133886-40-5

Upstream product

• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 106-96-7 propargyl bromide 
• 35466-83-2 allyl methyl carbonate 
• 107-19-7 propargyl alcohol 
• 70-55-3 toluene-4-sulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 107-18-6 allyl alcohol 
• 106-95-6 allyl bromide 
• 42268-68-8 allylpropargylamine 

Downstream Products

• 133886-43-8 2,3,3a,4-tetrahydro-2-[(4-methylphenyl)sulfonyl]-cyclopenta[c]pyrrol-5(1H)-one 
• 144365-79-7 1-[3-(Toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-propan-2-one 
• 187737-37-7 propene 
• 53146-16-0 tert-butylprop-2-enaldimine 
• 384836-11-7 N-allyl-4-methyl-N-(3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-yl)benzenesulfonamide 
• 172791-08-1 3,4-dimethyl-1-[(4-methylphenyl)sulfonyl]-2,5-dihydro-1H-pyrrole 

Relevant academic research and scientific papers

One-pot approach to access 2H-pyran-2-ones bearing an amino group via the Pd-catalyzed Sonogashira coupling of (Z)-3-iodovinylic esters followed by intramolecular iodocyclization

A one‐pot sequence of Sonogashira coupling and iodocyclization afforded novel amino-containing trisubstituted 2H-pyran-2-ones in good yields. This transformation proceeds via 1) synthesis of an ynenoic ester intermediate by a Sonogashira coupling reaction with an N-substituted (Z)-3-iodovinylic ester; 2) intramolecular iodocyclization of the latter intermediate under mildly basic conditions. The flexibility of this strategy enables the efficient syntheses of a variety of substituted 2H-pyran-2-ones.

Palladium-catalyzed cyclization-Heck reaction of allenamides: An approach to 3-methylene-5-phenyl-1,2,3,4-tetrahydropyridine derivatives

An efficient one-pot construction of functionalized 3-methylene-5-phenyl-1,2,3,4-tetrahydropyridine derivatives via palladium-catalyzed cyclization-Heck reaction of allenamides has been described. The 3-methylene-5-phenyl-1,2,3,4-tetrahydropyridine derivatives feature a nonconjugated diene, including one endo-enamine and one exocyclic double bond, which could be used for further transformation. Both aryl and vinyl halides performed very well under the standard conditions, delivering the corresponding products efficiently.

Intermolecular transition metal-catalyzed [4 + 2 + 2] cycloaddition reactions: A new approach to the construction of eight-membered rings

Transition metal-catalyzed cycloaddition reactions represent powerful methods for the construction of complex polycyclic systems. We have developed a new intermolecular metal-catalyzed [4 + 2 + 2] cycloaddition of heteroatom-tethered enyne derivatives wit

Tandem One-Pot Approach to N-Substituted Lactones by Carbon–Carbon Coupling Followed by 5-exo-dig or 6-endo-dig Cyclization: DFT Studies and Cyclization Mode

A one-pot approach has been developed for the preparation of a five or six-membered ring of unsaturated lactones bearing an amino group through a tandem coupling oxacyclization reaction. This tandem process involves Sonogashira-like cross-coupling followed by 5-exo-dig or 6-endo-dig intramolecular oxacyclization, according to the nature of the alkynes substituent. Furthermore, DFT calculations were performed to analyze the origin of this regioselectivity of cyclization.

A Free Radical Cyclization Catalyzed by Ruthenium Hydride Species

A photolytically generated ruthenium hydride species catalyzing a free radical cyclization reaction was developed. As the new methodology ensures reproducibility of the free radical reaction of trialkyltin hydrides and a fast hydrogen transfer to the radical intermediates, the methodology provides fast quenching of radical intermediates and thus suppresses rearrangement of radical intermediates before the hydride quench. By offering new reactivity and selectivity to the trialkyltin hydride mediated free radical cyclization reactions, the methodology will find wide range of applications in organic synthesis.

Cobalt-Catalyzed Enantioselective Hydroarylation of 1,6-Enynes

An asymmetric hydroarylative cyclization of enynes involving a C-H bond cleavage is reported. The cobalt-catalyzed cascade generates three new bonds in an atom-economical fashion. The products were obtained in excellent yields and excellent enantioselectivities as single diastereo- and regioisomers. Preliminary mechanistic studies indicate that the reaction shows no intermolecular C-H crossover. This work highlights the potential of cobalt catalysis in C-H bond functionalization and enantioselective domino reactivity.

Gold(I) Complexes Nuclearity in Constrained Ferrocenyl Diphosphines: Dramatic Effect in Gold-Catalyzed Enyne Cycloisomerization

Di-tert-butylated-bis(phosphino)ferrocene ligands bearing phosphino substituents R (R=phenyl, cyclohexyl, iso-propyl, mesityl, or furyl) allow tuning the selective formation of Au(I) halide complexes. Thus, dinuclear linear two-coordinate, but also rare mononuclear trigonal three-coordinate and tetrahedral four-coordinate complexes were formed upon tuning of the conditions. Both Au(I) chloride and rarer Au(I) iodide complexes were synthesized, and their X-ray diffraction analysis are reported. The significance of the control of structure and nuclearity in Au(I) complexes is further illustrated herein by its strong effect on the efficiency and selectivity of gold-catalysed cycloisomerization. Cationic linear digold(I) bis(dicyclohexylphosphino) ferrocenes outperform other catalysts in the demanding regioselective cycloisomerization of enyne sulphonamides into cyclohexadienes. Conversely, tetrahedral and trigonal cationic monogold(I) complexes were found incompetent for enyne cycloaddition. We used the two-coordinate linear electron-rich Au(I) complex 2 b (R=Cy) to extend the scope of selective intramolecular cycloaddition of different 1,6-enyne sulfonylamines with high activity and excellent selectivity to the endo cyclohexadiene products.

Asymmetric Reductive and Alkynylative Heck Bicyclization of Enynes to Access Conformationally Restricted Aza[3.1.0]bicycles

Conformationally restricted azabicycles are becoming increasingly important in medicinal research. Asymmetric Heck bicyclization of enynes proceeds to give medicinally useful aza[3.1.0] and aza[4.1.0] bicycles with excellent enantioselectivity. The key organopalladium species after bicyclization can be trapped by silanes and terminal alkynes.

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.

A palladium-catalyzed regiocontrollable hydroarylation reaction of allenamides with B2pin2/H2O

A novel palladium-catalyzed regiocontrollable hydroarylation reaction of allenamides with B2pin2/H2O has been disclosed. H2O as an ideal hydrogen source was activated by B2pin2 to furnish allylamines or enamines with a broad functional group tolerance. The regioselectivity for both of the two products was up to 99:1 for most of the examples, which was achieved by adjusting the addition order of the catalyst and iodobenzene derivatives. The tentative investigation of the mechanism proved the reaction to be a non-radical process and the deuterium-labeled experiments indicated that the hydrogen was from H2O.