494844-63-2

Upstream product

• 494844-61-0 3-phenyl-4-(1-phenylbut-3-enyl)isoxazol-5(2H)-one 
• 1817-49-8 1,3-diphenyl-1-propyn-3-ol 
• 762-72-1 allyl-trimethyl-silane 
• 93321-44-9 1,3-diphenylprop-2-yn-1-yl acetate 
• 128812-07-7 (R)-1,3-diphenylprop-2-yn-1-ol 
• 7338-94-5 1,3-diphenyl-2-propynone 
• 100-52-7 benzaldehyde 
• 536-74-3 phenylacetylene 
• 6738-06-3 phenylethynylmagnesium bromide 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 106-95-6 allyl bromide 
• 932-88-7 1-iodo-2-phenylethyne 
• 1088-32-0 3-phenyl-4-(1-phenylmethylidene)-5-isoxazolone 

Downstream Products

• 1007605-63-1 (1-(4-phenylcyclobut-1-enyl)vinyl)benzene 

Relevant academic research and scientific papers

Catalaytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenes

The cycloisomerization of 1,5-enynes catalyzed by cationic triphenylphosphinegold(I) complexes produces bicyclo[3.1.0]hexenes. Substitution at all positions of the 1,5-enyne is tolerated, leading to a wide range of bicyclo[3.1.0]hexane structures, includi

Michael Addition of Soft Carbon Nucleophiles to Alkylidene Isoxazol-5-ones: A Divergent Entry to β-Branched Carbonyl Compounds

A novel, divergent strategy toward the synthesis of β-branched (and linear) carbonyl compounds is developed by taking advantage of alkylidene isoxazol-5-ones as key building blocks. The yields obtained range from good to excellent, therefore making the described methods attractive options for building such molecules. (Chemical Equation).

Relay redox and Lewis acid catalysis in the titanocene- catalyzed multicomponent assembly of 1,5-enynes

Herein we describe a direct, multicomponent assembly of 1,5-enynes. The titanocene-catalyzed coupling of an aryl aldehyde, iodoalkyne, and allylsilane enables the convergent and rapid synthesis of this versatile architectural motif in good to excellent yields. Copyright

Facile coupling of propargylic, allylic and benzylic alcohols with allylsilane and alkynylsilane, and their deoxygenation with Et3SiH, catalyzed by Bi(OTf)3 in [BMIM][BF4] ionic liquid (IL), with recycling and reuse of the IL

Allyltrimethylsilane (allyl-TMS) reacts with propargylic alcohols 1a-1d in the presence of 10% Bi(OTf)3 in [BMIM][BF4] solvent to furnish the corresponding 1,5-enynes in respectable isolated yields (87-93%) at room temperature. The utility of Bi(OTf)3 as a superior catalyst was demonstrated in a survey study on coupling of allyl-TMS with 1a employing several metallic triflates (Bi, Ln, Al, Yb) as well as, B(C6F 5)3, Zn(NTf2)2 and Bi(NO 3)3·5H2O. Coupling of cyclopropyl substituted propargylic alcohol 1e with allyl-TMS gave the skeletally intact 1,5-enyne and a ring opened derivative as a mixture. Coupling of propargylic/allylic alcohol 1f with allyl-TMS resulted in allylation at both benzylic (2 isomers) and propargylic positions, as major and minor products respectively. The scope of this methodology for allylation of a series of allylic and benzylic alcohols was explored. Chemoselective reduction of a host of propargylic, propagylic/allylic, bis-allylic, allylic, and benzylic alcohols with Et3SiH was achieved in high yields with short reaction times. The same approach was successfully applied to couple representative propargylic and allylic alcohols with 1-phenyl-2-trimethylsilylacetylene. The recovery and reuse of the ionic liquid (IL) was gauged in a case study with minimal decrease in isolated yields after six cycles.

HClO4-supported on silica gel: A mild and efficient catalyst for Hosomi-Sakurai reaction

Perchloric acid supported on silica gel was found to be an efficient catalyst (2 mol %) for the Hosomi- Sakurai allylation of numerous aldehydes with allyltrimethylsilane in the presence of benzyl alcohol. This method was also effective for the allylation of secondary alcohols under mild experimental conditions.

Calcium-catalyzed direct coupling of alcohols with organosilanes

A calcium-catalyzed direct substitution of π-activated alcohols with different organosilanes under very mild reaction conditions is presented. The high reactivity of the calcium catalyst allows efficient conversion of secondary and tertiary allylic, secondary benzylic, and tertiary propargylic alcohols with allyltrimethylsilane at room temperature. Furthermore, the first direct substitution of an alcohol with (E)- as well as (Z)-alkenylsilanes was achieved under mild reaction conditions. Copyright

Gold(III)-catalyzed direct nucleophilic substitution of propargylic alcohols

Gold-catalyzed nucleophilic substitution of propargylic alcohols with various nucleophiles (allylsilane, electron-rich aromatics, alcohols, thiols, hydrides, 1,3-dicarbonyl derivatives, sulfonamides) is described under very mild conditions (room temperatu

Zinc-mediated allylation of aryl 2-propynyl acetates: A facile synthesis of 1,5-enynes

Aryl 2-propynyl acetates undergo smooth allylation with allylzinc bromide (generated in situ from allyl bromide and zinc metal) in THF at room temperature under mild conditions to furnish the corresponding 1,5-enynes in good to excellent yields and with high selectivity. Indium metal is also found to accomplish the nucleophilic substitution of aryl 2-propynylic acetates with allyl bromide. Copyright

Copper(II)-catalyzed allylation of propargylic and allylic alcohols by allylsilanes: a facile synthesis of 1,5-enynes

Propargylic alcohols undergo smooth deoxygenative allylation with allylsilanes in the presence of a solution of 10 mol % of copper(II) tetrafluoroborate in acetonitrile to afford the corresponding 1,5-enynes in good to high yields under mild and neutral c

PMA-SiO2: A heterogenous catalyst for O-, S-, and N-nucleophilic substitution reactions of aryl propargyl alcohols

Aryl-propargylic alcohols undergo O-, S-, and N-nucleophilic substitution reactions in the presence of a catalytic amount of PMA-SiO2. Copyright Taylor & Francis Group, LLC.