20114-58-3

Upstream product

• 492-21-7 9H-xanthene-9-thione 
• 127-65-1 chloroamine-T 
• 941-55-9 4-toluenesulfonyl azide 
• 92-83-1 xanthene 
• 70-55-3 toluene-4-sulfonamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 90-47-1 xanth-9-one 

Downstream Products

• 6326-06-3 4-methyl-N-(9H-xanthen-9-yl)benzenesulfonamide 
• 1334532-48-7 (R)-2-(9H-xanthen-9-yl)cyclohexanone 

Relevant academic research and scientific papers

Uncatalyzed Oxidative C?H Amination of 9,10-Dihydro-9-Heteroanthracenes: A Mechanistic Study

A new method for the one-step C?H amination of xanthene and thioxanthene with sulfonamides is reported, without the need for any metal catalyst. A benzoquinone was employed as a hydride (or two-electron and one-proton) acceptor. Moreover, a previously unknown and uncatalyzed reaction between iminoiodanes and xanthene, thioxanthene and dihydroacridines (9,10-dihydro-9-heteroanthracenes or dihydroheteroanthracenes) is disclosed. The reactions proceed through hydride transfer from the heteroarene substrate to the iminoiodane or benzoquinone, followed by conjugate addition of the sulfonamide to the oxidized heteroaromatic compounds. These findings may have important mechanistic implications for metal-catalyzed C?H amination processes involving nitrene transfer from iminoiodanes to dihydroheteroanthracenes. Due to the weak C?H bond, xanthene is an often-employed substrate in mechanistic studies of C?H amination reactions, which are generally proposed to proceed via metal-catalyzed nitrene insertion, especially for reactions involving nitrene or imido complexes that are less reactive (i.e., less strongly oxidizing). However, these substrates clearly undergo non-catalyzed (proton-coupled) redox coupling with amines, thus providing alternative pathways to the widely assumed metal-catalyzed pathways.

Organocatalytic nitrenoid transfer: Metal-free selective intermolecular C(sp3)-H amination catalyzed by an iminium salt

This report details the first organocatalytic method for nitrenoid transfer and its application to intermolecular, site-selective C(sp3)-H amination. The method utilizes a trifluoromethyl iminium salt as the catalyst, iminoiodinanes as the nitrogen source, and substrate as the limiting reagent. Activated, benzylic, and aliphatic substrates can all be selectively functionalized in yields up to 87%. A mechanistic proposal for the observed reactivity supported by experimental evidence invokes the intermediacy of a diaziridinium salt or related organic nitrenoid, species that have not been previously explored for the purpose of C-H amination. Finally, examples of late-stage functionalization of complex molecules highlight the selectivity and potential utility of this catalytic method in synthesis.

Catalytic asymmetric α-alkylation of ketones and aldehydes with N-benzylic sulfonamides through carbon-nitrogen bond cleavage

A range of ketones and aldehydes smoothly undergo asymmetric SN1 α-alkylation with N-benzylic sulfonamides in the presence of 10 mol % of a chiral imidazolidinone and trifluoroacetic acid to give the corresponding products in good to excellent

Reactions of dimethoxycarbene with N-tosylated imines

The reactions of dimethoxycarbene (DMC; 2), which was generated in situ by thermal decomposition of 2,5-dihydro-2,2-dimethoxy-5,5-dimethyl-l,3,4-oxadiazole (1), with N-tosylated imines of xanthone and 2,3:6,7-dibenzosuberenone, 3a and 3d, respectively, le

N-YLIDENBENZOLSULFONAMIDE AUS THIOXOHETEROCYCLEN UND PHENYLSULFONYLAZIDEN

Thioxoheterocycles (1-9) react with phenylsulfonylazides (10) to give N-ylidenebenzenesulfonamides (11-20).Key words: 2- and 4-pyridinethiones; 4-pyranthiones; 1,4-dimethylpiperazine-2,5-dithione; phenylsulfonylazides, N-ylidenebenzenesulfonamides.