7155-12-6Relevant articles and documents
Mechanistic elucidation of monoalkyltin(iv)-catalyzed esterification
Hermans, Joen J.,Korstanje, Ties J.,Reek, Joost N. H.,Tromp, Moniek,Wolzak, Lukas A.,de Vries, Folkert,van den Berg, Keimpe J.
, p. 3326 - 3332 (2021)
Monoalkyltin(iv) complexes are well-known catalysts for esterification reactions and polyester formation, yet the mode of operation of these Lewis acidic complexes is still unknown. Here, we report on mechanistic studies ofn-butylstannoic acid in stoichiometric and catalytic reactions, analyzed by NMR, IR and MS techniques. While the chemistry ofn-butyltin(iv) carboxylates is dominated by formation of multinuclear tin assemblies, we found that under catalytically relevant conditions only monomericn-BuSn(OAc)3and dimeric (n-BuSnOAc2OEt)2are present. Density functional theory (DFT) calculations provide support for a mononuclear mechanism, wheren-BuSn(OAc)3and dimeric (n-BuSnOAc2OEt)2are regarded as off-cycle species, and suggest that carbon-oxygen bond breaking is the rate-determining step.
Electrochemical esterification via oxidative coupling of aldehydes and alcohols
Smeyne, Dylan,Verboom, Katherine,Bryan, Maria,LoBue, James,Shaikh, Abid
supporting information, (2021/03/26)
An electrolytic method for the direct oxidative coupling of aldehydes with alcohols to produce esters is described. Our method involves anodic oxidation in presence of TBAF as supporting electrolyte in an undivided electrochemical cell equipped with graphite electrodes. This method successfully couples a wide range of alcohols to benzaldehydes with yields ranging from 70 to 90%. The protocol is easy to perform at a constant voltage conditions and offers a sustainable alternative over conventional methods.
Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids Using α,α-Dichlorodiphenylmethane
Lee, Chang-Hee,Lee, Soo-Min,Min, Byul-Hana,Kim, Dong-Su,Jun, Chul-Ho
, p. 2468 - 2471 (2018/04/25)
A new method for chlorination of alcohols and carboxylic acids, using α,α-dichlorodiphenylmethane as the chlorinating agent and FeCl3 as the catalyst, was developed. The method enables conversions of various alcohols and carboxylic acids to their corresponding alkyl and acyl chlorides in high yields under mild conditions. Particulary interesting is the observation that the respective alkyl bromides and iodides can be generated from alcohols when either LiBr or LiI are present in the reaction mixtures.