339540-95-3

Upstream product

• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 1521-51-3 rac-3-bromocyclohexene 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 98-59-9 p-toluenesulfonyl chloride 
• 57981-18-7 N-cyclohex-2-enyl-4-methyl-benzenesulfonamide 
• 107-19-7 propargyl alcohol 

Downstream Products

• 1164274-85-4 2,4,5,6,7,7a-hexahydro-3-(phenylsulfanylmethyl)-1-tosyl-1H-indole 
• 1262884-13-8 N-(cyclohex-2-en-1-yl)-N-(2-iodoallyl)-4-methylbenzenesulfonamide 
• 121224-77-9 1-(4'-methylphenylsulphonyl)-1-aza-3-methylidine bicyclo<4.3.0>nona-5-ene 

Relevant academic research and scientific papers

Alternating Cascade Metathesis Polymerization of Enynes and Cyclic Enol Ethers with Active Ruthenium Fischer Carbenes

Ruthenium alkoxymethylidene complexes have rarely been demonstrated as active species in metathesis reactions and are frequently regarded as inert. Herein, we highlight the ability of these Fischer-type carbenes to participate in cascade alternating ring-

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.

Rhodium(i)-catalyzed vinylation/[2 + 1] carbocyclization of 1,6-enynes with α-diazocarbonyl compounds

A sequential Rh(i)-catalyzed vinylation/[2 + 1]carbocyclization between enynes and diazo compounds has been developed. This transformation features a wide range of enynes and acceptor/acceptor diazo compounds, providing easy access to versatile vinyl-substituted azabicyclo[3.1.0]hexanes having a broad tolerance to functional groups.

Copper-catalyzed three-component cyanotrifluoromethylation/ azidotrifluoromethylation and carbocyclization of 1,6-enynes

A novel three-component strategy for the cyanotrifluoromethylation/ azidotrifluoromethylation and carbocyclization of 1,6-enynes is developed. The reaction proceeds smoothly under a moderate temperature by using a copper catalyst, which provides a rapid a

Tandem ring-opening/ring-closing metathesis polymerization: Relationship between monomer structure and reactivity

Monomers containing either cycloalkenes with low ring strain or 1-alkynes are poor monomers for olefin metathesis polymerization. Ironically, keeping two inactive functional groups in proximity within one molecule can make it an excellent monomer for metathesis polymerization. Recently, we demonstrated that monomer 1 having cyclohexene and propargyl moieties underwent rapid tandem ring-opening/ring-closing metathesis (RO/RCM) polymerization via relay-type mechanism. Furthermore, living polymerization was achieved when a third-generation Grubbs catalyst was used. Here, we present a full account on this tandem polymerization by investigating how various structural modifications of the monomers affected the reactivity of the tandem polymerization. We observed that changing the ring size of the cycloalkene moieties, the length of the alkynes, and linker units influenced not only the polymerization rates but also the reactivities of Diels-Alder reaction, which is a post-modification reaction of the resulting polymers. Also, the mechanism of tandem polymerization was studied by conducting end-group analysis using 1H NMR analysis, thereby concluding that the polymerization occurred by the alkyne-first pathway. With this mechanistic conclusion, factors responsible for the dramatic structure-reactivity relationship were proposed. Lastly, tandem RO/RCM polymerization of monomers containing sterically challenging trisubstituted cycloalkenes was successfully carried out to give polymer repeat units having tetrasubstituted cycloalkenes.

Selective ruthenium-catalyzed transformations of enynes with diazoalkanes into alkenylbicyclo[3.1.0]hexanes

Reaction of a variety of C≡CH bond-containing 1,6-enynes with N 2CHSiMe3 in the presence of RuCl(COD)Cp* as catalyst precursor leads, at room temperature, to the general formation of alkenylbicyclo[3.1.0]hexanes with high Z-stereosel

GaCl3-catalyzed formation of eight-membered rings from enynes bearing a cyclic olefin

GaCl3-catalyzed cycloisomerization of enynes having a cyclic olefin led to isolation of eight-membered ring compounds.

ROM-RCM of cycloalkene-yne

Ring-opening metathesis and ring-closing metathesis (ROM-RCM) of cycloalkene-yne was demonstrated using a first- or second-generation ruthenium complex. When cycloalkenes bearing the alkyne part at the C-3 position were reacted with a first-generation ruthenium-carbene complex under an atmosphere of ethylene, ROM-RCM proceeded smoothly to give skeletal reorganized products in good yields. In this reaction, cycloalkene-ynes having terminal alkyne were suitable. On the other hand, when cycloalkenes bearing the alkyne part at the C-1 position were treated with a second-generation ruthenium-carbene complex, ROM-RCM proceeded smoothly to give bicyclic compounds and/or dimeric compounds in good yields.

Cobalt Nanoparticles on Charcoal: A Versatile Catalyst in the Pauson-Khand Reaction, Hydrogenation, and the Reductive Pauson-Khand Reaction

(Matrix Presented) Dispersions of nanometer-sized cobalt particles with very high stability were prepared in charcoal and analyzed by electron microscopy and X-ray analysis. The resulting cobalt nanoparticles on charcoal (CNC) were successfully used as a catalyst for the carbonylative cycloaddition of alkyne, alkene, and carbon monoxide (Pauson-Khand reaction), hydrogenation, and the reductive Pauson-Khand reaction.