60914-90-1Relevant articles and documents
Uncatalyzed Oxidative C?H Amination of 9,10-Dihydro-9-Heteroanthracenes: A Mechanistic Study
van Leest, Nicolaas P.,Grooten, Lars,van der Vlugt, Jarl Ivar,de Bruin, Bas
, p. 5987 - 5993 (2019)
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.
Catalytic asymmetric α-alkylation of ketones and aldehydes with N-benzylic sulfonamides through carbon-nitrogen bond cleavage
Weng, Zhen-Tao,Li, Yuan,Tian, Shi-Kai
experimental part, p. 8095 - 8099 (2011/11/07)
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
