77750-08-4Relevant academic research and scientific papers
Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source
Yano De Albuquerque, Danilo,Teixeira, Wystan K. O.,Sacramento, Manoela Do,Alves, Diego,Santi, Claudio,Schwab, Ricardo S.
supporting information, p. 595 - 605 (2022/01/12)
A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, low-cost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access to a large family of selenoesters in high yields (up to 97%) while operating under mild reaction conditions, and avoids the use of selenol which is difficult to manipulate, easily oxidizes, and has a bad odor. Additionally, this method can be efficiently extended to the synthesis of thioesters with moderate-to-excellent yields, by employing for the first time diorganyl disulfides as precursors.
Synthesis of selenol esters via the reaction of acyl chlorides with diselenides in the presence of Zn dust catalyzed by CoCl2·6H2O
Dall'Oglio, Evandro L.,Stein, André L.,Vasconcelos, Leonardo G.,Vieira, Lucas C. C.,de Oliveira, Angélica J.,de Oliveira, Sandynara A.
supporting information, (2021/08/25)
A practical and efficient approach for the synthesis of selenol and thiol esters is described via the reaction of acyl chlorides with diselenides or disulfides in the presence of Zn dust catalyzed by inexpensive CoCl2·6H2O This proto
Green synthesis and antibacterial activity of chalcogenoesters
Baldisserotto, Bernardo,Dornelles, Luciano,Junior, Guerino B.,Ravanello, Bruno B.,Rodrigues, Oscar E. D.,Santos, Roberto C. V.,Soares, Letiére C.,da Rosa, Fernanda H.,da Silva, Rafael S.,de A. Vaucher, Rodrigo,dos S. Barboza, Victor
, (2020/03/31)
Abstract: Herein, we present a new variation for an eco-friendly methodology for the synthesis of chalcogenoester in good-to-excellent yields in a short time, with an easy work-up/purification step, and in a greenest methodology, affording the minimum gen
Iron(III)-catalyzed synthesis of selenoesters from α-amino carbonyl derivatives at room temperature
Chatterjee, Rana,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Majee, Adinath
, (2019/09/30)
An Fe(III)-catalyzed efficient method has been developed for the synthesis of selenoester derivatives in high yields through the coupling of α-amino carbonyl/glycine derivatives and diselenides under ambient air. A library of benzoselenoate derivatives having a variety of substituents has been synthesized. A plausible reaction pathway has been predicted. Experimental results suggest that the reaction proceeds through a radical pathway. Operational simplicity, compatibility with various α-amino carbonyls and diselenides, high yields, fast reaction and mild reaction conditions are the notable advantages of this procedure. We have also shown the practical application of the synthesized selenoesters which is useful to generate peptide bonds in biological sciences.
Acylation of diselenides and disulfides with N-acylbenzotriazoles promoted by SmI2
Tu, Ya Wei,Zhou, Lie Jin,Lv, Xin,Wang, Xiao Xia
, p. 435 - 439 (2014/05/06)
The acylation of diselenides or disulfides with N-acylbenzotriazoles mediated by SmI2 has been achieved successfully without the presence of HMPA, and the corresponding selenolesters or thioesters have been prepared in good yields.
Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions
He, Chunhuan,Qian, Xuewei,Sun, Peipei
supporting information, p. 6072 - 6075 (2014/08/05)
Thiol and selenol esters were synthesized by a direct oxidative coupling reaction of aldehydes with disulfides or diselenides in ethyl acetate under metal-free conditions. Among the oxidants examined, tert-butyl peroxide (TBP) was shown to give the best results. For the substrates with both electron-donating and electron-withdrawing substituents, the reaction proceeded smoothly and gave moderate to good yields. Compared with the previous method, the present route is very simple, atom-economical and environmentally friendly. This journal is the Partner Organisations 2014.
Synthesis of selenol esters from diorganyl diselenides and acyl chlorides under solvent-free conditions and microwave irradiation
Godoi, Marcelo,Ricardo, Eduardo W.,Botteselle, Giancarlo V.,Galetto, Fabio Z.,Azeredo, Juliano B.,Braga, Antonio L.
supporting information; experimental part, p. 456 - 460 (2012/03/26)
Herein, we report an efficient, quick and eco-friendly new method for the synthesis of a variety of selenol esters. This novel solvent-free methodology gave good to excellent isolated yields of desired products after just 2 min under microwave irradiation
Investigation on the se-acylation with N-acylbenzotriazoles
Jiang, Junyan,Wang, Wencun,Wang, Xiaoxia,Zhu, Xiangming,Li, Zhifang
experimental part, p. 2047 - 2054 (2011/12/01)
The acylation of Se-nucleophiles with N-acylbenzotriazoles was investigated. Samarium phenylselenolate and benzylselenolate (RSeSmI 2) reacted with N-aroyl and N-alkanoylbenzotriazoles smoothly and afforded the corresponding selenol esters in g
Aryl(trimethylsilyl)selenides as reagents for the synthesis of mono- and diselenoesters
Taher, Deeb,Corrigan, John F.
experimental part, p. 5943 - 5952 (2012/01/04)
Silylated organoselenium reagents react undermild conditions with acid chlorides to provide a high yield route to aromatic selenoesters. The synthesis, structures, and spectroscopic properties of the selenoesters C 6H5SeC(O)R(R=CH2CH3, 1; p-CH 3C6H4, 2; p-C6Me4Br, 3; p-C6Me4C-(O)SeC 6H5, 4) and RC(O)SeFcSeC(O)R (Fc = Fe(C5H4)2;R=CH 2CH3, 5; p-CH3C6H4, 6; p-BrC6Me4, 7) and RC(O)Se(C6H4)nSeC(O)R (n = 1, R=CH2CH3, 8a; n = 2, R =CH2CH3, 8b; n = 1, R= p-CH3C 6H4, 9a; n = 2, R=p-CH3C6H 4, 9b; n=1,R=p-C6Me4Br, 10a; n=2, R = p-C6Me4Br, 10b) andC 6H5SeC(O)CH2CH2C(O)SeC 6H5 11 are discussed. Although 11 can be prepared in high yield from the reaction of C6H5SeSiMe3 and ClC(O)CH 2CH2C(O)Cl in tetrahydrofuran solvent, similar reactions in the absence of solvent led to the competitive formation of both 11 and (C6H5Se)3CCH2CH2C(O)OSiMe3 12. The new selenoesters have been characterized by multinuclear NMR (1H, 13C, 77Se), IR, and UV-vis spectroscopies, electrospray mass spectrometry, and, for complexes 2, 4, 7, 10b, and 12, single-crystal X-ray diffraction. 2011 American Chemical Society.
Organoselenosilane-mediated selective mild access to selenolesters, selenoanhydrides and diacyl diselenides
Capperucci, Antonella,Deglinnocenti, Alessandro,Tiberi, Caterina
experimental part, p. 2248 - 2252 (2011/10/31)
Reaction of acyl chlorides with phenylselenotrimethyl-silane promoted by TBAF afforded a mild general access to selenolesters in good yields. When acyl chlorides were reacted with bis(trimethylsilyl)selenide (HMDSS) in 2:1 or 1:1 ratio a selective entry t
