1361582-91-3

Upstream product

• 69116-22-9 1-(iodoethynyl)-4-nitrobenzene 
• 1361583-02-9 N-(3-bromobut-3-en-1-yl)-4-methylbenzenesulfonamide 
• 591-50-4 iodobenzene 
• 1374005-93-2 C₁₃H₁₄BrNO₂S 
• 1361583-12-1 N-(3-bromobut-3-en-1-yl)-4-methyl-N-((trimethylsilyl)ethynyl)benzenesulfonamide 

Downstream Products

• 1361582-56-0 5-cyclohexyl-7-(4-nitrophenyl)-1-tosyl-2,3,4,5-tetrahydro-1H-indole 

Relevant academic research and scientific papers

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.

Palladium-catalyzed cascade cyclization of ynamides to azabicycles

Cascade reactions: A modular assembly of azabicycles by using a cascade cyclization/Suzuki coupling/6π-electrocyclization of bromoenynamides is reported (see scheme). The reaction offers a wide substituent scope on the bicyclic aminodiene products, which can be selectively oxidized as a general approach to aromatic azabicycles.