- Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source
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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.
- Yano De Albuquerque, Danilo,Teixeira, Wystan K. O.,Sacramento, Manoela Do,Alves, Diego,Santi, Claudio,Schwab, Ricardo S.
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supporting information
p. 595 - 605
(2022/01/12)
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- Synthesis of selenol esters via the reaction of acyl chlorides with diselenides in the presence of Zn dust catalyzed by CoCl2·6H2O
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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
- Dall'Oglio, Evandro L.,Stein, André L.,Vasconcelos, Leonardo G.,Vieira, Lucas C. C.,de Oliveira, Angélica J.,de Oliveira, Sandynara A.
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supporting information
(2021/08/25)
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- Nickel-Catalyzed Intramolecular Decarbonylative Coupling of Aryl Selenol Esters
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This report describes a method for Ni-catalyzed intramolecular decarbonylative coupling, which enables the conversion of areneselenol esters to diaryl selenides. The inexpensive and readily available catalyst can be employed under mild reaction conditions for the construction of structurally diverse diaryl selenides, including heterocyclic and natural product derivatives. (Figure presented.).
- Bai, Jin-Hua,Qi, Xiu-Juan,Sun, Wei,Yu, Tian-Yang,Xu, Peng-Fei
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supporting information
p. 2084 - 2088
(2021/03/01)
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- Iron(III)-catalyzed synthesis of selenoesters from α-amino carbonyl derivatives at room temperature
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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.
- Chatterjee, Rana,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Majee, Adinath
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- Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions
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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.
- He, Chunhuan,Qian, Xuewei,Sun, Peipei
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supporting information
p. 6072 - 6075
(2014/08/05)
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- Acylation of diselenides and disulfides with N-acylbenzotriazoles promoted by SmI2
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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.
- Tu, Ya Wei,Zhou, Lie Jin,Lv, Xin,Wang, Xiao Xia
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p. 435 - 439
(2014/05/06)
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- Investigation on the se-acylation with N-acylbenzotriazoles
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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
- Jiang, Junyan,Wang, Wencun,Wang, Xiaoxia,Zhu, Xiangming,Li, Zhifang
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experimental part
p. 2047 - 2054
(2011/12/01)
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- Organoselenosilane-mediated selective mild access to selenolesters, selenoanhydrides and diacyl diselenides
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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
- Capperucci, Antonella,Deglinnocenti, Alessandro,Tiberi, Caterina
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experimental part
p. 2248 - 2252
(2011/10/31)
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- A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite
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Rongalite promotes cleavage of diaryl disulfides generating chalcogenolate anions that then undergo facile acylation with anhydrides in the presence of CsF to afford thioesters (3) with good to excellent yields. By using the present protocol, 5-arylthio-5-oxopentanoic acid (4) can be facilely prepared. The important features of the methodology are broad substrate scope, simple operation, and no requirement for metal catalysts. It is noteworthy that acylations of diphenyl diselane with anhydrides are also conducted smoothly to afford selenoesters (5) in good yields under the standard conditions.
- Dan, Weixing,Deng, Hongjuan,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Wu, Huayue
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experimental part
p. 7384 - 7388
(2010/10/02)
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- Ionic liquid: An efficient and reusable media for seleno- and thioester synthesis promoted by indium
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A series of thio and selenoesters were efficiently obtained employing stable diorganyl chalcogenides, acyl chlorides, and In as reducing agent in BMIM·PF6. Recycling of the ionic liquid was also performed, which was reused three times.
- Tabarelli, Greice,Alberto, Eduardo E.,Deobald, Anna M.,Marin, Graciane,Rodrigues, Oscar E.D.,Dornelles, Luciano,Braga, Antonio L.
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experimental part
p. 5728 - 5731
(2010/11/16)
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- Iron-catalyzed synthesis of selenoesters from diselenides and acyl chlorides or acid anhydrides in the presence of magnesium dust
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A novel and efficient synthetic methodology for the iron-catalyzed preparation of selenoesters by the reaction of diselenides with acyl chlorides or acid anhydrides has been developed. In the presence of magnesium dust, iron catalyzes the cleavage of the
- Ren, Kai,Wang, Min,Liu, Ping,Wang, Lei
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experimental part
p. 1078 - 1082
(2010/05/18)
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- Synthesis of Selenol Esters from Acid Chlorides and Organic Diselenides in the Presence of the Zn/AlCl3 System
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Treatment of diphenyl and dibenzyl diselenides with aliphatic and aromatic acid chlorides in the presence of Zn/AlCl3 affords selenol esters. Availability, low costs, and lack of toxicity of the catalysts, simple reaction work-up, and high yiel
- Movassagh, Barahman,Mirshojaei, Fatemeh
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p. 831 - 835
(2007/10/03)
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- Reductive cleavage of the Se-Se bond in diselenides by the CeCl 3/Sm system: A novel method for the synthesis of selenoesters
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Treatment of diaryl diselenides 1 with cerium trichloride and metallic samarium in tetrahydrofuran conveniently gives samarium aryl selenolates, the "living" species which react with acid chlorides and acid anhydrides to afford sclenoesters 2 in good yiel
- Li, Xue,Zhang, Songlin,Wang, Yulu,Zhang, Yongmin
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p. 2000 - 2002
(2007/10/03)
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- Phenyl tributylstannyl selenide as a promising reagent for introducion of the phenylseleno group
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A new synthetic method of organoselenium compounds has been developed. When phenyl tributylstannyl selenide (PhSeSnBu3) was allowed to react with acyl or aroyl chlorides in the presence of a catalytic amount of a palladium complex such as Pd(PPh3)4, Se-phenyl selenol esters were obtained in moderate to good yields. Similarly, the palladium complex catalyzed the reaction of PhSeSnBu3 with α-halo carbonyl compounds to afford the corresponding α-phenyseleno carbonyl compounds in moderate yields.
- Nishiyama, Yutaka,Kawamatsu, Hiroaki,Funato, Saori,Tokunaga, Keiji,Sonoda, Noboru
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p. 3599 - 3602
(2007/10/03)
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- Synthesis of selenol esters: Palladium-catalyzed coupling of phenyl tributylstannyl selenide with aryl iodides and carbon monoxide
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It was found that palladium complex catalyzed three-component coupling of phenyl tributylstannyl selenide with aryl iodides and carbon monoxide to afford the corresponding selenol esters in moderate to good yields.
- Nishiyama, Yutaka,Tokunaga, Keiji,Kawamatsu, Hiroaki,Sonoda, Noboru
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p. 1507 - 1509
(2007/10/03)
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- Tributylstannyl aryl selenides as efficient arylselenating agents in the synthesis of seleno esters
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Tributyltin aryl selenides are convenient and highly efficient arylselenating agents in reactions with acyl chlorides. The activity of acetic anhydride is considerably lower but it can be involved into the arylselenation reaction in the presence of PdCls
- Beletskaya,Sigeev,Peregudov,Petrovskii
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p. 1703 - 1709
(2007/10/03)
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- Water accelerated Sm/TMSC1 reductive cleavage of the Se-Se bond: Synthesis of selenoesters and selenoformates
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The reduction of diselenides by the Sm/TMSC1/H2O system led to selenide anions. These 'living' species reacted smoothly with acid chlorides, acid anhydrides and methyl chloroformate respectively to afford the desired selenoesters and selenoform
- Wang, Lei,Zhang, Yongmin
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p. 3107 - 3115
(2007/10/03)
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- A Convenient Preparation of Aryl Arylcarbonyl Diselenides
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A novel method for the synthesis of aryl arylcarbonyl diselenides via the reaction of potassium areneselenocarboxylates with areneselenenyl bromides is described.
- Ishihara, Hideharu,Matsunami, Nobuaki,Yamada, Yukihiro
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p. 371 - 373
(2007/10/02)
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