220165-50-4

Upstream product

• 49633-28-5 1,2-bis-(p-methylphenylsulfonamido)-benzene 
• 5332-81-0 carbonic acid (Z)-4-methoxycarbonyloxy-but-2-enyl ester methyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 220167-11-3 1,2,3,4-tetrahydro-2-vinylquinoxaline 
• 69627-35-6 N,N'-bis(benzenesulfonyl)-o-phenylenediamide 
• 220166-23-4 N,N'-(1,2-phenylene)bis(2,4,6-trimethylbenzenesulfonamide) 
• 109249-85-6 1,2-bis-(2-nitro-benzenesulfonylamino)-benzene 
• 95-54-5 1,2-diamino-benzene 
• 220166-48-3 N,N'-(1,2-phenylene)bis(4-methoxybenzenesulfonamide) 
• 220166-33-6 N,N'-(1,2-phenylene)bis(naphthalene-1-sulfonamide) 
• 220166-62-1 N,N'-bis(4-nitrophenyl)sulfonyl-o-phenylenediamine 
• 106-99-0 buta-1,3-diene 
• 115580-32-0 (Z)-but-2-ene-1,4-diyl di-tert-butyl dicarbonate 

Downstream Products

• 49633-27-4 2-hydroxymethyl-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-quinoxaline 

Relevant academic research and scientific papers

Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis

Palladium-catalyzed allylic substitution, or "Tsuji-Trost"reactions, can be run under micellar catalysis conditions featuring not only chemistry in water but also numerous combinations of reaction partners that require low levels of palladium, typically on the order of 1000 ppm (0.1 mol %). These couplings are further characterized by especially mild conditions, leading to a number of cases not previously reported in an aqueous micellar medium. Inclusion of diverse nucleophiles, such as N-H heterocycles, alcohols, dicarbonyl compounds, and sulfonamides is described. Intramolecular cyclizations further illustrate the broad utility of this process. In addition to recycling studies, a multigram scale example is reported, indicative of the prospects for scale up.

Pd(II)-Catalyzed Aerobic Intermolecular 1,2-Diamination of Conjugated Dienes: A Regio- and Chemoselective [4 + 2] Annulation for the Synthesis of Tetrahydroquinoxalines

A Pd(II)-catalyzed aerobic intermolecular 1,2-diamination of conjugated dienes was developed for the regio- and chemoselective preparation of a variety of functionalized tetrahydroquinoxalines, using simple sulfonyl protected o-phenylendiamines as a nitrogen source. This methodology provides a direct and efficient synthesis of tetrahydroquinoxalines. O2 was used as the stoichiometric oxidant, and reaction conditions were applied to a series of o-phenylendiamines and conjugated dienes. 35 examples are described, and good yields and selectivities are obtained for the majority of the products.

Palladium(0)-catalyzed asymmetric synthesis of 1,2,3,4-tetrahydro-2- vinylquinoxalines

Reaction of (Z)-1,2-bis(methoxycarbonyloxy)but-2-ene (2) with various N,N-bis(arylsulfonyl)-o-phenylenediamines 1 was catalyzed by a palladium complex associated with chiral ligands to give optically active 1,4- bis(arylsulfonyl)-1,2,3,4-tetrahydro-2-vinylquinoxalines 3 with up to 62% ee. The use of (S)-MeOBIPHEP as the chiral ligand and N,N-bis(p-tolylsulfonyl)-o- phenylenediamine (1i) as the nucleophile led to the highest ee at 25 °C, regardless of the solvent used. The enantioselectivity of the cyclization is strongly affected by the nature of the substituents at the nitrogen atom.