1298086-85-7

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 624-31-7 4-tolyl iodide 
• 2450-71-7 Propargylamine 
• 189031-66-1 N-(tert-butoxycarbonyl)-4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 1609632-72-5 ethyl 3,3-bis(N-(3-(p-tolyl)prop-2-ynyl)-4-methylphenylsulfonamido)acrylate 
• 1311184-71-0 4-methyl-N-(2-methylallyl)-N-(3-(p-tolyl)prop-2-yn-1-yl)benzenesulfonamide 
• 1217435-83-0 3-iodo-4-(4'-methylphenyl)quinoline 

Relevant academic research and scientific papers

NaBArF4-Catalyzed Oxidative Cyclization of 1,5- and 1,6-Diynes: Efficient and Divergent Synthesis of Functionalized γ- and δ-Lactams

An efficient NaBArF4-catalyzed oxidative cyclization of readily available 1,5- and 1,6-diynes has been developed. Importantly, this transition metal-free oxidative catalysis proceeds via a presumable Lewis acid-catalyzed SN2’ pathway, which is distinct from the relevant oxidative rhodium and gold catalysis. This method leads to the facile and practical construction of a diverse range of synthetically useful γ- and δ-lactams in mostly good to excellent yields with broad substrate scope.

Alkyne Versus Ynamide Reactivity: Regioselective Radical Cyclization of Yne-Ynamides

Ynamides are typically more reactive than simple alkynes and olefins. However, a serendipitous observation revealed a rare case where the reactivity of simple alkynes exceeds that of ynamides. This led to the development of a unique sulfur-radical-triggered cyclization of yne-tethered ynamides, which involves attack of the alkyne by a thiyl radical followed by cyclization with the ynamide. A wide range of novel 4-thioaryl pyrroles that could tolerate common functional moieties and N-protecting groups were expediently constructed by this strategy. The current method contrasts with the typical cyclization of yne-ynamides, which involves the attack of the alkyne moiety by the ynamide core. Control experiments and DFT calculations supported the participation of the sulfur radical in the reaction and the regioselective cyclization. The synthetic potential of the substituted pyrroles is also discussed.

Gold-Catalyzed Annulations of N-Propargyl Ynamides with Anthranils with Two Distinct Chemoselectivities

Gold-catalyzed annulation of N-propargyl ynamides with anthranils can proceed by two distinct mechanisms. In the case of a terminal N-propargyl ynamide, its resulting α-imino gold carbene reacts with a tethered alkyne to generate a vinyl cation to enable hydrolysis, which ultimately yields a pyrrolo[2,3-b]quinoline derivative after treatment with p-toluenesulfonic acid. For an internal alkyne, its α-imino gold carbene reacts with a tethered alkyne via either a vinyl cation or an alkenylgold carbene; both paths ultimately lead to a 4-ketone-2-aminopyrrole derivative. Our mechanistic analysis indicates that water is a better nucleophile than anthranil for terminal ynamides, whereas water and anthranils are equally reactive for internal ynamides.

Enantioselective Gold(I)-Catalyzed Hydrative Cyclizations of N-Propargyl-ynamides into 3,6-Dihydropyridinones

This study discloses the first enantioselective variant of the gold(I)-catalyzed hydrative cyclizations of ynamides, which have been implemented by using bis-gold(I) complexes of chiral diphosphines. Starting from N-propargyl-ynamides and water in the presence of p-toluenesulfonic acid, the cyclization reactions afford N-tosyl-3,6-dihydropyridin-2(1H)-ones in good isolated yields and with high levels of stereocontrol (20 examples, enantiomeric ratios up to 94:6).

Cobalt-catalyzed (Z)-selective semihydrogenation of alkynes with molecular hydrogen

Cobalt-catalyzed highly (Z)-selective semihydrogenation of alkynes using molecular H2 was developed using commercially available and cheap cobalt precursors. A variety of (Z)-alkenes were obtained in moderate to excellent selectivities [(Z)-alkene/(E)-alkene/alkane ratio up to >99 : 1 : 1] and it was found that the readily available ethylenediamine ligand is crucial in determining the selectivity.

Palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: Facile synthesis of bicyclo[4.1.0]heptan-5-ones

We here describe a new palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes at room temperature using tBuONO as an oxidant for the synthesis of 3-bicyclo[4.1.0]heptan-5-ones. This cascade strategy involves the hydration, cyclization and cycl

Access to cyclobutene-fused azepines through au-catalyzed cycloisomerization of stable alkyne tethered ketene N,N -acetals

A base promoted reaction between N-protected propargyl amines and 3-bromopropiolate readily provides an array of novel stable alkyne-tethered ketene N,N-acetals in good yields. A wide range of structurally complex cyclobutene-fused azepine heterocycles are synthesized through the gold-catalyzed intramolecular cycloisomerization of ketene N,N-acetals for the first time. A plausible reaction pathway is deduced on the basis of the 1H NMR studies.

Gold(I)-catalyzed 6-endo-dig hydrative cyclization of an alkyne-tethered ynamide: Access to 1,6-dihydropyridin-2(3H)ones

Hydrate your chemistry! Hydrative cyclization of 5-yne-ynamides in the presence of Echavarren's catalyst and p-toluenesulphonic acid (PTSA)×H2O at room temperature affords an array of 1,6-dihydropyridin-2(3H)one derivatives. Isomerization, epoxidation, and hydrogenation of the double bond and insertion of an extended π-conjugate system into the pyridinone skeleton have been successfully accomplished (see scheme; Ts=tosyl). Copyright

Au(I)/Au(III)-catalyzed Sonogashira-type reactions of functionalized terminal alkynes with arylboronic acids under mild conditions

A straightforward, efficient, and reliable redox catalyst system for the Au(I)/Au(III)-catalyzed Sonogashira cross-coupling reaction of functionalized terminal alkynes with arylboronic acids under mild conditions has been developed.