121598-69-4

Upstream product

• 106-96-7 propargyl bromide 
• 105-07-7 4-cyanobenzaldehyde 
• 18295-60-8 allenylmagnesium bromide 
• 865350-17-0 4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane 
• 624-65-7 2-propynyl chloride 

Downstream Products

• 1398116-86-3 4-(1-methoxybut-3-yn-1-yl)benzonitrile 
• 71787-53-6 1-(p-cyanophenyl)-3-buten-1-ol 
• 1380114-55-5 C₁₁H₇NO 
• 574001-77-7 4-[(3-hydroxynaphthalen-2-yl)carbonyl]benzonitrile 
• 229333-41-9 4-buta-2,3-dienoylbenzonitrile 

Relevant academic research and scientific papers

Palladium(0) catalyzed regioselective carbonyl propargylation across tetragonal tin(II) oxide via redox transmetallation

Facile homopropargylation of aldehydes by propargyl bromides over tetragonal tin(II)oxide and catalytic palladium(0) occurs which is proposed to involve the prior formation of dinuclear allenylpalladium followed by redox transmetallation to β-SnO.

One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping

A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.

Stereodivergent Palladium- And Rhodium-Catalyzed Intramolecular Addition of Tosylureas to Allenes: Diastereoselective Synthesis of Tetrahydropyrimidinones

The intramolecular addition of tosylureas to allenes is highly syn-/anti-diastereoselective when employing a palladium or rhodium-based catalytic system and affords 1,3-cyclic ureas. Under palladium catalysis a range of thermodynamic anti-tetrahydropyrimi

Intramolecular Diels-Alder reactions of 1,2,4-triazines. Synthesis of 3-alkylpyridines via Raney nickel desulfurization of thieno[2,3-b]pyridines

2-Aryl-2,3-dihydrothieno[2,3-b]pyridines have been prepared via intramolecular Diels-Alder reactions of suitably 3-substituted 1,2,4-triazine intermediates, followed by their reductive desulfurization with Raney Nickel to form 3-substituted pyridines. A o

Formal metal-free γ-arylation of 1,3-dicarbonyl compounds: Via an isomerisation/1,4-addition/[3,3]-sigmatropic rearrangement sequence

A metal-free redox arylation of alkynes with sulfoxides has been developed to provide unconventional access to diverse γ-arylated 1,3-dicarbonyl compounds in an atom-economical manner. Mechanistic studies suggest that a conjugated allenone intermediate was generated in situ, which solves the problem of reactivity and regioselectivity of unsymmetrical dialkyl-substituted internal alkynes and enables the functionalisation of a broad range of substrates bearing electron-withdrawing functional groups. The resulting arylated 1,3-dicarbonyl compounds are versatile and useful building blocks for further functionalisation. This journal is

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

The propargylation of aldehydes promoted by microwave irradiation using allenylboron compounds in a chemo- and regioselective way is described. The corresponding products were obtained in short reaction time, high yield and purity without the need of any solvent when allenylboronic acid pinacol ester was used, or using a minimal amount of acetone when potassium allenyltrifluoroborate was used.

Synthesis of 4,5-Dihydropyrazoles via Palladium-Catalyzed Cyclization Reactions of β,?3-Unsaturated Hydrazones with Aryl Iodides

A novel two-component cyclization toward the synthesis of polysubstituted 4,5-dihydropyrazoles was carried out: i.e., cyclization of β,?3-unsaturated hydrazones with aryl iodides catalyzed by Pd(0). The reaction forms new carbon-carbon bonds and carbon-ni

Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated

Regioselective propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil

The propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil, an inexpensive and readily available clay, in a chemo- and regioselective way is described. The method is simple and avoids the use of air and moisture sensitive organometallics and products were obtained in good to moderate yields.

Propargylation of aldehydes using potassium allenyltrifluoroborate

The commercially available resin Amberlyst A-31 was efficiently used to promote the propargylation of aldehydes using potassium allenyltrifluoroborate. The method is simple and fast, and the products were obtained in short reaction times in high yields and purity at room temperature in a regio- and chemoselective manner.