2532-72-1Relevant academic research and scientific papers
Chemo- and regioselective reductive opening of azetidinium ions
Couty, Fran?ois,David, Olivier,Durrat, Fran?ois
, p. 1027 - 1031 (2007)
Enantiomerically pure azetidinium trifluoromethanesulfonates were opened by various hydride reagents. LiAlH4 and NaBH3CN reacted with a complete regioselectivity and the latter reagent also reacted in a chemoselective way, leaving un
Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups
Amberchan, Gabriella,Snelling, Rachel A.,Moya, Enrique,Landi, Madison,Lutz, Kyle,Gatihi, Roxanne,Singaram, Bakthan
supporting information, p. 6207 - 6227 (2021/05/06)
The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.
A practical catalytic reductive amination of carboxylic acids
Andrews, Keith G.,Denton, Ross M.,Hirst, David J.,Stoll, Emma L.,Tongue, Thomas,Valette, Damien
, p. 9494 - 9500 (2020/10/02)
We report reductive alkylation reactions of amines using carboxylic acids as nominal electrophiles. The two-step reaction exploits the dual reactivity of phenylsilane and involves a silane-mediated amidation followed by a Zn(OAc)2-catalyzed amide reduction. The reaction is applicable to a wide range of amines and carboxylic acids and has been demonstrated on a large scale (305 mmol of amine). The rate differential between the reduction of tertiary and secondary amide intermediates is exemplified in a convergent synthesis of the antiretroviral medicine maraviroc. Mechanistic studies demonstrate that a residual 0.5 equivalents of carboxylic acid from the amidation step is responsible for the generation of silane reductants with augmented reactivity, which allow secondary amides, previously unreactive in zinc/phenylsilane systems, to be reduced.
Diisobutylaluminum borohydride: An efficient reagent for the reduction of tertiary amides to the corresponding amines under ambient conditions
Snelling, Rachel A.,Amberchan, Gabriella,Resendez, Angel,Murphy, Chris L.,Porter, Lauren,Singaram, Bakthan
, p. 4073 - 4077 (2017/09/28)
A synthetically simple mixed metal hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], is easily generated from a 1:1 mixture of borane-dimethylsulfide (BMS) and diisobutylaluminum hydride (DIBAL). The reduction of tertiary amides using (iBu)2AlBH4 is complete within five minutes under ambient conditions and the product tertiary amines were isolated in 70–99% yields by a simple acid-base extraction. This new methodology, reported herein, works well for reduction of tertiary aliphatic and aromatic amides as well as lactams to the corresponding amines and product isolation and purification does not require column chromatography.
Symbiotic Transition-Metal and Organocatalysis for Catalytic Ambient Amine Oxidation and Alkene Reduction Reactions
Murray, Alexander T.,King, Rose,Donnelly, Joseph V. G.,Dowley, Myles J. H.,Tuna, Floriana,Sells, Daniel,John, Matthew P.,Carbery, David R.
, p. 510 - 514 (2016/02/20)
A new oxidation reaction based on two simple catalysts, namely, alloxan and a CuI salt, is highly effective for the aerobic oxidation and oxidative cross-coupling of amines. The reaction is operationally simple, reaction atmospheres enriched in dioxygen are obviated, and neither catalyst component requires prior synthesis. Mechanistic investigations have been performed and point towards a complex reaction manifold with evidence that supports a catalytic cycle that does not proceed through a quinone-imine step. Additionally, this dual catalyst system is efficient to effect diimide-mediated hydrogenation reactions of alkenes and alkynes, a transformation that has not been reported previously in the context of quinone catalyst systems.
METHOD OF PRODUCING TERTIARY AMINE OR TERTIARY AMINE DERIVATIVE
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Paragraph 0059; 0060, (2018/10/31)
PROBLEM TO BE SOLVED: To provide a method of producing tertiary amine or tertiary amine derivative with high selectivity. SOLUTION: In the method of producing tertiary amine or tertiary amine derivative, a reaction system including: an organic chemical raw material containing at least one kind of group selected from -NH2, -NH2 HCl, >NH and >NH HCl, a nitrogen atom contained in the group bounding to a carbon atom; aliphatic alcohol having 1 to 20 carbon atoms; and a catalyst where a carrier containing titanium oxide carries a silver component (metal silver or silver compound), is irradiated with light, and the group in the organic compound raw material is converted to -NR02 or >NR0, ( R0 is an aliphatic hydrocarbon group having 1 to 20 carbon atoms derived from the aliphatic alcohol). The percentage content of the silver in the catalyst is 0.5 to 10 mass% with respect to the titanium oxide. COPYRIGHT: (C)2015,JPOandINPIT
C-F bond substitution via aziridinium ion intermediates
Tr?ff,Janjetovic,Hilmersson
supporting information, p. 13260 - 13263 (2015/08/24)
Aliphatic 1,2-aminofluorides undergo extremely fast substitution reactions under the influence of lanthanum tris(hexamethyldisilazide). The substitution proceeds via an in situ generated aziridinium ion intermediate, which subsequently undergoes ring opening by addition of a nucleophile, yielding various β-substituted amines.
Iridium-catalysed amine alkylation with alcohols in water
Saidi, Ourida,Blacker, A. John,Farah, Mohamed M.,Marsden, Stephen P.,Williams, Jonathan M. J.
supporting information; experimental part, p. 1541 - 1543 (2010/06/12)
Amines have been directly alkylated with alcohols using 1 mol% [Cp*IrI2]2 catalyst in water in the absence of base or other additives. The Royal Society of Chemistry 2010.
Latent inhibitors of aldehyde dehydrogenase as alcohol deterrent agents
Nagasawa,Elberling,DeMaster
, p. 1335 - 1339 (2007/10/02)
A series of compounds structurally related to pargyline (N-methyl-N-propargylbenzylamide) were synthesized with the propargyl group replaced by a cyclopropyl, allyl, or 2,2,2-trichloroethyl group and, additionally in several cases, with the methyl group r
