91130-46-0Relevant academic research and scientific papers
Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp3)-H Aminations with Unprotected Anilines
Evoniuk, Christopher J.,Gomes, Gabriel Dos Passos,Hill, Sean P.,Fujita, Satoshi,Hanson, Kenneth,Alabugin, Igor V.
supporting information, p. 16210 - 16221 (2017/11/22)
An intramolecular oxidative C(sp3)-H amination from unprotected anilines and C(sp3)-H bonds readily occurs under mild conditions using t-BuOK, molecular oxygen and N,N-dimethylformamide (DMF). Success of this process, which requires mildly acidic N-H bonds and an activated C(sp3)-H bond (BDE 85 kcal/mol), stems from synergy between basic, radical, and oxidizing species working together to promote a coordinated sequence of deprotonation: H atom transfer and oxidation that forges a new C-N bond. This process is applicable for the synthesis of a wide variety of N-heterocycles, ranging from small molecules to extended aromatics without the need for transition metals or strong oxidants. Computational results reveal the mechanistic details and energy landscape for the sequence of individual steps that comprise this reaction cascade. The importance of base in this process stems from the much greater acidity of transition state and product for the 2c,3e C-N bond formation relative to the reactant. In this scenario, selective deprotonation provides the driving force for the process.
Double C-H amination by consecutive SET oxidations
Evoniuk, Christopher J.,Hill, Sean P.,Hanson, Kenneth,Alabugin, Igor V.
supporting information, p. 7138 - 7141 (2016/06/09)
A new method for intramolecular C-H oxidative amination is based on a FeCl3-mediated oxidative reaction of anilines with activated sp3 C-H bonds. The amino group plays multiple roles in the reaction cascade: (1) as the activating group in single-electron-transfer (SET) oxidation process, (2) as a directing group in benzylic/allylic C-H activation at a remote position, and (3) internal nucleophile trapping reactive intermediates formed from the C-H activation steps. These multielectron oxidation reactions proceed with catalytic amounts of Fe(iii) and inexpensive reagents.
Iridium-catalyzed decarboxylative N-alkylation of α-amino acids with primary alcohols
Wu, Jiashou,Jiang, Huajiang,Chen, Dingben,Shen, Jianfen,Zhao, Datong,Xiang, Jing,Zhou, Qizhong
, p. 539 - 542 (2014/03/21)
A new decarboxylative N-alkylation reaction of α-amino acids has been developed. A variety of tertiary amines were obtained in good to excellent yields via the decarboxylative N-alkylation reaction of α-amino acids with primary alcohols catalyzed by a CpIr complex. Georg Thieme Verlag Stuttgart New York.
Chiral sulfoxide ligands bearing nitrogen atoms as stereocontrollable coordinating elements in palladium-catalyzed asymmetric allylic alkylations
Hiroi, Kunio,Suzuki, Yoshio,Abe, Ikuko,Hasegawa, Yutaka,Suzuki, Kenji
, p. 3797 - 3817 (2007/10/03)
Palladium-catalyzed asymmetric allylic alkylations were studied by using chiral sulfoxide ligands bearing nitrogen atoms as coordinating elements, such as chiral α-sulfinylacetamides, β or γ-amino sulfoxides, and β- sulfinyl sulfonamides. The effects of t
Development of Synthetic Compounds with Glutathione Peroxidase Activity
Wilson, Stephen R.,Zucker, Paul A.,Huang, Ruey-Ruey C.,Spector, Abraham
, p. 5936 - 5939 (2007/10/02)
Glutathione peroxidase is the major defense in the lens of the eye against hydrogen peroxide.The damage caused by hydrogen peroxide has been implicated in the formation of cataract.Organoselenium compounds which show catalytic activity in the enzyme assay
