852525-81-6

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 693-02-7 hex-1-yne 

Downstream Products

• 903512-09-4 1-o-tolylhept-2-ynyl acetate 
• 1138140-72-3 1-(hept-2-ynyl)-2-methylbenzene 
• 1007605-45-9 1-(dec-1-en-5-yn-4-yl)-2-methylbenzene 
• 1238187-49-9 5-butyl-2-(phenylsulfonyl)-3-o-tolyl-2,3-dihydroisoxazole 
• 1644494-01-8 1-(o-tolyl)hept-2-yn-1-yl 3,4-dihydro-2H-pyran-6-carboxylate 
• 862250-84-8 1-(o-tolyl)-2-heptyn-1-one 

Relevant academic research and scientific papers

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.].

Synthesis of Vinyl-, Allyl-, and 2-Boryl Allylboronates via a Highly Selective Copper-Catalyzed Borylation of Propargylic Alcohols

An efficient methodology for the synthesis of vinyl-, allyl-, and (E)-2-boryl allylboronates from propargylic alcohols via Cu-catalyzed borylation under mild conditions is reported. In the presence of commercially available Cu(OAc)2 or Cu(acac)2 and Xantphos, the reaction affords the desired products in up to 92% yield with a broad substrate scope (43 examples). Isolation of an allenyl boronate as the reaction intermediate suggests that an insertion-elimination-type reaction, followed by borylcupration, is involved in the borylation of propargylic alcohols.

Highly diastereoselective synthesis of cyclopentenones via a one-pot gold catalysis, Nazarov cyclization and alkylation cascade

Starting from readily available propargylic carboxylates, three sequential transformations [gold-catalyzed tandem reaction, scandium(III) trifluoromethanesulfonate catalyzed Nazarov cyclization, alkylation reaction] in a one-pot process led to the formation of cyclopentenone derivatives in excellent diastereoselectivities and moderate to good overall yields. Georg Thieme Verlag Stuttgart. New York.

[(NHC)AuI]-catalyzed formation of conjugated enones and enals: An experimental and computational study

The [(NHC)AuI]-catalyzed (NHC = N-heterocyclic carbene) formation of α,β-unsaturated carbonyl compounds (enones and enals) from propargylic acetates is described. The reactions occur at 60°C in 8 h in the presence of an equimolar mixture of [(NHC)AuCl] and AgSbF6 and produce conjugated enones and enals in high yields. Optimization studies revealed that the reaction is sensitive to the solvent, the NHC, and, to a lesser extent, to the silver salt employed, leading to the use of [(ItBu)AuCl]/ AgSbF6 in THF as an efficient catalytic system. This transformation proved to have a broad scope, enabling the stereoselective formation of (E)-enones and -enals with great structural diversity. The effect of substitution at the propargylic and acetylenic positions has been investigated, as well as the effect of aryl substitution on the formation of cinnamyl ketones. The presence or absence of water in the reaction mixture was found to be crucial. From the same phenylpropargyl acetates, anhydrous conditions led to the formation of indene compounds via a tandem [3,3] sigmatropic rearrangement/intramolecular hydroarylation process, whereas simply adding water to the reaction mixture produced enone derivatives cleanly. Several mechanistic hypotheses, including the hydrolysis of an allenol ester intermediate and SN2′ addition of water, were examined to gain an insight into this transformation. Mechanistic investigations and computational studies support [(NHC)AuOH], produced in situ from [(NHC)AuSbF6] and H 2O, instead of cationic [(NHC)AuSbF6] as the catalytically active species. Based on DFT calculations performed at the B3LYP level of theory, a full catalytic cycle featuring an unprecedented transfer of the OH moiety bound to the gold center to the C≡C bond leading to the formation of a gold-allenolate is proposed.

AuI-catalyzed tandem [3,3] rearrangement-intramolecular hydroarylation: Mild and efficient formation of substituted indenes

(Chemical Equation Presented) Dignified auration: The rearrangement of phenylpropargyl acetates to substituted indenes is catalyzed by [Au 1(NHC)] complexes (see scheme, NHC = N-heterocyclic carbene) under extremely mild reaction conditions. This chemoselective transformation involves 1,3-migration of the acetate group and is proposed to proceed through an allene intermediate. TMS = trimethylsilyl, TBS = tert-butyldimethylsilyl.

Rhodium-catalyzed addition of arylzinc reagents to aryl alkynyl ketones: Synthesis of β,β-disubstituted indanones

(Chemical Equation Presented) A rhodium-catalyzed addition of arylzinc reagents to aryl alkynyl ketones for the synthesis of highly substituted indanones has been developed. The key to success has proved to be a proper choice of the reaction system, which involves the employment of dppf as a ligand and 1,2-dichloroethane as a solvent.