39517-83-4

Upstream product

• 66090-05-9 2-methyl-4-methylene-2-phenyl-[1,3]dioxolane 
• 128496-99-1 2-Phenyl-4-<(phenylsulfonyl)methyl>furan 
• 118668-63-6 3-[(2-bromo-1-methoxy-1-phenyl)-ethoxy]-propyne 
• 89880-33-1 3-Hydroxy-3-methyl-1-phenyl-4-(tetrahydro-pyran-2-yloxy)-butan-1-one 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 39517-87-8 2-methyl-4-phenyl-but-3-yne-1,2-diol 
• 7664-93-9 sulfuric acid 
• 945983-25-5 C₁₇H₁₄O₂S 
• 4747-13-1 α-methoxystyrene 
• 536-74-3 phenylacetylene 
• 93-91-4 1-phenylbutan-1,3-dione 
• 128497-05-2 (Z)-4-Benzenesulfonyl-3-bromomethyl-1-phenyl-but-3-en-1-one 
• 57951-69-6 2-methylene-4-phenylbut-3-yn-1-ol 

Downstream Products

• 106595-40-8 (+/-)(1Ξ,2Ξ)-5-methyl-1-phenyl-7-oxa-norborn-5-ene-2r,3c-dicarboxylic acid-anhydride 

Relevant academic research and scientific papers

Chemo-Enzymatic Metathesis/Aromatization Cascades for the Synthesis of Furans: Disclosing the Aromatizing Activity of Laccase/TEMPO in Oxygen-Containing Heterocycles

The unprecedented Trametes versicolor laccase/TEMPO-catalyzed aromatization of 2,5-dihydrofurans to furans is described. A variety of furan derivatives have been synthesized in moderate to high conversions (21-99%) and yields (20-76%) under mild reaction

A biosynthetically inspired route to substituted furans using the Appel reaction: Total synthesis of the furan fatty acid F5

Appel reaction conditions have been harnessed to affect a mild biosynthetically inspired dehydration of endoperoxides to deliver multi-substituted electron rich furans. Unlike traditional dehydrative procedures, this method is metal and acid free, and can be achieved under redox neutral conditions. It is general for a range of aryl and alkyl substituted endoperoxides, and is functional group tolerant. Furthermore, this procedure has been used to deliver an effective total synthesis of the furan fatty acid (FFA) F5.

The Power of Ferrocene, Mesoionic Carbenes, and Gold: Redox-Switchable Catalysis

Catalysis with gold(I) complexes is a useful route for synthesizing a variety of important heterocycles. Often, silver(I) additives are necessary to increase the Lewis acidity at the gold(I) center and to make them catalytically active. We present here a

Asymmetric hydrogenation of furans and benzofurans with iridium-pyridine-phosphinite catalysts

Enantioselective hydrogenation of furans and benzofurans remains a challenging task. We report the hydrogenation of 2- and 3-substituted furans by using iridium catalysts that bear bicyclic pyridine-phosphinite ligands. Excellent enantioselectivities and high conversions were obtained for monosubstituted furans with a 3-alkyl or 3-aryl group. Furans substituted at the 2-position and 2,4-disubstituted furans proved to be more difficult substrates. The best results (80-97% conversion, 65-82% enantiomeric excess) were obtained with monosubstituted 2-alkylfurans and 2-[4-(trifluoromethyl)phenyl]furan. Benzofurans with an alkyl substituent at the 2- or 3-position also gave high conversions and enantioselectivity, whereas 2-aryl derivatives showed essentially no reactivity. The asymmetric hydrogenation of a 3-methylbenzofuran derivative was used as a key step in the formal total synthesis of the cytotoxic naphthoquinone natural product (-)-thespesone.

Poly(ethylene glycol) as a reaction matrix in platinum- or gold-catalyzed cycloisomerization: A mechanistic investigation

Design for diversity: A new catalytic system based on PEG-3400 and a metal salt (Pt or Au) was designed to efficiently perform a cycloisomerization reaction under microwave irradiation, which gave diverse heterocycles in good to excellent yields, after a

Cyclization of 2-alkynylallyl alcohols to highly substituted furans by gold(I)-carbene complexes

Various 2-alkynylallyl alcohols were synthesized by a generally applicable Sonogashira coupling protocol. Subsequent gold-catalyzed transformation was investigated. The use of AuI catalysts bearing carbene ligands, of either the N-heterocyclic carbene or nitrogen acyclic carbene type, delivered the desired products with low catalyst loadings and under very mild reaction conditions. A broad array of substrates was tested, including alkyl-, alkenyl-, and aryl-substituted alkynes, as well as substrates with two alkynyl moieties. The methodology turned out to have a broad scope. Secondary allyl alcohols were also tolerated, and the resulting trisubstituted furans could be isolated in high yields. Easily accessible 2-alkynylallyl alcohols were transformed into highly substituted furans under very mild reaction conditions by the use of gold(I)-carbene catalysts. A broad range of substrates could be transformed in high yields and within short reaction times.

A short synthesis of highly substituted furans from alkenyl aryl ketones with dichloromethyl phenyl sulfoxide

Two-step synthesis of 2-aryl-5-(phenylsulfanyl)furans was achieved starting from alkenyl aryl ketones and dichloromethyl phenyl sulfoxide. The phenylsulfanyl group was successfully converted to other functional groups, via sulfinyl group, to give highly substituted 2-arylfurans in good overall yields.

Catalytic regioselectivity control in ring-opening cycloisomerization of methylene- or alkylidenecyclopropyl ketones

2-Methylene- or alkylidenecyclopropanyl ketones were easily prepared by the regioselective cyclopropanation of allenes or the reaction of methylene-/alkylidenecyclopropanyllithium with N,N-dimethyl carboxylic acid amides. Due to the presence of the exo-cy

Synthesis of 2,4-disubstituted furans and 4,6-diaryl-substituted 2,3-benzo-1,3a,6a-triazapentalenes

Reactions of acylacetylenes 1a-h with benzotriazole 2 give intermediates 3a-h. The treatment of 3a-h with trimethylsulfonium iodide in the presence of base give intermediate oxiranes 4a-h and 2,3-benzo-1,3a,6a-triazapentalenes 7d-g depending on substituent. Acid-catalyzed rearrangement of crude 4a-h give 2,4-disubstituted furans 5a-h.

Tuning the regioselectivity in the palladium(II)-catalyzed isomerization of alkylidene cyclopropyl ketones: A dramatic salt effect

Useful building blocks are formed in this [PdCl2(CH3CN)2]-catalyzed regioselective isomerization reaction of alkylidene cyclopropyl ketones, in which a dramatic salt effect was observed. In the presence of Nal, the reactio