288325-45-1Relevant academic research and scientific papers
New approach for induction of alkyl moiety to aliphatic amines by NaBH(OAc)3 with carboxylic acid
Tamura, Satoru,Sugawara, Aoi,Sato, Erika,Sato, Fuka,Sato, Keigo,Kawano, Tomikazu
supporting information, (2020/04/15)
We had found the novel N-alkylation method, which utilizes carboxylic acids as alkyl sources with sodium triacetoxyborohydride [NaBH(OAc)3]. Our methodology had been revealed to have some advantages over the reported similar procedures. Through
Borane-trialkylamine hydroboration agents
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, (2008/06/13)
Borane-trialkylamines of the formula H3B.NRR1R2 wherein R is a tertiary alkyl group having 4 to 8 carbon atoms, and R1and R2are the same or different straight or branched chain alkyl from 1 to 4 carbon atoms are provided. The compounds are new hydroboration agents.
Molecular Addition Compounds. 16. New, Highly Reactive Borane Adducts with N,N-Dialkyl-tert-alkylamines for Hydroboration
Brown, Herbert C.,Kanth, Josyula V. B.,Dalvi, Pramod V.,Zaidlewicz, Marek
, p. 4655 - 4661 (2007/10/03)
Several N,N-diethyl-tert-alkylamines, such as N,N-diethyl-2-methyl-2-butylamine (1, t-PentNEt2), N,N-diethyl-2,3-dimethyl-2-butylamine (2, t-HexNEt2), N,N-diethyl-2,3,3-trimethyl-2-butylamine (3, t-HeptNEt2), and N,N-diethyl-1,1,3,3-tetramethylbutylamine (4, t-OctNEt2) with varying steric bulk around nitrogen (by changing the ter-alkyl group) have been prepared and examined as borane carriers. The complexing ability of these N,N-diethyl-tert-alkylamines with borane decreases in the order: t-BuNEt2 > t-PentNEt2 > t-HeptNEt2 > t-HexNEt2 ≥ t-OctNEt2. From these preliminary studies, the more promising tert-octyldialkylamines were selected for detailed studies. The optimum steric bulk around the nitrogen atom was established by comparing various tert-octyldialkylamines containing variable steric requirements for both the alkyl groups. The complexing ability of these amines with borane decreases in the order shown: t-OctNMe2 (5) > t-OctNEtMe (6) > t-OctN-(CH2CH2)2O (7) > t-OctNEt2 (4) > t-OctNBuiMe (8) > t-OctNPrn2 (9). The reactivity of the corresponding borane adducts toward 1-octene increases in the reverse order. Among the various tert-octyldialkylamine-boranes prepared and examined, only t-OctNEt2 (4) forms a highly reactive liquid borane adduct, which hydroborates 1-octene in tetrahydrofuran rapidly at room temperature. Accordingly, detailed hydroboration studies with this new, highly reactive amine-borane adduct, t-OctEt2N:BH3 (10) and representative mono-, di-, tri-, and tetra-substituted olefins were carried out at room temperature (22 ± 3°C) in selected solvents, tetrahydrofuran, dioxane, tert-butyl methyl ether, n-pentane and dichloromethane. Simple unhindered olefins were hydroborated to the trialkylborane stage, whereas hindered olefins were partially hydroborated to the mono or dialkylborane stage. The hydroborations can be carried out conveniently in a variety of solvents. The amine-borane adduct showed enhanced reactivity in dioxane but low reactivity in dichloromethane. The alkylboranes obtained after hydroboration were oxidized with hydrogen peroxide/ sodium hydroxide and the product alcohols were obtained in quantitative yields, as established by GC analysis. The carrier amine was recovered by simple acid-base manipulations in good yield and can be readily recycled back to the borane adduct.
