309947-63-5

Upstream product

• 5390-04-5 pent-1-yn-5-ol 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 4083-64-1 Tosyl isocyanate 

Downstream Products

• 1361582-88-8 N-(4-bromopent-4-en-1-yl)-4-methyl-N-(phenylethynyl)benzenesulfonamide 
• 888488-10-6 4-methyl-N-(pent-4-en-1-yl)-N-(phenylethynyl)benzenesulfonamide 
• 1393361-27-7 tert-butyl 4-(cyclohexylidenemethyl)pent-4-enyl(tosyl)carbamate 
• 1310491-89-4 tert-butyl 5-phenylpent-4-ynyl(tosyl)carbamate 
• 1206670-56-5 C₁₇H₂₄⁽²⁾HNO₄S 
• 309947-69-1 4-methyl-N-trimethylsilanylethynyl-N-(5-trimethylsilanyl-pent-4-ynyl)-benzenesulfonamide 

Relevant academic research and scientific papers

Direct Intramolecular Aminoboration of Allenes

Direct intramolecular aminoboration of sulfonamidoallenes was realized using BCl3 as a boron source. The reactions benefited from the interaction between BCl3 and sulfonamides and provided a variety of borylvinyl heterocycles in good isolated yields. When chiral substrates were involved in the reactions, high stereoselectivity was observed, as can be ascertained by single-crystal X-ray diffraction experiments. Derivatization of the thus-obtained borylvinyl compounds proceeded readily, and different functionalities could be obtained via oxidation, halogenation, and Suzuki coupling reactions.

Dual Gold-Catalyzed Formal Tetradehydro-Diels–Alder Reactions for the Synthesis of Carbazoles and Indolines

This work reports a dual gold-catalyzed tetradehydro-Diels–Alder reaction for the synthesis of nitrogen-containing aromatic heterocycles. Under the catalytic system (IPrAuNTf2/DIPEA), indolines and carbazoles as well as other N-containing aromatic heterocycles were prepared in high yields with good functional group tolerance. Unlike the traditional thermal tetradehydro-Diels–Alder reactions, diluted reaction concentration and radical prohibitors are not required for this protocol. Experimental data support a mechanism involving gold vinylidene species, which undergoes a 6 π electrocyclization, followed with 1,2-hydrogen shift.

Tandem Gold-Catalyzed Dehydrative Cyclization/Diels-Alder Reactions: Facile Access to Indolocarbazole Alkaloids

A gold-catalyzed synthesis of cyclic 2-oxodienes from readily prepared propargyl alcohols and the subsequent Diels-Alder reaction are reported. The dehydrative cyclization reactions proceeded smoothly, and the dienes formed in situ were demonstrated to un

Ynamide Carbopalladation: A Flexible Route to Mono-, Bi- and Tricyclic Azacycles

Bromoenynamides represent precursors to a diversity of azacycles by a cascade sequence of carbopalladation followed by cross-coupling/electrocyclization, or reduction processes. Full details of our investigations into intramolecular ynamide carbopalladation are disclosed, which include the first examples of carbopalladation/cross-coupling reactions using potassium organotrifluoroborate salts; and an understanding of factors influencing the success of these processes, including ring size, and the nature of the coupling partner. Additional mechanistic observations are reported, such as the isolation of triene intermediates for electrocyclization. A variety of hetero-Diels-Alder reactions using the product heterocycles are also described, which provide insight into Diels-Alder regioselectivity.

Regio- and chemoselective n-1 acylation of indoles: Pd-catalyzed domino cyclization to afford 1,2-fused tricyclic indole scaffolds

A concise method for the synthesis of 1,2-fused tricyclic indole scaffolds by domino cyclization involving a Pd-catalyzed Sonogashira coupling, indole cyclization, regio- and chemoselective N-1 acylation, and 1,4-Michael addition is reported. This method

Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes

(Chemical Equation Presented) Homogeneous carboamination, carboalkoxylation and carbolactonization of terminal alkenes are realized via oxidative gold catalysis, providing expedient access to various substituted Nor O-heterocycles. Deuterium-labeling studies established the anti nature of the alkene functionalization and the indispensible role of Au(I)/Au(III) catalysis. This study constitutes the first example of catalytically converting C(sp 3)-Au bonds into C(sp3)-C(sp2) bonds in a crosscoupling manner and opens new opportunities to study gold alkene catalysis where alkylgold intermediates can be readily functionalized intermolecularly. Copyright

Asymmetric allylic alkylation in combination with ring-closing metathesis for the preparation of chiral N-heterocycles

Asymmetric copper-catalyzed allylic substitution with methylmagnesium bromide is employed in combination with ring-closing olefin metathesis or ene - yne metathesis to achieve the synthesis of chiral, unsaturated nitrogen heterocycles. The resulting six-

Tetrasubstituted pyrrolidines via a tandem aza-Payne/hydroamination reaction

A facile tandem aza-Payne/hydroamination reaction of aziridinol is reported, which yields highly functionalized pyrrolidines. Addition of alkynyl Grignards to 2,3-aziridinals yields, in most cases, high syn to anti ratios of the aziridinol. Treatment of the syn-aziridinol with base leads initially to an aza-Payne rearrangement, which juxtaposes the amine and the alkyne in favorable orientation to complete the hydroamination. The anti-aziridinol undergoes the aza-Payne rearrangement, but cannot proceed further with the hydroamination. Copyright

The Synthesis and Chemoselective Reactivity of 3-Aminocyclopentadienones

Iron and cobalt complexes of 3-aminocyclopentadienones have been synthesized from the [2 + 2 + 1] cycloadditions of nitrogen acetylenes and pendant alkynes. Following decomplexation, the resulting 3-aminocyclopentadienones have been subjected to chemo- and regioselective cycloadditions with dienophiles and heterodienes.