Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides
The synthesis of α-amino carbonyl/carboxyl compounds is a contemporary challenge in organic synthesis. Herein, we present a stereoselective α-amination of amides employing simple azides that proceeds under mild conditions with release of nitrogen gas. The
Tona, Veronica,De La Torre, Aurélien,Padmanaban, Mohan,Ruider, Stefan,González, Leticia,Maulide, Nuno
supporting information
p. 8348 - 8351
(2016/07/26)
Iron-catalyzed oxidative amidation of tertiary amines with aldehydes
Unconventional couple: A new oxidative coupling protocol for amide bond formation has been developed (see scheme). The method provides an efficient and practical route for the synthesis of tertiary amides from readily available tertiary amines and aldehydes in the presence of a simple FeCl2 catalyst. Mechanistic studies indicated that a peroxide and an iminium ion act as the reactive intermediates in this oxidative amidation.
Li, Yuanming,Jia, Fan,Li, Zhiping
supporting information
p. 82 - 86
(2013/03/13)
Niobium pentachloride promoted conversion of carboxylic acids to carboxamides: Synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures
A practical method for the conversion of carboxylic acids to the corresponding carboxamides mediated by niobium pentachloride under mild conditions is described. The synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures was accomplished via benzylic lithiation of N-methyl-3,4-dimethoxy-2-(4′-methoxybenzyl)benzamide.
Nery, Marcelo S.,Ribeiro, Renata P.,Lopes, Claudio C.,Lopes, Rosangela S. C.
p. 272 - 276
(2007/10/03)
Reaction of tert-Butyl Dibromoacetate or N,N-Diethyldibromoacetamide with Trialkylmanganate Providing an Alkylated Manganese Enolate
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Inoue, Rie,Shinokubo, Hiroshi,Oshima, Koichiro
p. 910 - 911
(2007/10/03)
Ruthenium Tetroxide Oxidation of N-Acylated Alkylamines: A New General Synthesis of Imides
Oxidation of various N-acylalkylamines with ruthenium tetroxide (RuO4) was systematically investigated.N-acylalkylamines having an electron-donating group at the α- or β-position with respect to amide nitrogen or an electron-donating alkyl function in the acyl group were smoothly oxidized to the corresponding imides in excellent yields.On the other hand, N-acylalkylamines having an electron-withdrawing group were not oxidized at all, and most of the starting material was recovered.It appears that the reactivity of N-acylalkylamines is closely correlated with the acidity of the carboxylic acid from which the N-acyl group is derived, and also with the electron density at the methylene moiety adjacent to the amide nitrogen atom.Keywords---oxidation; ruthenium tetroxide oxidation; imide synthesis; acyclic imide; amide; ruthenium tetroxide; substituent effect