13326-10-8Relevant articles and documents
Indium-catalyzed reaction for the synthesis of carbamates and carbonates: selective protection of amino groups
Kim, Joong-Gon,Jang, Doo Ok
, p. 2688 - 2692 (2009)
We developed a simple, efficient, and selective method for preparing organic carbamates and carbonates using a catalytic amount of indium. A wide range of carbamates and carbonates were synthesized in high yields. The method is also applicable to the selective protection of amino groups under mild conditions.
A safe and mild synthesis of organic carbonates from alkyl halides and tetrabutylammonium alkyl carbonates
Verdecchia, Mirella,Feroci, Marta,Palombi, Laura,Rossi, Leucio
, p. 8287 - 8289 (2002)
A safe and mild procedure for the synthesis of mixed organic carbonates is described. Reaction of commercially available tetrabutylammonium methoxide and ethoxide with carbon dioxide yields the corresponding methyl and ethyl tetrabutylammonium carbonates (TBAMC and TBAEC). The reactions of these new compounds with several different alkyl halides give methyl and ethyl carbonates in high yields. The use of classic toxic and harmful chemicals such as phosgene and carbon monoxide is avoided.
Investigation of dialkyltin compounds as catalysts for the synthesis of dialkyl carbonates from alkyl carbamates
Suciu, Elena N.,Kuhlmann, Barbara,A. Knudsen, George,Michaelson, Robert C.
, p. 41 - 54 (1998)
New syntheses for dibutyldimethoxytin, dibutyldiisocyanatotin and 1,1,3,3-tetrabutyl-1,3-diisocyanatodistannoxane as well as the novel compounds dibutylisocyanatomethoxytin and 1,1,3,3-tetrabutyl-1-methoxy-3-isocyanatodistannoxane are described. These com
TBD catalysis with dimethyl carbonate: A fruitful and sustainable alliance
Mutlu, Hatice,Ruiz, Johal,Solleder, Susanne C.,Meier, Michael A. R.
, p. 1728 - 1735 (2012)
This work presents the synthesis of unsymmetric and symmetric organic carbonates as well as the synthesis of polycarbonates in an efficient and sustainable approach. All reactions were carried out at atmospheric pressure at 80°C and the use of classic toxic and harmful chemicals, such as phosgene and carbon monoxide, was avoided. The key finding of this manuscript is that the use of 1,5,7-triazabicyclo[4.4.0]dec-5-ene, TBD, an organocatalyst, in combination with dimethyl carbonate (DMC), a non-toxic and renewable starting material, allows the synthesis of the mentioned unsymmetric carbonates in yields of up to 98% under optimized conditions. The structure of the alcohols used for this approach was found to influence the DMC-ROH ratio required to maximize the yield of the desired structure. Finally, the results obtained for the synthesis of low molecular weight building blocks could be transferred to the catalytic synthesis of high molecular weight polycarbonates. The Royal Society of Chemistry.
Discovery and Design of Family VIII Carboxylesterases as Highly Efficient Acyltransferases
Müller, Henrik,Godehard, Simon P.,Palm, Gottfried J.,Berndt, Leona,Badenhorst, Christoffel P. S.,Becker, Ann-Kristin,Lammers, Michael,Bornscheuer, Uwe T.
supporting information, p. 2013 - 2017 (2020/11/30)
Promiscuous acyltransferase activity is the ability of certain hydrolases to preferentially catalyze acyl transfer over hydrolysis, even in bulk water. However, poor enantioselectivity, low transfer efficiency, significant product hydrolysis, and limited substrate scope represent considerable drawbacks for their application. By activity-based screening of several hydrolases, we identified the family VIII carboxylesterase, EstCE1, as an unprecedentedly efficient acyltransferase. EstCE1 catalyzes the irreversible amidation and carbamoylation of amines in water, which enabled the synthesis of the drug moclobemide from methyl 4-chlorobenzoate and 4-(2-aminoethyl)morpholine (ca. 20 % conversion). We solved the crystal structure of EstCE1 and detailed structure–function analysis revealed a three-amino acid motif important for promiscuous acyltransferase activity. Introducing this motif into an esterase without acetyltransferase activity transformed a “hydrolase” into an “acyltransferase”.
One-pot carbonyl reduction and carbonate formation using sodium borohydride in dialkyl carbonate solvents
Osumah, Abdulakeem,Magolan, Jakob,Waynant, Kristopher V.
supporting information, (2019/10/14)
Preparation of mixed carbonates proceeded in one step from ketones and aldehydes via treatment with NaBH4 in dimethyl or diethyl carbonate solvent at elevated temperatures. This is an efficient and convenient alternative to the traditional two-step sequence of carbonyl reduction to alcohol and subsequent carbonate formation by treatment with an alkyl chloroformate. 25 examples are presented from 49 to 92% yield, highlighting the versatility of this reaction.