80122-73-2

Upstream product

• 101110-81-0 (E)-3-(4-(tosyloxy)phenyl)prop-2-enoic acid 
• 80459-48-9 4-tosyloxybenzaldehyde 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 98-59-9 p-toluenesulfonyl chloride 
• 1109280-50-3 4-ethynylphenyl 4-methylbenzene-1-sulfonate 

Downstream Products

• 1215017-11-0 C₂₇H₂₄FNO₇S₃ 
• 944249-84-7 (2E)-3-[4-(toluene-4-sulfonyloxy)phenyl]-2-propenoic acid ethyl ester 
• 1262757-65-2 C₂₇H₂₅NO₇S₃ 
• 106951-34-2 1-(1,2-dibromo-ethyl)-4-(toluene-4-sulfonyloxy)-benzene 

Relevant academic research and scientific papers

Copper-Catalyzed Trifluoromethylthio-arylsulfonylation of Styrene Derivatives via the Insertion of Sulfur Dioxide

A copper-catalyzed four-component trifluoromethylthio-arylsulfonylation between styrene derivatives, AgSCF3, aryldiazonium tetrafluoroborates, and ex situ generated sulfur dioxide (from SOgen) is presented. This reaction features mild reaction conditions, good functional group tolerance, a broad substrate scope, good yields, and excellent diastereoselectivity. Preliminary mechanistic studies revealed that a radical process might be involved in this transformation.

Direct trans-Selective Ruthenium-Catalyzed Reduction of Alkynes in Two-Chamber Reactors and Continuous Flow

An efficient trans-selective hydrogenation of alkynes under low hydrogen pressure and low reaction temperatures is reported, applying a commercially available ruthenium hydride complex. The developed reaction conditions, which tolerate a variety of functional groups, are carried out in a two-chamber setup with ex situ generated hydrogen. The reaction setup is highly suitable for deuterium labeling. The trans-selective hydrogenation was extrapolated to a transfer hydrogenation protocol, employing a packed bed immobilized ruthenium hydride catalyst in continuous flow with a retention time of only 10 min.

Generation of stoichiometric ethylene and isotopic derivatives and application in transition-metal-catalyzed vinylation and enyne metathesis

Ethylene is one of the most important building blocks in industry for the production of polymers and commodity chemicals. 13C- and D-isotope-labeled ethylenes are also valuable reagents with applications ranging from polymer-structure determination, reaction-mechanism elucidation to the preparation of more complex isotopically labeled compounds. However, these isotopic derivatives are expensive, and are flammable gases, which are difficult to handle. We have developed a method for the controlled generation of ethylene and its isotopic variants including, for the first time, fully isotopically labeled ethylene, from simple alkene precursors by using Ru catalysis. Applying a two-chamber reactor allows both the synthesis of ethylene and its immediate consumption in a chemical transformation permitting reactions to be performed with only stoichiometric amounts of this two carbon olefin. This was demonstrated in the Ni-catalyzed Heck reaction with aryl triflates and benzyl chlorides, as well as Ru-mediated enyne metathesis. Why more when less works! A method for the controlled generation of ethylene including the fully isotopically labeled derivative is described, as well as their use in three transition-metal-catalyzed reactions. Applying a two-chamber reactor, only stoichiometric amounts of ethylene are required, which allows the simple installment of deuterium and 13C in the product (see scheme).

Oxidative alkoxycarbonylation of terminal alkenes with carbazates

A range of terminal alkenes smoothly underwent palladium-catalyzed oxidative alkoxycarbonylation with carbazates under an oxygen atmosphere to afford structurally diverse α,β-unsaturated esters in moderate to good yields with excellent regioselectivity and E selectivity.