63124-66-3

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 925-90-6 ethylmagnesium bromide 
• 536-74-3 phenylacetylene 
• 4440-01-1 lithium phenylacetylide 
• 104-55-2 3-phenyl-propenal 
• 932-88-7 1-iodo-2-phenylethyne 
• 875877-88-6 (2E)-[[3-phenyl-1-(phenylethynyl)-2-propenyl]oxy]-trimethylsilane 
• 3883-13-4 2,2,2-trichloroethylbenzene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 

Downstream Products

• 17486-86-1 1,5-diphenylpentan-3-ol 
• 308848-57-9 3-(E)-(1,5-diphenyl-pent-1-en-4-ynyl)-i-butylcarbonate 
• 875877-88-6 (2E)-[[3-phenyl-1-(phenylethynyl)-2-propenyl]oxy]-trimethylsilane 
• 60839-95-4 2,6-diphenyl-2,3-dihydro-4H-thiopyran-4-one 
• 1000703-57-0 3-[(E)-3-phenyl-1-(2-phenylethynyl)allyl]-1H-indole 
• 1000703-58-1 3-[(E)-3-phenyl-1-(2-phenylethynyl)allyl]-1H-indole-5-carbonitrile 
• 1019840-34-6 C₃₈H₂₆ 
• 1019840-33-5 1,5-diphenyl-3-(2-phenylethynyl)pent-1-ene-4-yne 
• 1019840-36-8 C₁₉H₁₄ 
• 1019840-35-7 C₃₆H₂₆ 
• 1434337-03-7 (E)-2-phenyl-4-styrylpyrano[3,2-c]chromen-5(4H)-one 
• 1434338-50-7 (E)-3-(1,5-diphenylpent-2-en-4-ynyl)-4-hydroxy-2H-chromen-2-one 
• 1434336-96-5 (E)-2-phenyl-4-styryl-6,7-dihydrocyclopenta[b]pyran-5(4H)-one 
• 1434338-47-2 (E)-2-(1,5-diphenylpent-2-en-4-ynyl)-3-hydroxycyclopent-2-enone 

Relevant academic research and scientific papers

Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects

A detailed study has been completed on the asymmetric transfer hydrogenation (ATH) of a series of enones using Ru(II) catalysts. Electron-rich rings adjacent to the C[dbnd]O group reduce the level of C[dbnd]O reduction compared to C[dbnd]C. The ATH reaction can readily discriminate between double and triple bonds adjacent to ketones, reducing the double bond but leaving a triple bond intact in the major product.

Alkynylation of aldehydes mediated by zinc and allyl bromide: a practical synthesis of propargylic alcohols

Abstract: A practical synthesis of propargylic alcohols was developed by alkynylation of aldehydes mediated by zinc and allyl bromide. Aromatic, aliphatic and vinyl aldehydes react with phenylacetylene or 1-hexyne to obtain various propargylic alcohols at room temperature in up to 98% yield. This method is characterized with inexpensive materials, wide substrate scope, and mild reaction conditions, and is also easy to scale up. In addition, this protocol is applicable to the alkynylation of α-ketone esters and epoxides to generate α-tertiary-hydroxy esters and α-alkynyl alcohols, respectively. Graphical Abstract: [Figure not available: see fulltext.].

Oxidation of alcohols to carbonyl compounds with molecular iodine in the presence of potassium tert-butoxide

An efficient protocol for the oxidation of alcohols to carbonyl compounds with molecular iodine and potassium tert-butoxide is described. Various primary and secondary alcohols were converted to the corresponding aldehydes and ketones in high yields. The oxidation of 2-phenylethanol produced an "abnormal" acetalic ketone. The readily availability of starting materials, convenient synthetic procedure, operational simplicity, mild reaction conditions, and high yields makes this protocol a competitive alternative in the synthesis of ynones and ketones as well as aryl aldehydes.

A sulfur ylides-mediated domino benzannulation strategy to construct biaryls, alkenylated and alkynylated benzene derivatives

An efficient domino benzannulation strategy with the participation of sulfur ylides for the construction of biaryl compounds is disclosed. It could also be extended to the synthesis of alkenylated and alkynylated benzene derivatives under mild conditions. This versatile strategy combined with traditional metal-catalyzed cross-coupling methods should offer a practical route to construct complex multiaryl compounds.

Titanocene-catalyzed metallation of propargylic acetates in homopropargyl alcohol synthesis

The titanium-catalyzed metallation and subsequent carbonyl addition of propargylic acetates enable the direct formation of homopropargylic alcohols in good yields. The corresponding products were obtained as single regioisomers without the corresponding a

Catalytic asymmetric enyne addition to aldehdyes and Rh(I)-catalyzed stereoselective domino Pauson-Khand/[4 + 2] cycloaddition

The 1,1′-bi-2-naphthol-ZnEt2-Ti(OiPr) 4-Cy2NH system is found to catalyze the 1,3-enyne addition to aliphatic aldehydes as well as other aldehydes at room temperature with 75-96% yield and 82-97% ee. This system is also broadly applicable for the highly enantioselective reaction of other alkyl-, aryl-, and silylalkynes with structurally diverse aldehydes. The propargylic alcohols prepared from the catalytic asymmetric enyne addition to aliphatic aldehydes are used to prepare a series of optically active trienynes. In the presence of a catalytic amount of [RhCl(CO)2]2 and 1 atm of CO, the optically active trienynes undergo highly stereoselective domino Pauson-Khand/[4 + 2] cycloaddition to generate optically active multicyclic products. The Rh(I) catalyst is also found to catalyze the coupling of a diyne with CO followed by [4 + 2] cycloaddition to generate an optically active multicyclic product. These transformations are potentially useful for the asymmetric synthesis of polyquinanes containing a quaternary chiral carbon center.

Double gold-catalysed annulation of indoles by enynones

The gold-catalysed double functionalisation of indoles is presented. Enynones are used to annulate indoles via a double sodium tetrachloroaurate- catalysed process involving a mixture of C-H activation and alkyne activation modes of promotion. Good yields

Generation of nucleophilic chromium acetylides from gem-trichloroalkanes and chromium Chloride: Synthesis of propargyl alcohols

Nucleophilic mixed chromium(II) and chromium(III) acetylides are generated from the smooth reduction of primary 1,1,1-trichloroalkanes with chromium(II) chloride in the presence of an excess amount of triethylamine at room temperature. These species arise from chrornium(III) vinylidene carbenoids. It has been demonstrated that uncommon low-valent CrII acetylides are formed by C-H insertion of CrIICl2 into terminal alkynes, formed in situ through the FritschButtenberg-Wiechell (FBW) rearrangement, whereas CrIII acetylides are concomitantly generated by HCl elimination from the chromium(III) vinylidene carbenoid, Both divergent pathways result, overall, in the formation of nucleophilic acetylides. In situ trapping with electrophilic aldehydes afforded propargyl alcohols. Furthermore, deuteration experiments and the use of deuterium labeled 1,1,1-trichloroalkane substrates demonstrated the prevalence of low-valent Cr11 acetylides, potentially useful, yet highly elusive synthetic intermediates.

Reactivity of 3-silyloxy-1,4-enynes: Gold(III)-catalyzed regioselective nucleophilic substitution

Gold-catalyzed reactions of 3-silyloxy-1,4-enynes with alcohols afford primary, secondary, and tertiary pent-2-en-4-ynyl ethers in moderate to excellent yields. The substitution proceeds with high regioselectivity. An initial cyclization providing five-me