138373-91-8Relevant academic research and scientific papers
Photoredox Catalytic Three-Component Amidoazidation of 1,3-Dienes
Forster, Dan,Guo, Weisi,Wang, Qian,Zhu, Jieping
, p. 10871 - 10877 (2021)
In spite of the obvious synthetic potential of functionalized allylic azides, only limited synthetic routes have been developed. We report herein a three-component 1,2-amidoazidation of 1,3-dienes. In the presence offac-Ir(ppy)3under blue LED irradiation, reaction of 1-aryl substituted 1,3-dienes withN-amidopyridinium salt and trimethylsilyl azide (TMSN3) affords exclusively the 1,2-amidoazidation products. The 1-alkyl substituted counterparts undergo the same reaction with moderate to high 1,2- vs 1,4-selectivity. Reduction of this mixture with PPh3under dynamic kinetic conditions enriches significantly one of the two isomers thanks to the facile 1,3-azide shift (Winstein rearrangement) of the allyl azides.
Chemo- and Site-Selective Alkyl and Aryl Azide Reductions with Heterogeneous Nanoparticle Catalysts
Udumula, Venkatareddy,Nazari, S. Hadi,Burt, Scott R.,Alfindee, Madher N.,Michaelis, David J.
, p. 4423 - 4427 (2016/07/12)
Site-selective modification of bioactive natural products is an effective approach to generating new leads for drug discovery. Herein, we show that heterogeneous nanoparticle catalysts enable site-selective monoreduction of polyazide substrates for the generation of aminoglycoside antibiotic derivatives. The nanoparticle catalysts are highly chemoselective for reduction of alkyl and aryl azides under mild conditions and in the presence of a variety of easily reduced functional groups. High regioselectivity for monoazide reduction is shown to favor reduction of the least sterically hindered azide. We hypothesize that the observed selectivity is derived from the greater ability of less-hindered azide groups to interact with the surface of the nanoparticle catalyst. These results are complementary to previous Staudinger reduction methods that report a preference for selective reduction of electronically activated azides.
SYNTHESIS OF 1,2-AMINOAZIDES. CONVERSION TO UNSYMMETRICAL VICINAL DIAMINES BY CATALYTIC HYDROGENATION OR REDUCTIVE ALKYLATION WITH DICHLOROBORANES.
Benalil, Aziza,Carboni, Bertrand,Vaultier, Michel
, p. 8177 - 8194 (2007/10/02)
1,2-aminoazides are easily prepared from 1,2-amino alcohols.Catalytic hydrogenation in the presence of palladium on charcoal or reductive alkylation with dichloroboranes afford with good yields unsymmetrically substituted vicinal diamines.
