27944-90-7

Upstream product

• 931-49-7 1-ethenylcyclohexene 
• 28075-50-5 cyclohex-1-en-1-yl trifluoromethane sulfonate 
• 922-67-8 propynoic acid methyl ester 
• 67-56-1 methanol 
• 71-43-2 benzene 
• 79-22-1 methyl chloroformate 
• 201230-82-2 carbon monoxide 
• 27944-89-4 3-(cyclohex-1-en-1-yl)propiolic acid 

Downstream Products

• 94002-02-5 3--3-phenoxy-acrylsaeure 
• 1239476-40-4 C₂₁H₃₆O₆Si 
• 1239476-36-8 C₂₁H₃₆O₆Si 
• 27944-89-4 3-(cyclohex-1-en-1-yl)propiolic acid 
• 1397284-81-9 C₂₀H₂₁NO₃ 
• 1379617-92-1 methyl 6-cyclohexenyl-3-methyl-1,4-diphenyl-4H-cyclopenta[c]furan-5-carboxylate 
• 107644-69-9 methyl (Z)-3-(1-cyclohexen-1-yl)-2-propenoate 
• 93015-56-6 3--3-phenoxy-acrylsaeure-methylester 

Relevant academic research and scientific papers

Alkynylboration Reaction Leading to Boron-Containing π-Extended cis-Stilbenes as a Highly Tunable Fluorophore

An unprecedented boron-containing fluorophore, π-extended cis-stilbene, obtained via alkynylboration reaction of alkynamide is reported. Boron-containing π-extended cis-stilbenes emit fluorescence with high quantum yields in the solid state and exhibit aggregation-induced emission enhancement. The broad substrate scope of the alkynylboration reaction offers facile access to electronically diverse structures, enabling fine-tuning of light absorption/emission characteristics. The boron-containing π-extended cis-stilbene with a diphenylamino group displays solvatofluorochromism via an intramolecular charge-transfer transition.

Trans-Hydroboration of Propiolamides: Access to Primary and Secondary (E)-β-Borylacrylamides

A base-mediated trans-hydroboration of propiolamides that provides access to previously elusive primary and secondary (E)-β-borylacrylamide products has been developed. In the presence of n-butyllithium and pinacolborane, complete regioselectivity and ste

Transition Metal-Free Trans Hydroboration of Alkynoic Acid Derivatives: Experimental and Theoretical Studies

We report a phosphine-catalyzed trans hydroboration of alkynoate esters and amides. The reaction proceeds under mild conditions with exclusive (E)-selectivity to afford (E)-β-boryl acrylates and (E)-β-boryl acrylamides in good to excellent yields. The reaction is tolerant of a variety of functional groups and allows efficient access to novel oxaboroles as well as a pargyline derivative (MAO inhibitor). Theoretical calculations suggest an internal hydride generates a phosphonium allenoxyborane followed by the formation of a key phosphonocyclobutene intermediate that collapses in a stereoselective, rate-limiting step.

Palladium-Catalyzed Synthesis of Conjugated Allenynes via Decarboxylative Coupling

A new strategy to access conjugated allenynes via a decarboxylative coupling of propargyl esters of propiolates has been developed. In this process, allenyl-palladium intermediates are coupled with acetylides that are generated in situ to form the conjuga

Iridium-catalyzed [2+2+2] cycloaddition of α,ω-diynes with alkynyl ketones and alkynyl esters

We found that the combination of [Ir(cod)Cl]2 and rac-BINAP served as an efficient catalyst for the [2+2+2] cycloaddition of 2,7-nonadiyne derivatives and related compounds with alkynyl ketones and alkynyl esters. The corresponding products wer

Cationic rhodium(I)-catalyzed regioselective tandem heterocyclization/[3+2] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with alkynes

RhI in two minds: A RhI-catalyzed tandem heterocyclization/[3+2] cycloaddition reaction was developed that provides rapid, efficient, and stereoselective access to highly substituted cyclopenta[c]furans from readily available 2-(1-alkynyl)-2-alken-1-ones and alkynes (see scheme). The cationic RhI acts as both a Lewis acid and a conventional transition-metal catalyst, providing the first example of a RhI species acting as a Lewis acid. Copyright

Highly satisfactory alkynylation of alkenyl halides via Pd-catalyzed cross-coupling with alkynylzincs and its critical comparison with the sonogashira alkynylation

(Matrix presented) The Pd-catalyzed alkynylation of various alkenyl halides and triflates with alkynylzincs proceeds well even with alkynyl derivatives containing electron-withdrawing groups. The reaction appears to be highly general. Noteworthy is that the corresponding Sonogashira reactions under various reported conditions are significantly less satisfactory in all cases performed in this study.

On the Regioselectivity and Stereoselectivity of the Carbene Transfer from Fischer Carbene Complexes to Trisubstituted Electron-Deficient 1,3-Dienes

Thermal reactions of Fischer carbene complex 1 with trisubstituted electron-deficient 1,3-dienes 7, 8, 23, 25, 32, and 35 provided highly substituted vinylcyclopropanes in good yields.The carbene transfer proceeds highly regioselectively favouring cyclopropanation of the double bond not bearing the ester function.In addition, the diastereoselectivity is generally fairly high in preference of cyclopropanes with the methoxy group cis-positioned with respect to the olefin moiety.The reaction of methylcarbene complex 2 with diene ester 8 displays inversed regioselectivity.These ovservations are discussed together with solvent effects, and a mechanistic rationale is presented. - Key Words: Chromium complexes/ Carbene complexes/ 1,3-Dienes, electron-deficient/ Cycloadditions/ Vinylcyclopropanes, donor-acceptor-substituted/ Diastereoselectivity/ Regioselectivity

Efficient preparative-scale procedures for the Pd-catalyzed methoxycarbonylation of acetylenes

A number of acetylenic esters RC≡C-COOCH3 have been prepared in good yields on a preparative scale by Pd-catalyzed methoxycarbonylation of acetylenes RC≡CH.