83949-33-1Relevant articles and documents
Metal-free reductive cleavage of C-N and S-N bonds by photoactivated electron transfer from a neutral organic donor
O'Sullivan, Steven,Doni, Eswararao,Tuttle, Tell,Murphy, John A.
supporting information, p. 474 - 478 (2014/01/23)
A photoactivated neutral organic super electron donor cleaves challenging arenesulfonamides derived from dialkylamines at room temperature. It also cleaves a)ArC-NR and b)ArN-C bonds. This study also highlights the assistance given to these cleavage reactions by the groups attached to N in (a) and to C in (b), by lowering LUMO energies and by stabilizing the products of fragmentation. Radical fragmentations: Electron transfer from the photoactivated neutral electron donor 1 delivers high yields of S-N and C-N cleavage products for a range of nitrogen-containing species. These reactions proceed at room temperature and under mild reaction conditions in the absence of any metal reagents. DMF=N,N-dimethylformamide, Ts=4-toluenesulfonyl.
Chemoselective synthesis of N-substituted α-amino-α′- chloro ketones via chloromethylation of glycine-derived Weinreb amides
Pace, Vittorio,Holzer, Wolfgang,Verniest, Guido,Alcantara, Andres R.,De Kimpe, Norbert
supporting information, p. 919 - 926 (2013/05/08)
Functionalized α-arylamino-α′-chloro ketones are obtained in high yield via a straightforward homologation reaction of Weinreb amides derived from N-arylglycines using in situ generated chloromethyllithium. The use of the Weinreb amides is essential and allows the chemoselective homologation of N-aryl-N-substituted glycine analogues, a transformation which is not possible using similar glycine esters. The procedure is promising for the large-scale preparation of α-amino-α′-chloropropanones, which are valuable precursors for a variety of bioactive compounds. Copyright
