6324-79-4Relevant academic research and scientific papers
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.
Highly selective primary alkoxycarboxylation and esterification of unprotected pyranose derivatives mediated by scandium(III) triflate catalysis
McClure, Michael S.,Berry, Malcolm B.,Caine, Darren,Crawford, Claire,Crump, Brian C.,Glover, Bobby N.,Kedia, Sandeep B.,Millar, Alan,Mitchell, Mark B.,Nichols, Christopher J.,Patterson, Daniel E.,Powers, Jeremiah
scheme or table, p. 3561 - 3565 (2012/07/27)
A highly selective method for the alkoxycarboxylation and acylation of primary alcohols of pyranose derivatives is described. The reaction is high yielding and proceeds under mild conditions with 0.15-1 mol-% Sc(OTf) 3 used in combination with anhydrides or pyrocarbonates at 40-50 °C. Selectivities observed for alkoxycarboxylation of unprotected pyranose derivatives are > 95 and this constitutes a significant advantage over existing methods. Mechanistic implications, including the role of steric demand and metal-heteroatom coordination are also discussed.
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 (2007/10/03)
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.
Electrogenerated base-promoted synthesis of organic carbonates from alcohols and carbon dioxide
Casadei, Maria Antonietta,Cesa, Stefania,Rossi, Leucio
, p. 2445 - 2448 (2007/10/03)
Electrogenerated bases promote the reaction between primary alcohols and carbon dioxide to give organic carbonates in excellent yields. Secondary alcohols are converted in moderate yields, whereas tertiary alcohols and phenols are unreactive. 1,2-Diols give a mixture of both cyclic and linear diand monocarbonates. These latter are intermediates in the reaction pathway leading to the cyclic derivatives.
Electrochemical activation of carbon dioxide: Synthesis of organic carbonates
Casadei, M. Antonietta,Inesi, Achille,Rossi, Leucio
, p. 3565 - 3568 (2007/10/03)
Electrochemically activated CO2 reacts, under mild conditions, with primary and secondary alcohols bearing a leaving group at the α-position affording the corresponding cyclic carbonates in high yields; unsubstituted alcohols are converted, after addition of EtI, into the corresponding unsymmetrical ethyl carbonates in moderate to good yields. Tertiary alcohols and phenols are stable to the reagent.
