5548-09-4Relevant articles and documents
A tryptophan-analog host whose interactions with ammonium ions in water are dominated by the hydrophobic effect
Whiting, Amanda L.,Neufeld, Nicole M.,Hof, Fraser
, p. 7035 - 7037 (2009)
The binding of quaternary ammonium guests to a flexible, indole-based host has been studied in both aqueous and organic solvents. Binding was shown to depend strongly on the hydrophobic effect and less on the cation-π interaction.
Defunctionalization of sp3 C–Heteroatom and sp3 C–C Bonds Enabled by Photoexcited Triplet Ketone Catalysts
An, Juzeng,Gu, Yiting,Martin, Ruben,Wakeling, Matthew,Yin, Hongfei
, p. 1031 - 1036 (2022/01/19)
A general strategy for enabling a light-induced defunctionalization of sp3 C–heteroatom and sp3 C–C bonds with triplet ketone catalysts and bipyridine additives is disclosed. This protocol is characterized by its broad scope without recourse to transition metal catalysts or stoichiometric exogeneous reductants, thus offering a complementary technique for activating σ sp3 C–C(heteroatom) bonds. Preliminary mechanistic studies suggest that the presence of 2,2′-bipyridines improves the lifetime of ketyl radical intermediates.
A Catalytic One-Pot Synthesis of Indolyl Cyclobutanones
Porcu, Stefania,Rodriguez, Carla Aira,Frongia, Angelo,Secci, Francesco
supporting information, p. 925 - 932 (2020/12/14)
A general strategy for the synthesis of indolyl cyclobutanones via a tandem Bronsted acid catalyzed 2-hydroxycyclobutanone activation-indole nucleophilic addition has been exploited. The procedure leads to a wide range of 2- and 3-functionalized indole derivatives in good to high yields with broad substrate scope.
Direct Deamination of Primary Amines via Isodiazene Intermediates
Berger, Kathleen J.,Driscoll, Julia L.,Yuan, Mingbin,Dherange, Balu D.,Gutierrez, Osvaldo,Levin, Mark D.
supporting information, p. 17366 - 17373 (2021/11/04)
We report here a reaction that selectively deaminates primary amines and anilines under mild conditions and with remarkable functional group tolerance including a range of pharmaceutical compounds, amino acids, amino sugars, and natural products. An anomeric amide reagent is uniquely capable of facilitating the reaction through the intermediacy of an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared to existing protocols, our approach enables strategic applications of iminium and amine-directed chemistries as traceless methods. Mechanistic and computational studies support the intermedicacy of a primary isodiazene which exhibits an unexpected divergence from previously studied secondary isodiazenes, leading to cage-escaping, free radical species that engage in a chain, hydrogen-atom transfer process involving aliphatic and diazenyl radical intermediates.