59738-52-2

Upstream product

• 1817-49-8 1,3-diphenyl-1-propyn-3-ol 
• 75-77-4 chloro-trimethyl-silane 
• 100-52-7 benzaldehyde 
• 536-74-3 phenylacetylene 
• 3757-88-8 tributylstannylethynylbenzene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 

Downstream Products

• 94-41-7 benzalacetophenone 
• 1167444-75-8 2-(naphthalen-2-yl)-1,3,5-triphenyl-1-H-pyrrole 
• 1167444-70-3 1-(4-iodophenyl)-2,3,5-triphenyl-1-H-pyrrole 
• 1167444-74-7 1,3,5-triphenyl-2-(4-(trifluoromethyl)phenyl)-1H-pyrrole 
• 1167444-73-6 methyl 4-(1,3,5-triphenyl-1-H-pyrrol-2-yl)benzoate 
• 15345-47-8 1,2,3,5-tetraphenyl-pyrrole 
• 96272-65-0 1-(4-metoxyphenyl)-2,3,5-triphenyl-1-H-pyrrole 
• 53842-18-5 1,3,5-triphenyl-2-(4-chlorophenyl)-1H-pyrrole 
• 1167444-72-5 2-(4-bromophenyl)-1,3,5-triphenyl-1-H-pyrrole 
• 1817-49-8 1,3-diphenyl-1-propyn-3-ol 
• 34877-78-6 4,6-diphenyl-hex-5-yn-2-one 
• 128812-07-7 (R)-1,3-diphenylprop-2-yn-1-ol 

Relevant academic research and scientific papers

Gold(I)-catalyzed bis-alkynylation reaction of aromatic aldehydes with alkynylsilanes

The first successful gold(I)-catalyzed reaction of aryl aldehydes with trimethyl(arylethynyl)silanes to furnish bis-alkynylated derivatives is reported. Key C-C bond-forming events involved in the catalytic cycle are analyzed. Copyright

Siloxyallenes revisited. A useful functional intermediate for the synthesis of (Z)-β-branched Morita-Baylis-Hillman type adducts and (Z)-chalcones

Siloxyallenes proved to be a useful functional intermediate in the preparation of (Z)-β-branched Morita-Baylis-Hillman type adducts by the reaction of aldehydes with silylacetylenes or siloxypropynes. Various (Z)-chalcones were stereoselectively synthesized from siloxypropynes via siloxyallenes.

Synthesis of β-branched Morita-Baylis-Hillman-type adducts from 1,3-diaryl-2-propynyl trimethylsilyl ethers and aldehydes catalyzed by potassium tert-butoxide

1,3-Diaryl-2-propynyl trimethylsilyl ethers were easy to isomerize into the corresponding siloxyallenes using a catalytic amount of potassium tert-butoxide under very mild conditions. The siloxyallenes reacted in situ with various aldehydes to afford Z-selective β-branched Morita-Baylis-Hillman-type adducts in a one-pot reaction after acid treatment.

Fluoride-ion-mediated reactions of trimethylsilylacetylene with carbonyl compounds and terminal acetylenes

Fluoride-ion-mediated reaction of trimethylsilylacetylene with carbonyl compounds has been thoroughly studied. The products of addition to the C=O bond were obtained in 15-66% yield, their subsequent silylation and addition to the second molecule of the c

Utilization of tetrabutylammonium triphenyldifluorosilicate as a fluoride source for silicon-carbon bond cleavage

Tetrabutylammonium triphenyldifluorosilicate (TBAT) can be employed as a fluoride source to cleave silicon-carbon bonds thus generating in situ carbanions that coupled with a variety of electrophiles, including aldehydes and ketones, in moderate to high yields. Among the examples reported is the first instance of fluoride-induced intermolecular coupling between allyltrimethylsilane and imine derivatives. Also, of particular note is the TBAT-initiated coupling of primary alkyl halides with allyltrimethylsilane. TBAT is an easily handled crystalline solid that has several advantages over tetrabutylammonium fluoride (TBAF) as a fluoride source; it is anhydrous, nonhygroscopic, soluble in most commonly used organic solvents, and less basic than TBAF.

Solvent-Controlled Addition of Alkynyltins or Allylic Tins to Aldehydes Catalyzed by Indium Trichloride

Indium trichloride promoted catalytically the addition of alkynyltins or allylic tins to aldehydes in two ways: transmetallation with the tin compounds and activation of aldehydes as a Lewis acid.The stereochemical outcome in the addition of cinnamylbutyl

FLUORIDE CATALYZED REACTION OF SILYLACETYLENES WITH CARBONYL COMPOUNDS

(Phenylethynyl)trimethylsilane undergoes nucleophilic addition to a variety of carbonyl compounds in the presence of a catalytic amount of fluoride anion to give silylated propargyl alcohol derivatives.The reaction fails with enolizable enones and cyclopentanone.The reaction of bis(trimethylsilyl)acetylene does not stop at the stage of monoadduct, and affords a considerable amount of symmetric bisadduct. (Trimethylsilyl)acetylene attacks 4-t-butylcyclohexanone from the axial side, as other metal acetylides do.Although much slower than the above cases, the reaction of alkynyltrimethylsilanes also proved successful.The reactivities of these (trimethylsilyl)-acetylenes are discussed in terms of the reaction mechanism and the nature of the reactive species, and also compared with those of the silylated enols under similar conditions.