22489-95-8

Upstream product

• 106-96-7 propargyl bromide 
• 101-41-7 benzeneacetic acid methyl ester 

Downstream Products

• 910311-20-5 methyl 3-methyl-5-oxo-1-phenylcyclohex-3-ene-1-carboxylate 
• 1436872-14-8 methyl 2-phenyl-(5-phenyl-2-(3-phenylprop-2-ynyl))pent-4-ynoate 
• 1436872-15-9 methyl 5-(4-chlorophenyl)-2-(3-(4-chlorophenyl)prop-2-ynyl)-2-phenylpent-4-ynoate 
• 22489-94-7 2-phenyl-2-(prop-2-yn-1-yl)pent-4-yn-1-ol 
• 1436871-89-4 2,5-diphenyl-2-(3-phenylprop-2-ynyl)pent-4-ynoic acid 
• 1436871-90-7 5-(4-chlorophenyl)-2-(3-(4-chlorophenyl)prop-2-ynyl)-2-phenylpent-4-ynoic acid 
• 1436871-99-6 (R,E)-5-(bromomethylene)-3-phenyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one 
• 1451053-63-6 5-(4-bromophenyl)-2-(3-(4-bromophenyl)prop-2-ynyl)-2-phenylpent-4-ynoic acid 
• 1451053-65-8 2-phenyl-5-o-tolyl-2-(3-o-tolylprop-2-ynyl)pent-4-ynoic acid 

Relevant academic research and scientific papers

A Rh(I)-Catalyzed Cascade Cyclization of 1,5-Bisallenes and Alkynes for the Formation of cis-3,4-Arylvinyl Pyrrolidines and Cyclopentanes

The cascade cyclization reactions of 1,5-bisallenes grant access to a great variety of products by precisely tuning the catalyst system and/or the reagents involved. Herein, we present our findings that 1,5-bisallenes react with two molecules of dimethyl acetylenedicarboxylate to afford, in a completely diastereoselective manner, cis-3,4-arylvinyl pyrrolidines and cyclopentanes. DFT calculations have been used to postulate a mechanism for the developed reaction which encompasses a [2+2+2] cycloaddition reaction of the two alkynes and the external double bond of one allene, followed by a cycloisomerization involving the internal double bond of the second allene. (Figure presented.).

Synthesis of Fused Dihydroazepine Derivatives of Fullerenes by a Rh-Catalyzed Cascade Process

A synthetic methodology is reported that functionalizes C60 and C70 fullerenes with dihydroazepine rings by a cascade reaction encompassing a rhodium-catalyzed cycloisomerization of 1,5-bisallenes and a [4+2] cycloaddition. This tran

Desymmetrization construction of chiral lactones by synergistic Cu(II) complex and organic base

A highly enantioselective construction of quaternary carbon center has been realized by the desymmetrization strategy. Chiral enol lactones with up to 95% ee could be synthesized from prochiral dialkynoic acid under the catalysis of synergistic chiral Cu(II) complex and chiral (DHQ)2-PHAL base.

Palladium-catalyzed silaborative carbocyclizations of 1,6-diynes

An addition/cyclization reaction of 1,6-diynes was developed for the synthesis of highly substituted 1,2-dialkylidenecycloalkanes. In this work, 1,6-diynes reacted with (dimethylphenylsilyl)pinacol-borane in the presence of a palladium catalyst to afford 1,2-dialkylidenecycloalkanes bearing silyl and boryl groups with a (Z,Z)-configuration in good to excellent yields. Moreover, the corresponding products could be easily converted into other synthetically useful compounds. This protocol provides an efficient and practical method of heteroelement-element linkage addition to the unsaturated 1,6-diynes.

Enantioselective, desymmetrizing bromolactonization of alkynes

Asymmetric bromolactonizations of alkynes are possible using a desymmetrization approach. The commercially available catalyst (DHQD) 2PHAL promotes these cyclizations in combination with cheap NBS as a bromine source to give bromoenol lactones in high yield and with high enantioselectivity. The bromoenol lactone products, containing a tetrasubstituted alkene and a quaternary stereocenter, are valuable building blocks for synthetic chemistry.

Pd(ii)-SDP-catalyzed enantioselective 5-exo-dig cyclization of γ-alkynoic acids: Application to the synthesis of functionalized dihydofuran-2(3H)-ones containing a chiral quaternary carbon center

The Pd(ii)-SDP-catalyzed first enantioselective intramolecular cyclization of α,α-disubstituted γ-alkynoic acids is described. This 5-exo-dig cyclization afforded dihydrofuran-2(3H)-ones bearing a chiral quaternary carbon center in excellent yields with e

Cyclization/hydrosilylation of functionalized 1,6-diynes catalyzed by cationic platinum complexes containing bidentate nitrogen ligands

A 1:1 mixture of the platinum dimethyl diimine complex [PhN=C(Me)C(Me)=NPh]PtMe2 (4a) and B(C6F5)3 catalyzed the cyclization/hydrosilylation of dimethyl dipropargylmalonate (1) and HSiEt3 to form 1,1-dicarbomethoxy-3-methylene-4-(triethylsilylmethylene)cyclopentane (3) in 82% isolated yield with 26:1 Z:E selectivity. Platinum-catalyzed diyne cyclization/hydrosilylation tolerated a range of functional groups including esters, sulfones, acetals, silyl ethers, amides, and hindered ketones. Diynes that possessed propargylic substitution underwent facile cyclization/hydrosilylation to form silylated 1,2-dialkylidene cyclopentanes as mixtures of regioisomers. Diynes that possessed an electron-deficient internal alkyne underwent cyclization/hydrosilylation in moderate yield to form products resulting from silyl transfer to the less substituted alkyne. The silylated 1,2-dialkylidenecyclopentanes formed via diyne cyclization/hydrosilylation underwent a range of transformations including protodesilylation, Z/E isomerization, and [4 + 2] cycloaddition with dieneophiles.

Cyclization/Hydrosilylation of Functionalized Diynes Catalyzed by a Cationic Platinum Phenanthroline Complex

(Equation Presented) A 1:1 mixture of the platinum phenanthroline complex (phen)PtMe2 and B(C6F5)3 catalyzed the cyclization/hydrosilylation of functionalized 1,6- and 1,7-diynes to form silylated 1,2-dialkylide