1374005-94-3

Upstream product

• 5390-04-5 pent-1-yn-5-ol 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 92975-38-7 4-bromo-4-pentenoic acid tert-butyl ester 
• 64180-78-5 4-bromopent-4-en-1-ol 
• 1361583-16-5 N-(4-bromopent-4-en-1-yl)-4-methyl-N-((trimethylsilyl)ethynyl)benzenesulfonamide 

Downstream Products

• 1361582-88-8 N-(4-bromopent-4-en-1-yl)-4-methyl-N-(phenylethynyl)benzenesulfonamide 
• 1443365-81-8 dimethyl 8-phenyl-1-tosyl-1,2,3,4,5,8-hexahydroquinoline-6,7-dicarboxylate 
• 888488-10-6 4-methyl-N-(pent-4-en-1-yl)-N-(phenylethynyl)benzenesulfonamide 
• 1443365-64-7 (Z)-2-benzylidene-3-methylene-1-tosylpiperidine 

Relevant academic research and scientific papers

Reductive cyclization of bromoenynamides with alcohols as hydride source: Synthesis and reactions of 2-amidodienes

Under basic conditions in alcoholic solvents, bromoenynamides undergo palladium-catalyzed cyclization to cyclic 2-amidodienes in good to excellent yields. This process represents the first use of an alcohol as a hydride source in an alkyne carbopalladation/termination sequence, with the site selectivity of the reduction showing a strong dependence on the tethering ring size (5-8), and the nature of the alcohol and base. Reaction of the dienes with a range of dienophiles (including alkenes, alkynes and arynes) under various conditions gives bi- and tricyclic azacycles, which can be further oxidized to the aromatic azacycles. Copyright

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.