50401-30-4

Upstream product

• 329200-88-6 N-(but-2-en-1-yl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 
• 50401-85-9 (E)-N-(but-2-en-1-yl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 303767-26-2 3-allyl-5-vinyloxazolidin-2-one 
• 120568-74-3 N-allyl-N-(2-hydroxy-3-butenyl)amine 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 121224-83-7 N-(E)-4-iodo-2-butenyl-N-propargyl-p-toluenesulfonamide 
• 121224-78-0 N-allyl-N-(4-iodo-2-butenyl)-4-methylbenzenesulfonamide 
• 153391-78-7 (Z)-N-{4-[(methoxycarbonyl)oxy]but-2-enyl}-N-(prop-2-enyl)-p-toluenesulfonamide 
• 121224-71-3 Acetic acid (E)-4-[allyl-(toluene-4-sulfonyl)-amino]-but-2-enyl ester 
• 120568-65-2 Acetic acid (E)-4-[allyl-(toluene-4-sulfonyl)-amino]-but-2-enyl ester 
• 120568-67-4 1-(N-allyl-N-p-toluenesulfonylamino)-2-hydroxy-3-butene 

Relevant academic research and scientific papers

Photochemical and radical initiator-induced reaction of allylic indium compounds

Intramolecular cyclization of allylic radicals generated from allylindium compounds both by photolysis or by the reaction of radical initiators was examined. The photolysis of allylic indium compounds, prepared from 8-bromo- or 8-iodooct-1,6-dienes and powdered indium metal, led to the formation of the 5-exo-trig products. Benzoyl peroxide as a radical initiator was also effective for the cyclization. In contrast, the radical initiators with oxidizing nature, such as tert-butyl hypochlorite, induced iodocyclization producing iodomethylcyclopentane via an oxidation of the iodide on the indium atom.

Inter/Intramolecular Cascade of 1,6-Enynes Catalyzed by All-Metal Aromatic Tripalladium Complexes and Carboxylic Acids

Trinuclear all-metal aromatic clusters are an original class of molecules with a cyclic and planar metal core. Characterized by peculiar metal-metal delocalized bonds, they represent a new frontier in transition-metal catalysis. We report a study on C-C-forming reactions of polyunsaturated substrates catalyzed by trinuclear all-metal aromatic palladium clusters. The synthesis of two new families of tricyclic compounds was obtained with a broad functional group tolerance under mild reaction conditions. A peculiar regio- and diastereoselectivity characterized the method, demonstrating that trinuclear palladium complexes are complementary to their popular mononuclear peers. Furthermore, preliminary studies on the mechanism of these polycyclization reactions revealed unique features of the homogeneous catalytic system.

Enantioselective rhodium-catalyzed cycloisomerization of (E)-1,6-enynes

An enantioselective rhodium(I)-catalyzed cycloisomerization reaction of challenging (E)-1,6-enynes is reported. This novel process enables (E)-1,6-enynes with a wide range of functionalities, including nitrogen-, oxygen-, and carbon-tethered (E)-1,6-enynes, to undergo cycloisomerization with excellent enantioselectivity, in a high-yielding and operationally simple manner. Moreover, this RhI-diphosphane catalytic system also exhibited superior reactivity and enantioselectivity for (Z)-1,6-enynes. A rationale for the striking reactivity difference between (E)- and (Z)-1,6-enynes using RhI-BINAP and RhI-TangPhos is outlined using DFT studies to provide the necessary insight for the design of new catalyst systems and the application to synthesis. A solution after 15 years: The first rhodium(I)-catalyzed asymmetric cycloisomerization reaction of challenging (E)-configured 1,6-enyes is reported. The reaction provides access to five-membered carbo- and heterocycles with excellent enantioselectivity. DFT studies provide a rationale for the striking reactivity difference between (E)- and (Z)-1,6-enynes using RhI-BINAP and RhI-TangPhos.

Manganese porphyrin catalyzed cycloisomerization of enynes

Cycloisomerization of 1,6-enynes to five- or six-membered ring systems is successfully carried out in the presence of a cationic manganese(III) catalyst. The use of a structurally rigid tetradentate porphyrin as the equatorial ligand and a weakly coordina

A cheap metal for a "noble" task: Preparative and mechanistic aspects of cycloisomerization and cycloaddition reactions catalyzed by low-valent iron complexes

Reaction of ferrocene with lithium in the presence of either ethylene or COD allows the Fe(0)-ate complexes 1 and 4 to be prepared on a large scale, which turned out to be excellent catalysts for a variety of Alder-ene, [4+2], [5+2], and [2+2+2] cycloaddi

Radical reactions initiated by the photochemical cleavage of carbon-indium bonds of organoindium compounds

Intra- and intermolecular reactions of carbon-centered radicals generated by photolysis of organoindium compounds were examined. The photolysis of vinylindium compounds and indium acetylides provided vinyl and alkynyl radicals, respectively, which were trapped with ethyl iodoacetate giving the corresponding β,γ-unsaturated esters. Allylic indium compounds, prepared from 8-bromo- or 8-iodooct-1,6-dienes and powdered indium metal, underwent an intramolecular radical cyclization to afford the 5-exo-trig product.

New indium-mediated cyclisation reactions of tethered haloenynes in aqueous solvent systems

The intramolecular cyclisation of tethered allyl bromides onto terminal alkynes mediated by metallic indium proceeds smoothly and cleanly in mixtures of THF and H2O to give unsaturated carbocycles and heterocycles in good yield. Alternatively, the cyclisation may be carried out in anhydrous THF with the aid of acid catalysis. The reaction is also mediated by a range of indium salts and proceeds with substoichiometric quantities of indium in the presence of a co-reductant. Deuteration studies show that the reaction proceeds via a concerted syn carboindination of the carbon-carbon triple bond to give an intermediate, which is protonated in situ.

Cyclization of 1-bromo-2,7- and 1-bromo-2,8-enynes mediated by indium

(Chemical Equation Presented) The cyclization of 1-bromo-2,7- and 1-bromo-2,8-enynes mediated by indium in DMF produced five- and six-membered cyclic compounds. Although KI was a necessary additive in the cyclization of terminal 1-bromo-2,7-enynes to give the desired products at 25°C, reactions of terminal 1-bromo-2,8-enynes and internal 1-bromo-2,7-enynes with indium proceeded at 100°C in DMF without KI. After cyclizations, subsequent cross-coupling reaction and iodolysis increase the usefulness of this reaction.

Efficient Metallo-Ene Reactions in Organoaqueous Phase

(matrixpresented)The easily prepared catalyst systems PdCl2, RhCl2 (COD) 2, NiCl2·6H2O, or Ni (COD) 2/TPPTS have been found to form a C-C bond in organoaqueous medium. Intramolecular metall

Studies towards asymmetric catalyzed metallo-ene reactions

The asymmetric catalyzed metallo-ene reaction was studied. Enantioselectivities up to 47% were observed using the Pd-ene reaction applied on the substrate 4.