17474-12-3

Upstream product

• 917-92-0 3,3-Dimethylbut-1-yne 
• 100-52-7 benzaldehyde 
• 66530-03-8 (3,3-dimethylbut-1-ynyl)dimethylaluminium 
• 104480-60-6 (3,3-dimethylbut-1-yn-1-yl)magnesium bromide 
• 23700-63-2 1-iodo-3,3-dimethylbut-1-yne 
• 62276-26-0 B-1-(3,3-dimethylbutynyl)-9-borabicyclo<3.3.1>nonane 
• 110-82-7 cyclohexane 
• 17475-11-5 1-phenyl-4,4-dimethylpent-2-yn-1-one 

Downstream Products

• 17475-11-5 1-phenyl-4,4-dimethylpent-2-yn-1-one 
• 866562-21-2 4,4-dimethyl-1-phenylpent-2-ynyl acetate 
• 106059-50-1 (Z)-4,4-Dimethyl-1-phenyl-pent-2-en-1-one 
• 29569-93-5 (E)-4,4-dimethyl-1-phenylpent-2-en-1-one 
• 538-44-3 4,4-dimethyl-1-phenyl-1-penten-3-one 
• 1196968-51-0 C₂₂H₂₅NO₂ 
• 1238187-64-8 5-tert-butyl-3-phenyl-2-(phenylsulfonyl)-2,3-dihydroisoxazole 
• 28435-47-4 (Z)-4,4-dimethyl-1-phenylpent-1-en-3-one 
• 538-44-3 (E)-benzylidenepinacolone 
• 1338443-25-6 (E)-2-(dimethyl(phenyl)silyl)-4,4-dimethyl-1-phenylpent-2-en-1-ol 
• 1388624-45-0 benzaldehyde O-(4,4-dimethyl-1-phenylpent-2-yn-1-yl)oxime 
• 203172-78-5 4,4-dimethyl-1-phenyl-2-pentyne 
• 16301-90-9 1-(diphenylphosphoryl)-4,4-dimethyl-1-phenylpentan-3-one 

Relevant academic research and scientific papers

Propargylation of CoQ0 through the Redox Chain Reaction

An efficient catalytic propargylation of CoQ0 is described by employing the cooperative effect of Sc(OTf)3 and Hantzsch ester. It is suggested to work through the redox chain reaction, which involves hydroquinone and dimeric propargylic moiety intermediates. A broad range of propargylic alcohols can be converted into the appropriate derivatives of CoQ0 containing triple bonds in good to excellent yields. The mechanism of the given transformation is also discussed.

Cascade and Effective Syntheses of Functionalized Tellurophenes

A one-pot and transition-metal-catalyst-free synthetic strategy to construct functionalized tellurophenes has been developed. Substituted 1,1-dibromo-1-en-3-ynes are smoothly converted to tellurophenes with telluride salts in high yield via a series of cascade reactions through reductive debromination, hydrotelluration, nucleophilic cyclization, and aromatization. Close inspection of the results clearly showed that the reactivity of in situ prepared telluride salts are significantly influenced by the polarity of the solvent system and the electronic nature of the substituent on the enyne substrate. This method reports the first direct synthesis of 3-aryltellurophenes in high yields at room temperature. This novel reaction strategy is also found to be a promising synthetic method for multisubstituted tellurophenes and selenophenes.

Regioselective Rh-Catalyzed Hydroformylation of 1,1,3-Trisubstituted Allenes Using BisDiazaPhos Ligand

The efficient hydroformylation of 1,1,3-trisubstituted allenes is accomplished with low loadings of a Rh catalyst supported by a BisDiazaPhos (BDP) ligand. The ligand identity is key to achieving high regioselectivity, while the mild reaction conditions m

Vanadium(V)-mediated rearrangement/halogenation cascade: Synthesis of α-haloenones from propargyl alcohols

A method is described for the oxidative Meyer–Schuster-type rearrangement of propargylic alcohols to (Z)-α-chloro- and α-iodoenones using VOCl3 as a multifunctional reagent. The vanadium reagent is found to serve as rearrangement promoter as well as an active chlorenium ion donor. Yields are improved when VOCl3 is employed in conjunction with N-halosuccinimide reagents, giving some insights into the complex mechanism.

Redox-Neutral Arylations of Vinyl Cation Intermediates

Herein we present a new unified concept for C?C bond formation under redox-neutral conditions. Our strategy hinges upon interception of a vinyl cation with a sulfoxide resulting in simultaneous C–C and C?O bond formation and arylation. A range of structurally diverse vinyl cations are generated in situ in the presence of a sulfoxide, resulting in hydrative arylation, direct arylation of enol triflates and interrupted Meyer–Schuster rearrangement. Mechanistic investigations showcase the crucial role played by the fleeting vinyl cation intermediate and structural features that lead to its stabilization. Applications of the reaction products to synthesis are also presented. (Figure presented.).

Cadmium(II) Chloride-Catalyzed Dehydrative C?P Coupling of Propargyl Alcohols with Diarylphosphine Oxides to Afford Allenylphosphine Oxides

The cadmium(II) chloride-catalyzed dehydrative C?P cross-coupling reaction of propargyl alcohols with diarylphosphine oxides is reported. Several propargyl alcohols including those bearing the sterically demanding tert-butyl group at the triple bond terminus can be used as good substrates in the reaction to produce the corresponding allenylphosphine oxides in good to high yields in acetonitrile at 100 °C. The reaction can also be easily scaled up to a gram-scale synthesis. A mechanism study indicates that the reaction may proceed through a process of propargylic substitution to generate phosphonite intermediates followed by [2,3] sigmatropic rearrangement to produce the allenyl products, rather than through a common allenylative substitution resulting from P-nucleophilicity. (Figure presented.).

Silver-catalyzed efficient synthesis of vinylene carbonate derivatives from carbon dioxide

It was found that the silver salt and base was an efficient catalytic system for the reaction of the secondary propargylic alcohol with carbon dioxide to afford various corresponding vinylene carbonate derivatives in good to high yields under mild conditions. Georg Thieme Verlag Stuttgart New York.

A convenient approach to β-heteroarylated (C-N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles

An efficient and direct approach to β-heteroarylated (C-N bond) ketones is demonstrated. Base promoted redox isomerization of propargyl alcohol to α,β-unsaturated ketone followed by conjugate addition to NH-heteroarenes affords a wide range of β-heteroarylated ketones in good to excellent yields. Aryl, heteroaryl, alkyl C(sp), and terminal alkynes containing unactivated propargyl alcohols effectively undergo redox-isomerization conjugate addition (RICA) with NH-heteroarenes. Reaction of 3-substituted pyrazoles or indazole with propargyl alcohols enables highly regioselective products. A diverse range of NH-bearing nucleophiles such as: pyrazoles, imidazole, triazoles, pyrrole, indoles and aniline participate in this reaction and deliver the corresponding β-heteroarylated ketones.

A concise access to (polyfluoroaryl)allenes by Cu-catalyzed direct coupling with propargyl phosphates

A copper-based catalyst system for the direct coupling of polyfluoroarenes with propargyl phosphates has been developed. The catalysis can provide a rapid and concise access to (polyfluoroaryl)allenes, which can be important building blocks for the synthesis of fluorinated functional materials.

Enantioselective alkynylation of aldehydes with 1-haloalkynes catalyzed by tethered bis(8-quinolinato) chromium complex

The first example of Cr-catalyzed asymmetric alkynylation of aldehydes with 1-iodo- and 1-bromoalkynes was developed. The use of tethered bis(8-quinolinato) chromium catalyst (3 mol %) allowed preparation of enantioenriched propargyl alcohols with good yields and enantioselectivities up to 92% ee. 1-Bromoalkynes can be activated by the introduction of a cobalt porphine cocatalyst, which enables shorter reaction times without any loss of enantiocontrol.