953053-97-9

Upstream product

• 1859-70-7 N-(2-acetylphenyl)-4-methylbenzenesulfonamide 
• 593-56-6 N-methoxylamine hydrochloride 
• 953053-99-1 ethyl-(2E)-4-[[(4-methylphenyl)sulfonyl][2-[1-(1E)-(methoxyimino)ethyl]phenyl]amino]-2-butenoate 
• 941-55-9 4-toluenesulfonyl azide 
• 3376-33-8 O-methyl acetophenone oxime 
• 98-59-9 p-toluenesulfonyl chloride 
• 15754-20-8 (E)-acetophenone O-methyloxime 
• 551-93-9 2-aminoacetophenone 

Downstream Products

• 953053-99-1 ethyl-(2E)-4-[[(4-methylphenyl)sulfonyl][2-[1-(1E)-(methoxyimino)ethyl]phenyl]amino]-2-butenoate 

Relevant academic research and scientific papers

Iridium-catalyzed direct arene C-H bond amidation with sulfonyl- and aryl azides

Iridium-catalyzed direct ortho C-H amidation of arenes has been shown to work well with sulfonyl- and aryl azides as the nitrogen source. The reaction proceeds efficiently with a broad range of substrates bearing conventional directing groups with excellent functional group compatibility under mild conditions. In addition, substrates forming not only 5- but also 6-membered iridacycle intermediates undergo the C-H amidation with high selectivity.

Ruthenium-catalyzed direct C-H amidation of arenes including weakly coordinating aromatic ketones

C-H activation: The ruthenium-catalyzed direct sp2 C-H amidation of arenes by using sulfonyl azides as the amino source is presented (see scheme). A wide range of substrates were readily amidated including arenes bearing weakly coordinating groups. Synthetic utility of the thus obtained products was demonstrated in the preparation of biologically active heterocycles. Copyright

Rhodium-catalyzed intermolecular amidation of arenes with sulfonyl azides via chelation-assisted C-H bond activation

We report the direct amidation of arene C-H bonds using sulfonyl azides as the amino source to release N2 as the single byproduct. The reaction is catalyzed by a cationic rhodium complex under external oxidant-free conditions in the atmospheric environment. A broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thus opening a new avenue to practical intermolecular C-N bond formation.

Development of radical addition-cyclization-elimination reaction of oxime ether and its application to formal synthesis of (±)-martinelline

Radical addition-cyclization-elimination (RACE) reaction of oxime ether carrying unsaturated ester provides a novel method for the construction of pyrroloquinoline. Treatment of oxime ethers with Bu3SnH and AIBN gave N-norpyrroloquinoline as a major product, which was also obtained by the radical reaction of the corresponding hydrazone and imine. The radical reaction of aldehyde and ketone carrying unsaturated ester proceeded stereoselectively to give cis-furoquinolines and cis-hydroxyesters. The RACE reactions by using each of Bu3SnNMe2, Bu3SnD, and/or D2O were also examined in order to propose a reaction pathway to N-norpyrroloquinoline. Furthermore, the synthetic utility of RACE reaction is demonstrated by preparation of a key intermediate for the synthesis of (±)-martinelline.