13626-20-5Relevant articles and documents
Photoinduced Olefin Diamination with Alkylamines
Angelini, Lucrezia,Govaerts, Sebastian,Hampton, Charlotte,Leonori, Daniele,Malet-Sanz, Laia,Ruffoni, Alessandro
supporting information, p. 15021 - 15028 (2020/06/17)
Vicinal diamines are ubiquitous materials in organic and medicinal chemistry. The direct coupling of olefins and amines would be an ideal approach to construct these motifs. However, alkene diamination remains a long-standing challenge in organic synthesis, especially when using two different amine components. We report a general strategy for the direct and selective assembly of vicinal 1,2-diamines using readily available olefin and amine building blocks. This mild and straightforward approach involves in situ formation and photoinduced activation of N-chloroamines to give aminium radicals that enable efficient alkene aminochlorination. Owing to the ambiphilic nature of the β-chloroamines produced, conversion into tetra-alkyl aziridinium ions was possible, thus enabling diamination by regioselective ring-opening with primary or secondary amines. This strategy streamlines the preparation of vicinal diamines from multistep sequences to a single chemical transformation.
Highly regioselective ring-opening of epoxides with amines: A metal- A nd solvent-free protocol for the synthesis of β-amino alcohols
Li, Dong,Wang, Jing,Yu, Shibo,Ye, Silei,Zou, Wenjie,Zhang, Hongbin,Chen, Jingbo
supporting information, p. 2256 - 2259 (2020/03/04)
We herein report a metal- A nd solvent-free acetic acid-mediated ring-opening reaction of epoxides with amines. This process provides β-amino alcohols in high yields with excellent regioselectivity. Importantly, this epoxide ring-opening protocol can be used for the introduction of amines in natural products during late-stage transformations.
Green Regio- and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent-Free Conditions
Acocella, Maria Rosaria,D'Urso, Luciana,Maggio, Mario,Guerra, Gaetano
, p. 1915 - 1920 (2016/07/06)
The ring-opening reactions of epoxides with amines were efficiently and regioselectively catalyzed by high-surface-area graphite and graphene oxide under metal-free and solvent-free conditions. For epoxides without aryl groups, catalytic activity was observed only for graphene oxide, and hence, the activity must have been due to its acidic groups. For styrene oxide, instead, graphite and graphene oxide exhibited rather similar catalytic activities, and hence, the activity was mainly due to activation of the electrophilic epoxide by π-stacking interactions with the graphitic π system. The described aminolysis procedure is green and cheap because the catalyst can be recovered and recycled without loss of efficiency. Moreover, these heterogeneous catalysts exert high stereoselective control in the presence of nonracemic epoxides and provide chiral β-amino alcohols with enantiomeric excess values up to 99 %.
