-89-8 5-phenyl-3,4-pentadien-2-one 
• 101028-21-1 (Z)-1,4-Dioxo-1-phenyl-2-pentene 
• 1046054-45-8 (E)-4-iodo-5-phenylpent-4-en-2-ol 
• 27927-59-9 4-hydroxy-1-phenylpentan-1-one 
• 131067-17-9 (E)-2-(1-methoxy-1-phenylmethylidene)-4-methyl-γ-butyrolactone 
• 4457-59-4 (2R*,5S*)-2-methyl-5-phenyltetrahydrofuran 
• 4457-59-4 tetrahydro-2-methyl-5-phenylfuran 
• 54985-29-4 (Z)-5-Phenyl-4-penten-2-ol 
• 2344-71-0 5-phenylpentan-2-ol 
• 1384458-53-0 (E)-5-phenylpent-4-en-2-yl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

A copper-catalyzed reaction between terminal alkynes, acetylenic esters, and oxiranes: efficient synthesis of 2H-pyran-4-carboxylate

Abstract: A catalytic reaction between terminal alkynes, acetylenic esters, and oxiranes has been described. This domino transformation serves as a useful sequential and one-pot method for the synthesis of 2H-pyran-4-carboxylate skeletons from the readily available starting materials. In situ-generated copper acetylides treated initially with oxiranes in the presence of copper catalysts and tetrabutylphosphonium salts, followed by addition of propiolates after 60?min to form synthetically important heterocycles. Graphic abstract: [Figure not available: see fulltext.]

Propylene glycol cyclic sulfate as a substitute for propylene oxide in reactions with acetylides

Lithium acetylides react cleanly with propylene glycol cyclic sulfate to give, after acidic hydrolysis, homopropargylic alcohols in good yield. The benzyl and TBDPS protecting groups are stable to these conditions, but the THP, TBS, acetal and orthoester groups are not. The readily available (S)-cyclic sulfate gives the (S)-alcohol without loss of stereochemical integrity.

Copper Salt Catalyzed Synthesis of Functionalized 2H-Pyranes

A copper-catalyzed reaction between terminal alkynes, oxiranes, and malonitrile has been described. In this transformation, copper acetylide was attacked on oxiranes to form homopropargyl alkoxy-copper intermediate that was further transferred to 2H-pyrane skeletons by reaction with malonitrile. We found that the reaction was not productive without hexafluoroisopropanol.

Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis

A distal-selective alkenyl C-H arylation method is reported through a directed palladium/norbornene (Pd/NBE) cooperative catalysis. The key is to use an appropriate combination of the directing group and the NBE cocatalyst. A range of acyclic and cyclic c

N-Methylpiperidine assisted catalytic multicomponent reaction

Abstract: A catalytic methodology involving terminal alkynes, elemental sulfur, and three-membered heterocycles has been described. This domino transformation serves as a useful method for the synthesis of oxathiolane and thiazolidine derivatives from the readily available starting materials. In situ generated copper acetylides reacted with elemental sulfur and oxiranes or aziridines in the presence of N-methylpiperidine as sulfur activating agent to form synthetically important heterocycles.

Method for synthesizing substituted furan

Provided is a method for synthesizing substituted furan. Iodohydrocarbon and terminal propargyl alcohol produce Sonogashira coupling reaction to generate an intermediate product 3-alkyne-1-alcohol, then isomeric cyclization occurs under the effect of Dess

Cu-catalyzed intramolecular aryl-etherification reactions of alkoxyl alkynes with diaryliodonium salts via cleavage of a stable C-O bond

A novel Cu-catalyzed intramolecular aryl-etherification reaction of alkoxyl alkynes with diaryliodonium salts is realized. The reactions proceed smoothly to produce valuable oxo-heterocycles with readily available linear starting materials via cleavage of a stable C-O bond. This journal is

A convergent general strategy for the functionalized 2-Aryl cycloalkylfused chromans: Intramolecular hetero-diels-alder reactions of ortho-quinone methides

(Figure Presented) Five and six: 3, 4-Cyclopentyl- and cyclohexyl-fused 2-arylchromans could be readily prepared from the intramolecular hetero-Diels-Alder reactions of the corresponding ortho-quinone methide (o-QM) precursors tethered to the styrenes under mild reaction conditions. The products were obtained with good to excellent diastereoselectivity (up to > 99:1 dr; see scheme; MOM = methoxymethyl).

Directed hydrozirconation of homopropargylic alcohols

Homopropargylic alcohols undergo directed hydrozirconation with Schwartz reagent (Cp2ZrHCl) to generate vinyl-metal species in which the metal fragment is proximal to the alkoxide. Electrophilic trapping yields tri-substituted olefins in good y

Cationic rhodium(I)/bisphosphane complex-catalyzed isomerization of secondary propargylic alcohols to α,β-enones

We have determined that hydrogenated cationic Rh(I)/bisphosphane complexes are highly active catalysts for the isomerization of secondary propargylic alcohols to α,β-enones. A kinetic resolution of secondary propargylic alcohols proceeded with moderate selectivity with [Rh((R)-BINA-P)]OTf as a catalyst. Mechanistic studies revealed that the isomerization proceeds through intramolecular 1,3- and 1,2-hydrogen migration pathways. The isomerization of propargylic diol derivatives was also investigated, which revealed that 1,4-diketones, furans, and α,β-enones were obtained from 2-butyn-1,4-diol, 1-methoxy-2-butyn-4-ol, and 1-acetoxy-2-butyn-4-ol derivatives, respectively. Furthermore, chemoselectivity of the isomerization of an acetylenic diol was investigated, and preferential oxidation of a propargylic hydroxy group was observed. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.