165335-53-5

Upstream product

• 100-52-7 benzaldehyde 
• 1794-48-5 1-bromo-3-phenylprop-2-yne 
• 37559-19-6 3-(phenyl)prop-2-yn-1-yl benzoate 
• 82490-61-7 3-phenyl-2-propyn-1-yl methanesulfonate 
• 459126-04-6 diethyl (3-phenylprop-2-yn-1-yl) phosphate 
• 536-74-3 phenylacetylene 
• 1425747-00-7 4,4,5,5-tetramethyl-2-(3-phenylprop-2-yn-1-yl)-1,3,2-dioxaborolane 
• 73513-15-2 (3-iodo-1-propyn-1-yl)benzene 
• 591-50-4 iodobenzene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 420121-38-6 methyl (3-phenylprop-2-yn-1-yl) carbonate 

Downstream Products

• 1198184-42-7 C₁₉H₁₆O 
• 1722-69-6 3,4-diphenylbut-3-en-2-one 
• 38661-88-0 (E)-1,2-diphenylbut-1-en-3-one 
• 1422370-80-6 3-pentyl-4,5-diphenyl-2(5H)-furanone 
• 1399842-90-0 (E)-but-1-en-3-yne-1,2-diyldibenzene 

Relevant academic research and scientific papers

Iron-Catalyzed Tertiary Alkylation of Terminal Alkynes with 1,3-Diesters via a Functionalized Alkyl Radical

Direct oxidative C(sp)?H/C(sp3)?H cross-coupling offers an ideal and environmentally benign protocol for C(sp)?C(sp3) bond formations. As such, reactivity and site-selectivity with respect to C(sp3)?H bond cleavage have remained a persistent challenge. Herein is reported a simple method for iron-catalyzed/silver-mediated tertiary alkylation of terminal alkynes with readily available and versatile 1,3-dicarbonyl compounds. The reaction is suitable for an array of substrates and proceeds in a highly selective manner even employing alkanes containing other tertiary, benzylic, and C(sp3)?H bonds alpha to heteroatoms. Elaboration of the products enables the synthesis of a series of versatile building blocks. Control experiments implicate the in situ generation of a tertiary carbon-centered radical species.

Catalytic Reductive Cross-Coupling between Aromatic Aldehydes and Arylnitriles

A reductive cross-coupling reaction between aromatic aldehydes and arylnitriles using a copper catalyst and a silylboronate as a reductant is reported. This protocol represents an unprecedented approach to the chemoselective synthesis of α-hydroxy ketones by electrophile–electrophile cross-coupling.

An efficient Nozaki-Hiyama allenylation promoted by the acid derived MIL-101 MOF

A concise synthesis of the sulfonic acid-containing MIL-101 MOF catalyst was reported using commercially available materials. A series of characterization of as-synthesized MIL-101-SO3H including SEM, XRD, FTIR, BET and TGA was also demonstrated. Using MIL-101-SO3H as a catalyst, an efficient Nozaki-Hiyama allenylation reaction was achieved to generate various polyfunctionalized α-allenic alcohols in high yield and good selectivity. Taking advantage of the high acidity of the MIL-101-SO3H MOF structure, such transformations were also achieved under mild reaction conditions and short reaction times. Based on our observed evidence during this study, a mechanism was proposed involving a substrate activation/γ-nucleophilic addition reaction sequence. In addition, the MIL-101-SO3H catalyst can be recycled ten times during the Nozaki-Hiyama allenylation reaction without compromising the yield and selectivity.

Acid-catalyzed synthesis of α,β-disubstituted conjugated enones by a Meyer-Schuster-type rearrangement in allenols

A novel, direct and simple methodology to gain access to α,β-disubstituted conjugated enones from α-allenols in a sustainable metal catalysis context, considering the inexpensiveness and environmentally friendliness of iron(III) species and protons, has b

Theoretical support for the involvement of a radical pathway in the formation of allenylzincs from propargyl iodides and dialkylzincs: Influence of zinc coordination

Propargyl iodides are good precursors for allenylzincs via reaction with diethylzinc, even in nondegassed medium. These reactions proceed via zinc/iodine exchange. Owing to the previously reported detection of propargyl radical by ESR experiments, in this process a radical mechanism was suspected. Calculations of the C-Zn BDEs in allenyl- and propargylzinc species were performed with the CBS-QB3 method to demonstrate that propargyl radicals could undergo homolytic substitution at zinc. The stabilization of allenylzinc derivatives by chelation, made possible by the selection of appropriate ortho-substituted 3-phenylalkynyl iodides as precursors, was shown to influence the regioselectivity of their addition to aldehydes and ketones. The more stabilized the chelated allenylzinc intermediate, the higher the ratio of homopropargylic alcohols.

Nickel-catalyzed indium(I)-mediated syn-selective propargylation of aldehydes

Low-valent indium(I)-mediated nickel-catalyzed propargylation of aldehydes is described. The nickel/indium(I)-mediated reaction of propargylic carbonates possessing different substitution patterns afforded syn-homopropargylic alcohols in high yields upon coupling with a variety of carbonyl compounds. Both the nickel catalyst and the phosphane ligands were found to play a crucial role in this transformation. The diastereoselectivity is strongly dependent on the ligand employed. A mechanism involving umpolung of the propargylnickel intermediates under the influence of low-valent indium is proposed to account for the dependence of the stereochemical characteristics of the phosphane ligands.

Nickel-catalyzed indium(I)-mediated syn-selective propargylation of aldehydes

Low-valent indium(I)-mediated nickel-catalyzed propargylation of aldehydes is described. The nickel/indium(I)-mediated reaction of propargylic carbonates possessing different substitution patterns afforded syn-homopropargylic alcohols in high yields upon coupling with a variety of carbonyl compounds. Both the nickel catalyst and the phosphane ligands were found to play a crucial role in this transformation. The diastereoselectivity is strongly dependent on the ligand employed. A mechanism involving umpolung of the propargylnickel intermediates under the influence of low-valent indium is proposed to account for the dependence of the stereochemical characteristics of the phosphane ligands.

Direct allenol-based stereocontrolled access to substituted (E)-1,3-enynes

A stereoselective synthesis of 1-substituted (E)-2-aryl-but-1-en-3-ynes, including tetrasubstituted alkenes, has been developed from aryl-substituted α-allenols by treatment with the AcCl-NaOH (aqueous) system. This transformation might be explained throu

Regioselective addition reactions of propargyl bromides to carbonyl compounds with gallium catalyzed by indium

Reactions of organogallium reagents generated from propargyl bromides having substituents at the γ-position and gallium in the presence of 5 mol % of indium with aldehydes and ketones selectively produced homoallenyl alcohols in good to excellent yields.

Indium-mediated propargylation of aldehydes: Regioselectivity and enantioselectivity studies

An enantioselective propargylation reaction of aldehydes with enantioselectivity up to 85% has been achieved in organic solvents by using stoichiometric amounts of (-)-cinchonidine as the chiral source.