51353-26-5Relevant academic research and scientific papers
Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride
Cheng, Hong-Gang,Pu, Maoping,Kundu, Gourab,Schoenebeck, Franziska
supporting information, p. 331 - 334 (2019/12/30)
We herein disclose the use of tetramethylammonium fluoride (TMAF) as a direct and selective methylating agent of a variety of amides, indoles, pyrroles, imidazoles, alcohols, and thiols. The method is characterized by operational simplicity, wide scope, and ease of purification. Our computational studies suggest a concerted methylation-deprotonation as the preferred reaction pathway.
Scope and mechanistic studies of catalytic hydrosilylation with a high-valent nitridoruthenium(VI)
Abbina, Srinivas,Bian, Shi,Oian, Casey,Du, Guodong
supporting information, p. 678 - 684 (2013/05/21)
Hydrosilylation catalyzed by a high-valent nitridoruthenium(VI) compound, [RuN(saldach)(CH3OH)]+[ClO4]- (1, where saldach is the dianion of racemic N,N'-cyclohexan-diyl- bis(salicylideneimine)) is described. Using phenylsilane as reductant, a variety of unsaturated organic substrates, including aldehydes, ketones, and imines, are effectively reduced to alcohols and amines, respectively, accompanied by the redistribution of PhSiH3 at silicon. Mechanistic studies indicate that the catalysis proceeds via silane activation rather than carbonyl activation, and the silane is likely activated via multiple pathways, including a radical-based pathway.
Iridium-catalyzed reduction of secondary amides to secondary amines and imines by diethylsilane
Cheng, Chen,Brookhart, Maurice
, p. 11304 - 11307 (2012/09/05)
Catalytic reduction of secondary amides to imines and secondary amines has been achieved using readily available iridium catalysts such as [Ir(COE) 2Cl]2 with diethylsilane as reductant. The stepwise reduction to secondary amine proceeds through an imine intermediate that can be isolated when only 2 equiv of silane is used. This system requires low catalyst loading and shows high efficiency (up to 1000 turnovers at room temperature with 99% conversion have been attained) and an appreciable level of functional group tolerance.
A biomimetic electrocatalytic system for the atom-economical chemoselective synthesis of secondary amines
Largeron, Martine,Fleury
supporting information; experimental part, p. 883 - 886 (2009/07/25)
A facile one-pot oxidation-imine formation-reduction route to secondary amines can be achieved electrolytically from primary amines. This atom-economical 1ox-mediated sequence, leaving ammonia as the sole byproduct, allows the rapid chemoselect
Generation of stable synthetic equivalents of unstable α-alkoxyacetaldehydes: An improved preparation of dirithromycin
McGill
, p. 1089 - 1091 (2007/10/02)
Described is the in situ preparation of the hemiacetals of α-alkoxyacetaldehydes. The hemiacetals are generated by hydrolysis of an acetal precursor in aqueous acetonitrile solutions. These hemiacetals serve as stable aldehyde equivalents, thus circumventing the production and isolation of unstable α-alkoxyaldehydes. The hemiacetal of 2-methoxyethoxyacetaldehyde is utilized in an effective and efficient preparation of Dirithromycin (LY237216).
Titanium Induced Coupling of Imines to Symmetrical Vicinal (R*,R*)-Diamines
Mangeney, P.,Tejero, T.,Alexakis, A.,Grosjean, F.,Normant, J.
, p. 255 - 257 (2007/10/02)
Symmetrical vicinal (R*,R*) -d,l-diamines were prepared from the corresponding imines and low valent titanium species generated by the action of titanium tetrachloride on amalgamated magnesium.
