136175-22-9

Upstream product

• 938-16-9 2,2-dimethylpropiophenone 
• 65855-34-7 2-tert-butyl-2-phenyl-aziridine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 90-47-1 xanth-9-one 
• 65855-34-7 2-tert-butyl-2-phenyl-aziridine 
• 4381-14-0 9,9'-bixanthene 
• 136175-27-4 2-tert-butyl-3-(9-xanthenyl)-2-phenylaziridine 
• 136201-62-2 9-<3,3-dimethyl-2-phenyl-2-(4-tolylsulfonamido)butyl>xanthene 
• 769-57-3 α,β,β-trimethylstyrene 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 107524-67-4 2,3-diphenyl-2-methylbutane 
• 70-55-3 toluene-4-sulfonamide 
• 726-18-1 4,4'-dianisylmethane 
• 86429-26-7 (+/-)-3,3-dimethyl-2-phenylbutanal 
• 136175-25-2 9-<3,3-dimethyl-2-phenyl-2-(4-tolylsulfonamido)butyl>-9,10-dihydroanthracene 

Relevant academic research and scientific papers

Electron-deficient olefin ligands enable generation of quaternary carbons by Ni-catalyzed cross-coupling

A Ni-catalyzed Negishi cross-coupling with 1,1-disubstituted styrenyl aziridines has been developed. This method delivers valuable β-substituted phenethylamines via a challenging reductive elimination that affords a quaternary carbon. A novel electron-deficient olefin ligand, Fro-DO, proved crucial for achieving high rates and chemoselectivity for C-C bond formation over β-H elimination. This ligand is easy to access, is stable, and presents a modular framework for reaction discovery and optimization. We expect that these attributes, combined with the fact that the ligands impart distinct electronic properties to a metal, will support the invention of new transformations not previously possible using established ligands.

N-S Cleavage Is Faster Than Homolytic Ring Opening in Single-Electron Transfer to Some N-Sulfonylaziridines. Competition between SN2 and SET

The radical anions of the N-sulfonylaziridines, 1a,b and 3 undergo N-S cleavage in place of homolytic ring opening as is demonstrated by reactions with anthracenide A*-.Nucleophilic ring opening of the sulfonylaziridines 1a,b and 3 by the carbanions AH-, X-, and Fl- of dihydroanthracene, xanthene, and fluorene, respectively, proceeds with the expected regioselectivity and is slow enough to allow some competition by a single-electron transfer (SET) initiated N-S cleavage, which provides the desulfonated aziridines and bixanthenyl X-X or bifluorenyl Fl-Fl, respectively.The SET path is favored by light.The competition is in favor of SET to the exclusion of the nucleophilic opening when trityl anion reacts with 1a.The twice-found byproducts 11 and 12 require the azirine intermediate 15, which is, at least formally, generated by elimination of TsH from 1a in a non-SET reaction.