71725-42-3

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 609-39-2 2-nitrofuran 
• 109-72-8 n-butyllithium 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 693-02-7 hex-1-yne 
• 542-69-8 1-iodo-butane 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 2966-50-9 silver trifluoroacetate 

Downstream Products

• 117266-79-2 4-cyano-5-phenyl-1H-pyrrole-2,3-dione 
• 117290-47-8 2,5-cyano-1,6-diimino-1,6-diphenyl-hexane-3,4-dione 
• 1068579-57-6 ((3-butylfuran-2-yl)oxy)triisopropylsilane 

Relevant academic research and scientific papers

A new regioselective synthesis of 3-substituted furan-2(5H)-ones by palladium-catalysed reductive carbonylation of alk-1-ynes

3-Alkyl- or 3-aryl-substituted furan-2(5H)-ones are obtained directly in fair yields by reductive carbonylation of alk-1-ynes in the presence of catalytic amounts of palladium iodide in conjunction with potassium iodide (10 eq.) and water (200 eq.). Simultaneous oxidation of CO to CO2 accounts for the stoichiometry of the process. Reactions are carried out in dioxane under mild conditions (80 °C and 10 atm of carbon monoxide).

Combined oxidative and reductive carbonylation of terminal alkynes with palladium iodide-thiourea catalysts

Oxidative carbonylation of alkynes can be carried out catalytically in the absence of added oxidants if it is coupled with a reductive carbonylation process at the expense of the same alkyne involved in the oxidative process.Maleic esters (from oxidative carbonylation) and unsaturated lactones (from reductive carbonylation) are the main products formed under the catalytic action of palladium iodide complexes with thiourea (tu).A complex, formally corresponding to the ionic formula I, allows the reaction of alkylacetylenes at room temperature and atmospheric pressure.With activated alkynes such as phenylacetylene, or with alkynes containing coordinating groups, other palladium complexes with two or four molecules of thiourea are also active, although to a lesser extent.Identification of the organic by-products gives a hint of the mechanism by which coupling of oxidative and reductive carbonylation occurs.Keywords: Palladium; Alkynes; Oxidative carbonylation; Reductive carbonylation; Catalysis, Thiourea

Nitrodienic-like Reactivity of 2-Nitrofuran with Organometallic Reagents: One-step Synthesis of Alkylfuranones

2-Nitrofuran reacts with Grignard, alkyllithium, dialkylcadmium and heterocuprate reagents affording mixtures of 5-alkyl- and 3-alkyl-2-furanones.

Synthesis of cis and trans Whisky and Cognac Lactones by the Regiocontrolled Alkylation of 2-(Trimethylsiloxy)furan

The racemic cis- and trans-5-butyltetrahydro-4-methylfuran-2-ones ( = whisky lactones) and their higher homologues tetrahydro-4-methyl-5-pentylfuran-2-ones ( = cognac lactones) have been prepared in 2-3 steps from 2(trimethylsiloxy)furan.Regioselective alkylation of the latter afforded the 5-butyl- and 5-pentylfuran-2(5H)-ones which served as precursors for the stereocontrolled construction of either diastereoisomer of the beverage lactones.The structure and tautomerization of the diazomethane adducts of these 5-alkylfuran-2(5H)-ones are also described.

ALKYLFURANONES FROM 2-NITROFURAN: A PROMISING SYNTHETIC APPROACH

Mixtures of 5- and 3-alkyl-2-furanones are obtained from 2-nitrofuran and Grignard reagents.