309947-66-8

Upstream product

• 928-90-5 5-hexyl-1-ol 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 

Downstream Products

• 309947-68-0 4-methyl-N-(6-trimethylsilanyl-hex-5-ynyl)-benzenesulfonamide 
• 309947-70-4 4-methyl-N-trimethylsilanylethynyl-N-(6-trimethylsilanyl-hex-5-ynyl)-benzenesulfonamide 
• 1607830-05-6 N-(7-(benzyldimethylsilyl)hepta-1,6-diyn-1-yl)-N-(5-bromohex-5-en-1-yl)-4-methylbenzene sulfonamide 
• 1361582-69-5 9-hexyl-7-phenyl-1-tosyl-2,3,4,5,6,9-hexahydro-1H-benzo[b]azepine 
• 1443365-78-3 (Z)-2-heptylidene-3-methylene-1,5-ditosyl-1,5-diazocane 
• 1361582-89-9 N-(5-bromohex-5-en-1-yl)-4-methyl-N-(oct-1-yn-1-yl)benzenesulfonamide 
• 1443365-60-3 N-(5-bromohex-5-en-1-yl)-N-(5-((tert-butyldimethylsilyl)oxy)pent-1-yn-1-yl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

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.

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.

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.

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

Palladium-catalyzed cyclization of bromoenynamides to tricyclic azacycles: Synthesis of trikentrin-like frameworks

Palladium-catalyzed cascade cyclization of bromoenynamides equipped with an additional alkyne or ynamide substituent affords azatricyclic products. Using 5- to 7-membered ring tethers, this chemistry offers a regiospecific route to highly-functionalized azacycles. Elaboration to the trikentrin B skeleton is achieved from the arylsilane cyclization products. the Partner Organisations 2014.