23522-73-8Relevant articles and documents
Environmentally benign decarboxylative: N-, O-, and S-Acetylations and acylations
Ghosh, Santanu,Purkait, Anisha,Jana, Chandan K.
supporting information, p. 8721 - 8727 (2020/12/30)
An operationally simple and general method for acetylation and acylation of a wide variety of substrates (amines, alcohols, phenols, thiols, and hydrazones) has been reported. Meldrum's acid and its derivatives have been used as an air-stable, non-volatile, cost-effective, and easy to handle acetylating/acylating agent. Easily separable byproducts (CO2 and acetone) allowed the isolation of analytically pure acetylated products without the requirement of work-up and any chromatography. This journal is
Fe-catalyzed thioesterification of carboxylic esters
Magens, Silja,Plietker, Bernd
scheme or table, p. 8807 - 8809 (2011/09/16)
Second nature: Starting from shelf-stable aryl esters and thiols, a variety of carboxylic acid esters were transformed into the corresponding thioesters with no racemization of labile stereocenters (see scheme). The method was successfully applied in a native chemical-ligation-type peptide formation, which suggests that the thiol may act as a co-catalyst for future 1,2-additions of pronucleophiles to carboxylic esters.
Reaction of dicarbonates with carboxylic acids catalyzed by weak Lewis acids: General method for the synthesis of anhydrides and esters
Bartoli, Giuseppe,Bosco, Marcella,Carlone, Armando,Dalpozzo, Renato,Marcantoni, Enrico,Melchiorre, Paolo,Sambri, Letizia
, p. 3489 - 3496 (2008/09/19)
The reaction between carboxylic acids (RCOOH) and dialkyl dicarbonates [(R1OCO)2O], in the presence of a weak Lewis acid such as magnesium chloride and the corresponding alcohol (R1OH) as the solvent, leads to the esters RCOOR1 in excellent yields. The mechanism involves a double addition of the acid to the dicarbonate, affording a carboxylic anhydride [(RCO)2O], R1OH and carbon dioxide. The esters arise from the attack of the alcohols on the anhydrides. Exploiting the lesser reactivity of tert-butyl alcohol in comparison with other alcohols, a clean synthesis of both carboxylic anhydrides and esters has been set up. In the former reaction, an acid/Boc2O molecular ratio of 2:1 leads to the anhydride in good to excellent yields, depending on the stability of the resulting anhydride to the usual workup conditions. In the latter reaction, stoichiometric mixtures of the acid and Boc2O are allowed to react with a twofold excess of a primary alcohol, secondary alcohol or phenol (R 2OH) to give the corresponding esters (RCOOR2). Purification of the products is particularly easy since all byproducts are volatile or water soluble. A very easy chromatography is required only in the case of nonvolatile alcohols. A broad variety of sensitive functional groups is tolerated on both the acid and the alcohol, in particular a high chemoselectivity is observed. In fact, no transesterification processes occur with the acid-sensitive acetoxy group and methyl esters. Georg Thieme Verlag Stuttgart.
