111-86-4Relevant articles and documents
Cs2CO3-promoted efficient carbonate and carbamate synthesis on solid phase
Salvatore, Ralph N.,Flanders, Vincent L.,Ha, Dang,Jung, Kyung Woon
, p. 2797 - 2800 (2000)
Mild and efficient preparation of alkyl carbonates and carbamates on solid supports is described herein. Alcohols or amines were coupled with Merrifield's resin through a CO2 linker in the presence of cesium carbonate and tetrabutylammonium iodide (TBAI).
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Ralston
, (1940)
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Direct terminal alkylamino-functionalization via multistep biocatalysis in one recombinant whole-cell catalyst
Schrewe, Manfred,Ladkau, Nadine,Buehler, Bruno,Schmid, Andreas
, p. 1693 - 1697 (2013)
Direct and regiospecific amino-functionalization of non-activated carbon could be achieved using one recombinant microbial catalyst. The presented proof of concept shows that heterologous pathway engineering allowed the construction of a whole-cell biocatalyst catalyzing the terminal amino-functionalization of fatty acid methyl esters (e.g., dodecanoic acid methyl ester) and alkanes (e.g., octane). By coupling oxygenase and transaminase catalysis in vivo, both substrates are converted with absolute regiospecificity to the terminal amine via two sequential oxidation reactions followed by an amination step. Such demanding chemical three-step reactions achieved with a single catalyst demonstrate the tremendous potential of whole-cell biocatalysts for the production of industrially relevant building blocks. Copyright
Kinetic studies of the Hydrolysis of n-Octylamine on the Surface of a Sodium Dodecyl Sulfate Micelle by the Ultrasonic Absorption Method
Yamashita, Teruyo,Yano, Hiroshige,Harada, Shoji,Yasunaga, Tatsuya
, p. 5482 - 5485 (1983)
Ultrasonic relaxation absorption has been observed in aqueous solution of n-octylamine (OA) in the presence of micelles of sodium dodecyl sulfate (SDS).From various experiments changing (i) the concentrations of OA and SDS, (ii) the alkyl-chain length of the detergent and amine, (iii) the pH of the solution, and (iv) the type of detergent, the relaxation absorption has been ascribed to the hydrolysis of OA on the surface of the SDS micelle: C8H17NH3+ + OH- C8H17NH2 + H2O.The forward (kf) and backward (kb) rate constants, the apparent equilibrium constant (K), and the volume change (ΔV) for the hydrolysis have been determined to be γ2kf = 5.5*108 M-1 s-1, kb = 1.2*107 s-1, K (=γ2kf/kb) = 45 M-1, and ΔV = 26.5 cm3 mol-1 at 20 deg C, respectively, where γ is the mean ionic activity coefficient.The values of γ2kf and K were found to be smaller than the corresponding values in the absence of the micelle by a factor of about 1/50.These micellar effects have been interpreted in terms of electrostatic interactions between the micelle and OH- and OA+ ions.
Catalytic Hydrogenation of Urea Derivatives and Polyureas
Kumar, Amit,Luk, James
supporting information, p. 4546 - 4550 (2021/08/30)
We present herein the catalytic hydrogenation of various urea derivatives to amines and methanol. The reaction is catalyzed by a ruthenium or an iridium Macho pincer complex and produces amine and methanol in very good to excellent yields. Moreover, we also expand this concept to demonstrate the first example of the hydrogenative depolymerization of polyureas to produce diamines and methanol in moderate yields.
Hydroboration of Nitriles, Esters, and Carbonates Catalyzed by Simple Earth-Abundant Metal Triflate Salts
Thenarukandiyil, Ranjeesh,Satheesh, Vanaparthi,Shimon, Linda J. W.,de Ruiter, Graham
, p. 999 - 1006 (2021/03/30)
During the past decade earth-abundant metals have become increasingly important in homogeneous catalysis. One of the reactions in which earth-abundant metals have found important applications is the hydroboration of unsaturated C?C and C?X bonds (X=O or N). Within these set of transformations, the hydroboration of challenging substrates such as nitriles, carbonates and esters still remain difficult and often relies on elaborate ligand designs and highly reactive catalysts (e. g., metal alkyls/hydrides). Here we report an effective methodology for the hydroboration of challenging C≡N and C=O bonds that is simple and applicable to a wide set of substrates. The methodology is based on using a manganese(II) triflate salt that, in combination with commercially available potassium tert-butoxide and pinacolborane, catalyzes the hydroboration of nitriles, carbonates, and esters at room temperature and with near quantitative yields in less than three hours. Additional studies demonstrated that other earth-abundant metal triflate salts can facilitate this reaction as well, which is further discussed in this report.
