14174-48-2

Upstream product

• 60444-22-6 3,4-Dichloro-1-cyclohexyl-butan-1-one 
• 107-05-1 3-chloroprop-1-ene 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 10160-87-9 Propiolaldehyde diethyl acetal 
• 2043-61-0 cyclohexanecarbaldehyde 
• 584-12-3 2-bromofuran 
• 931-51-1 cyclohexylmagnesiumchloride 
• 1338347-52-6 C₁₆H₂₆O₃ 
• 1338347-15-1 4-(1-methoxycyclohexyl)but-3-yn-1-ol 
• 626-62-0 Cyclohexyl iodide 

Relevant academic research and scientific papers

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.

Synthesis of 2-substituted furans by iron- and palladium-catalyzed coupling reactions

The synthesis of 2-substituted furans via palladium- and iron-catalyzed coupling utilizing 2-bromofuran is described. Whereas palladium-catalyzed Suzuki coupling effectively provided the corresponding aryl furans, little or no product was obtained by palladium-catalyzed coupling with various alkyl nucleophiles. Iron-catalyzed coupling proved effective for the synthesis of primary and secondary alkyl furans in modest yields and aryl furans in low yields. Georg Thieme Verlag Stuttgart New York.

Generation of α,β-unsaturated platinum carbenes from homopropargylic alcohols: Rearrangements to polysubstituted furans

A number of diversely substituted furans are synthesized via a cycloisomerization process that goes through a unique metal carbene species. Both ligand structure and the nature of the leaving group are evaluated. The characteristics of the carbene intermediate can be modulated, resulting in highly selective hydrogen or silicon group migrations.

Efficient one-pot synthesis of 2-substituted furans from 3,3-diethoxypropyne and aldehydes using a Ti(O-i-Pr)4/2i-PrMgCl reagent

A new, efficient and direct synthetic method for synthesizing 2-substituted furans using titanium-alkyne complex from easily preparable lithium propargyl alcohol derivatives derived from commercially available 3,3-diethoxypropyne, n-butyllithium and aldehydes by a Ti(O-i-Pr)4/2 i-PrMgCl reagent in 68-85percent yields.

HETEROCYCLIZATION OF β,γ-DICHLORO KETONES AS A METHOD FOR THE SYNTHESIS OF FURAN DERIVATIVES

Dichloro ketones obtained from acyl chlorides and allyl or β-methylallyl chloride undergo spontaneous cyclization to give 2-alkyl- and 2,4-dialkylfurans when they are heated; the intermediates in the case of 2,3-dichloropropene split out a molecule of hydrogen chloride to give 3,4-dichloro-2-butenones.