138373-91-8Relevant articles and documents
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.
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.