An approach to the synthesis of thioesters and selenoesters promoted by Rongalite®

Abstract

Rongalite® promove a clivagem de diarildissulfetos gerando os calcogenolatos correspondentes, que reagem facilmente com N-acilbenzotriazóis na presença de K 2 CO 3 , produzindo tioésteres em bons a excelentes rendimentos. As principais características desta metodologia são a não necessidade de catalisdores metálicos ou de reagentes caros e o alto rendimento. É digno de nota que as reações de disseleneto de difenila com N-acilbenzotriazóis são também conduzidas para produzir selenoésteres em bons rendimentos sob condições normais. Rongalite® promotes cleavage of diaryldisulfides generating the corresponding chalcogenolate anions that then undergo facile reaction with N-acylbenzotriazoles in the presence of K 2 CO 3 to afford thioesters in good to excellent yields. The important features of this methodology are no requirement of metal catalysts, without any expensive reagent and high yields. It is noteworthy that the reactions of diphenyl diselenide with N-acylbenzotriazoles are also conducted to afford selenoesters in good yields under the standard conditions.

Atom Efficient Preparation of Zinc Selenates for the Synthesis of Selenol Esters under “On Water” Conditions

“…As a consequence of the increasing demand for selenol esters, the number of methods to prepare this class of compounds has been increased along the years [1,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43] Among the strategies to prepare selenol esters there are the reactions of nucleophilic selenium reagents with an acyl group source, such as N -acyl benzotriazoles [17,18] activated carboxylic acids (using DCC [3] or PBu 3 [4,5,19,20]), enol esters [21], anhydrides [22,23,24], esters [25], carbon monoxide [26,27], aldehydes [28,29] or acyl chlorides [2,7,30,31,32,33,34,35,36,37,38,39,40,41,42,43]. Other approaches to selenol esters involve the alkylation of selenocarboxylate anions with alkyl h...…”

Rongalite

“…For example, rongalite is capable of producing the perfluoroalkyl free radicals via dehalogenation of alkyl halides, [2][3][4] such as direct perfluoroalkylation of pyridines, 5 coumarins 6 and 2-quinolones. 7 It has been also used for the cleavage of diaryl disuldes and dise-lenides generating the corresponding chalcogenolate species in situ that then undergo facile ring opening and acylation, affording b-hydroxy sulfides, 8 thioesters and selenoesters, 9 respectively. It was also found to be a sulfoxylate dianion equivalent in the conversion of dihalides into sultine derivatives.…”