335003-91-3

Upstream product

• 821-06-7 (E)-1,4-dibromobutene 
• 335004-29-0 (E)-N,N'-(but-2-ene-1,4-diyl)bis(4-methylbenzenesulfonamide) 
• 335004-22-3 (E)-N,N'-bis(tert-butyloxycarbonyl)-N,N'-bis[(4-methylphenyl)sulfonyl]-2-butene-1,4-diamine 
• 70-55-3 toluene-4-sulfonamide 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 63-74-1 sulfanilamide 
• 5438-30-2 (4-pyrrol-1-ylphenyl)sulfonamide 

Relevant academic research and scientific papers

Preparation of nitrogen-containing 25-membered pentaolefinic macrocycles: (E,E,E,E,E)-1,6,11,16,21-penta(arylsulfonyl)-1,6,11,16,21- pentaazacyclopentacosa-3,8,13,18,23-pentaenes

A stepwise preparation of a series of nitrogen-containing 25-membered pentaolefinic macrocycles is presented. The corresponding arenesulfonamides and trans-1,4-dibromo-2-butene served as precursors for the synthesis. Georg Thieme Verlag Stuttgart.

Syntheses, structures and redox properties of new macrocyclic triazatriolefinic Pd0 complexes and their polypyrrole modified electrodes - Application to heterogeneous catalytic Suzuki cross-coupling reactions

New triolefinic macrocyclic ligands of the type (E,E,E)-1,6,11- tris(arenesulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-triene (aryl: a = ferrocenyl, b = 4-pyrrol-1-ylphenyl, c = 4-methylphenyl) and their Pd 0 complexes (1aab, 1abb and 1bcc) have been prepared and characterized. Further structural characterization in the solid state has also been performed by means of X-ray diffraction analysis for the complex 1bcc. The redox properties of both the ligands and their Pd complexes have been studied using cyclic voltammetric and coulombimetric techniques. In particular, complexes and ligands containing the pyrrole group do polymerize upon exposure to sufficiently positive potentials, on glassy carbon electrodes, generating highly stable modified electrodes. The new modified electrodes are efficient and selective heterogeneous catalysts for Suzuki cross-couplings, benefiting from simple removal of the catalyst from the reaction vessel. As an example, more than 2·105 metal cycles are achieved at 65 °C in the coupling of phenylboronic acid and cinnamyl bromide. Iodoarenes and phenylboronic acid are also converted into biphenyls with relatively good conversions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Preparation of nitrogen-containing 15-membered triolefinic macrocycles: (E,E,E)-1,6,11-tris(arylsulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-trienes

Three routes to (E,E,E)-1,6,11-tris(arylsulfonyl)-1,6,11-triazacyclopentadeca-3,8,13-trienes are described. Optimization of the preparation of key intermediates has opened the way to efficient synthesis of a broad variety of 15-membered, nitrogen-containing triolefinic macrocycles.