70672-97-8

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 106-96-7 propargyl bromide 
• 865350-17-0 4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane 
• 100-52-7 benzaldehyde 
• 14371-10-9 (E)-3-phenylpropenal 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 14657-22-8 allenyltrimethylsilane 
• 13361-64-3 trimethyl(propargyl)silane 

Downstream Products

• 55629-83-9 (3E)-1-methoxy-4-phenyl-3-buten-2-one 
• 107487-40-1 (E)-4-methoxy-1,4-diphenylbut-2-en-1-one 
• 1398116-92-1 C₁₁H₁₁⁽²⁾HO 
• 1398116-82-9 C₁₁H₁₁⁽²⁾HO₂ 
• 1398116-90-9 5-methoxy-1,5-diphenylpent-2-yn-1-one 

Relevant academic research and scientific papers

Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates

Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN3-Et3N·HCl results in the formation of azidotetrazoles. Under microwave irradiation, successive fragmentation of the azidotetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous alkynes. Treatment of ketone-derived CPs with TMSN3 and Bu2SnO as catalyst in toluene at reflux directly yields the corresponding internal alkynes, whereas the reaction of aldehyde-derived CPs with NaN3-Et3N·HCl in THF at reflux or TMSN3-Bu2SnO (cat.) in toluene at reflux provides homologous terminal alkynes in good yields. These reactions take place under neutral conditions and can be successfully extended to obtain alkynes that are not usually accessible from the corresponding carbonyl compounds by the Ohira-Bestmann or Shioiri procedures, which require basic conditions.

Gold-catalyzed oxidative rearrangement of homopropargylic ether via oxonium ylide

Synthetically useful α,β-unsaturated carbonyl compounds were obtained from gold-catalyzed oxidative rearrangement of homopropargylic ether under mild reaction conditions. Gold carbenoid and oxonium ylide are proposed as key intermediates.

Unusual carbon-carbon bond formations between allylboronates and acetals or ketals catalyzed by a peculiar indium(I) lewis acid

InIOTf has been uncovered as an effective Lewis acid catalyst for unprecedented nucleophilic substitution of acetals or ketals with allylboronates. A transmetalative SN1 mechanism is proposed in which a single InI center acts as a dual catalyst to activate both reagents sequentially. Contrary to the classic γ-selectivity of allylsilanes (Hosomi-Sakurai reaction), this InI-catalyzed borono variant displays distinct α-selectivity. Substrate scope and functional group tolerance proved to be excellent.

Lewis acid-catalyzed three-component condensation reactions of aldehydes, alkoxysilanes, and allenylsilanes: Synthesis of α-propargyl ethers

Lewis acid-catalyzed reaction of acetals with allenylsilanes and the three-component reactions of aldehydes, alkoxysilanes, and allenylsilanes are described. Both reactions are strongly dependent on the substituent at the α-position of allenylsilanes. Allenylsilanes having bulky substituents such as the tert-butyl and isopropyl groups result in the corresponding α-propargyl ethers in high yields, whereas allenylsilanes having the methyl and ethyl groups afford not only the corresponding α-propargyl ethers in low yield but also cyclopropyl ketones and α,β-unsaturated ketones as by-products.

Lewis acid-catalyzed three-component condensation reactions of aldehydes, alkoxysilanes, and propargylsilane: Synthesis of α-allenyl ethers

For simultaneous construction of a polyether backbone and the allenyl side chains, Lewis acid-catalyzed three-component condensation reactions of aldehydes, alkoxytrimethylsilanes, and 1-trimethylsilyl-2-butyne were studied. The reaction of these three compounds took place in the presence of a catalytic amount of TrClO4 at -78°C to yield the corresponding α-allenyl ethers in good yields. This reaction was also applied to the synthesis of a polyether having allenyl side chains.