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• 70-55-3 toluene-4-sulfonamide 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 78388-17-7 (E)-N-(but-2-enyl)-4-methylbenzenesulfonamide 
• 106-96-7 propargyl bromide 

Relevant academic research and scientific papers

Copper-catalysed hydroamination of N-allenylsulfonamides: The key role of ancillary coordinating groups

A copper-catalysed hydroamination reaction of N-allenylsulfonamides with amines has been developed through a rational approach based on mechanistic studies. The reaction is promoted by a simple copper(I) catalyst and proceeds at room temperature with complete regioselectivity and excellent stereoselectivity towards linear (E)-N-(3-aminoprop-1-enyl)sulfonamides. Density Functional Theory (DFT) studies allow interpreting the key role of unsaturated substituents on nitrogen as ancillary coordinating moieties for the copper catalyst.

Complementary Reactivity of 1,6-Enynes with All-Metal Aromatic Trinuclear Complexes and Carboxylic Acids

The distinct reactivity of 1,6-enynes in the presence of a trinuclear metal complex activated by a carboxylic acid is presented. The triplatinum catalyst enables the cyclization of the substrate and subsequent incorporation of a nucleophile in the final product. In contrast, sequential cyclization/double bond shift occurs under analogous conditions in the presence of the corresponding tripalladium complex.

A New Approach to Non-Coordinating Anions: Lewis Acid Enhancement of Porphyrin Metal Centers in a Zwitterionic Metal-Organic Framework

We describe a new strategy to generate non-coordinating anions using zwitterionic metal-organic frameworks (MOFs). By assembly of anionic inorganic secondary building blocks (SBUs) ([In(CO2)4]-) with cationic metalloporphyrin-based organic linkers, we prepared zwitterionic MOFs in which the complete internal charge separation effectively prevents the potential binding of the counteranion to the cationic metal center. We demonstrate the enhanced Lewis acidity of MnIII- and FeIII-porphyrins in the zwitterionic MOFs in three representative electrocyclization reactions: [2 + 1] cycloisomerization of enynes, [3 + 2] cycloaddition of aziridines and alkenes, and [4 + 2] hetero-Diels-Alder cycloaddition of aldehydes with dienes. This work paves a new way to design functional MOFs for tunable chemical catalysis.

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.

(Pentamethylcyclopentadienyl)iridium dichloride dimer {[IrCp*Cl 2]2}: A novel efficient catalyst for the cycloisomerizations of homopropargylic diols and N-tethered enynes

(Pentamethylcyclopentadienyl)iridium dichloride dimer {[IrCp*Cl 2]2}-catalyzed hydroalkoxylation of bis-homopropargylic alcohols provides an efficient access to dioxabicyclo[2.2.1]ketals. The cycloisomerizations proceed under mild conditions, with low catalytic loadings and short reaction times. This new protocol involving an Ir(III) catalyst also promoted the cycloisomerization of nitrogen-tethered 1,6-enynes to give azabicyclo[4.1.0]heptenes, enhancing the synthetic potential of our method. Copyright

A study of (binap)(enyne)tetracarbonyldicobalt(0) complexes

Four (binap)(enyne)tetracarbonyldicobalt(0) complexes have been synthesised and their reactivity monitored by variable temperature 31P NMR spectroscopy. Formation of (binap)dicarbonylhydridocobalt(-1) 12 occurred at temperatures between 35 and

Cobalt carbonyl-mediated carbocyclizations of enynes: Generation of bicyclooctanones or monocyclic alkenes

Depending on the thermolytic conditions, dicobalthexacarbonyl-complexed enynes underwent cyclizations to provide different carbocyclic frameworks. Bicyclopentanones were formed from enyne-Co2(CO)6 complexes, or from enynes that were treated with Co2(CO)8, or more effectively, with Co4(CO)12 in an alcoholic solvent under a H2 or N2 atmosphere. This transformation proceeded via a sequential cyclocarbonylation and 1,4-reduction and is the first account using the cobalt carbonyl cluster. Under these conditions a cobalt hydride was presumably generated, which mediated reduction of the enone to the saturated ketone. In contrast, thermolysis of dicobalthexacarbonyl-complexed enynes under a hydrogen atmosphere in toluene resulted in their reductive cyclization to form monocyclic alkenes in moderate yields, in addition to the bicyclopentenone product. In some cases, addition of a hydrosilane to the reaction induced a complete suppression of the bicyclopentenone formation. While the former results demonstrate a reaction that occurs after the cycloaddition, the latter depicts another example of an interruption of the normal route in the Pauson-Khand reaction pathway.

The reaction of triphenylstannylcobaloxime with enynes under photochemical and thermal conditions

Enynes having the 4-oxa-6-en-1-yne, 4-tosylaza-6-en-1-yne and 5-oxa-7-en-1-yne system, and 5,7-dioxa-l-octyne were reacted with triphenylstannylcobaloxime, which is a source of the triphenylstannyl radical and cobaloxime radical. The reaction pattern is different under photochemical and thermal conditions. Photochemical reaction gave the products formed by the addition of the triphenylstannyl radical to the acetylene group followed by the tandem addition of the intermediate vinyl radical to the intramolecular olefin. Thermal reaction gave triphenylstannyl-substitution products at the terminal position of the acetylene moiety. Thus, the photochemical reaction takes a free radical pathway, and the thermal reaction is proposed to take a single electron transfer mechanism.