- 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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Read Online
- Photoredox-Enabled Chromium-Catalyzed Alkene Diacylations
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Transition-metal-catalyzed cross-coupling reactions are a powerful tool to construct carbon-carbon bonds in modern synthetic chemistry. Chromium catalysis is much less developed compared with the widely used palladium and nickel catalysis. Herein, we repo
- Cheng, Ying,Jin, Weiwei,Liu, Jing,Lu, Liang-Qiu,Luo, Yixin,Qi, Xiaotian,Sun, Peng-Chao,Xiao, Wen-Jing,Zhao, Wei
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p. 1879 - 1885
(2022/02/07)
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- 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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- P-Silylation of Arenes via Organic Photoredox Catalysis: Use of p-Silylated Arenes for Exclusive o-Silylation, o-Acylation, and o-Alkylation Reactions
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Photocatalytic regiospecific p-silylation of arenes has been achieved by the coupling of in situ generated silyl radical with arene radical cation. The strategy involves reductive activation of PhSe-SiR3 and single electron transfer from the electron rich
- Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Pushpendra,Mondal, Pradip Kumar
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supporting information
p. 7730 - 7734
(2021/10/25)
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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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- Thioesterification and Selenoesterification of Amides via Selective N-C Cleavage at Room Temperature: N-C(O) to S/Se-C(O) Interconversion
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The direct nucleophilic addition to amides represents an attractive methodology in organic synthesis that tackles amidic resonance by ground-state destabilization. This approach has been recently accomplished with carbon, nitrogen and oxygen nucleophiles.
- Li, Guangchen,Rahman, Md. Mahbubur,Szostak, Michal
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supporting information
p. 1060 - 1066
(2020/04/01)
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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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- General, Mild, and Metal-Free Synthesis of Phenyl Selenoesters from Anhydrides and Their Use in Peptide Synthesis
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A mild, practical, and simple procedure for phenyl selenoesters synthesis from several anhydrides and diphenyl diselenide was developed. This transition-metal-free method provides a straightforward entry to storable Fmoc-amino acid selenoesters which are effective chemoselective acylating reagents. An application to oligopeptide synthesis was illustrated.
- Temperini, Andrea,Piazzolla, Francesca,Minuti, Lucio,Curini, Massimo,Siciliano, Carlo
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p. 4588 - 4603
(2017/05/12)
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- P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis
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p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.
- Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Bhawana,Vanka, Kumar,Jain, Shailja
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supporting information
p. 12337 - 12340
(2017/11/20)
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- Atom efficient preparation of zinc selenates for the synthesis of selenol esters under “On Water” conditions
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We describe here an atom efficient procedure to prepare selenol esters in good to excellent yields by reacting [(PhSe)2Zn] or [(PhSe)2Zn]TMEDA with acyl chlorides under “on water” conditions. The method is applicable to a series of aromatic and aliphatic acyl chlorides and tolerates the presence of other functionalities in the starting material.
- Sancineto, Luca,Vargas, Jaqueline Pinto,Monti, Bonifacio,Arca, Massimiliano,Lippolis, Vito,Perin, Gelson,Lenardao, Eder Joao,Santi, Claudio
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- Reaction of Acyl Chlorides with in Situ Formed Zinc Selenolates: Synthesis of Selenoesters versus Ring-Opening Reaction of Tetrahydrofuran
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Attempting to apply the in situ production of PhSeZnSePh to the synthesis of selenoesters, an unexpected reaction involving the solvent (tetrahydrofuran) was observed and studied. We reported here some evidences about the mechanism and the possibility to
- Bellino, Gemma,Scisciani, Marialaura,Vargas, Jaqueline Pinto,Sancineto, Luca,Bagnoli, Luana,Marini, Francesca,Lüdtke, Diogo Seibert,Lenardao, Eder Joao,Santi, Claudio
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- Aldehyde capture ligation for synthesis of native peptide bonds
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Chemoselective reactions for amide bond formation have transformed the ability to access synthetic proteins and other bioconjugates through ligation of fragments. In these ligations, amide bond formation is accelerated by transient enforcement of an intramolecular reaction between the carboxyl and the amine termini of two fragments. Building on this principle, we introduce an aldehyde capture ligation that parlays the high chemoselective reactivity of aldehydes and amines to enforce amide bond formation between amino acid residues and peptides that are difficult to ligate by existing technologies.
- Raj, Monika,Wu, Huabin,Blosser, Sarah L.,Vittoria, Marc A.,Arora, Paramjit S.
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supporting information
p. 6932 - 6940
(2015/06/16)
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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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- 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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- Reductive coupling of disulfides and diselenides with alkyl halides catalysed by a silica-supported phosphine rhodium complex using hydrogen as a reducing agent
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The reductive coupling of disulfides and diselenides with alkyl halides was achieved in THF at 65 °C in the presence of 3 mol% of a silica-supported phosphine rhodium complex and triethylamine using hydrogen as a reducing agent, affording a variety of unsymmetrical sulfides and selenides in high yields. The heterogeneous rhodium catalyst can be recovered by a simple filtration and reused several times without significant loss of activity. Reaction with an acyl halide was also observed.
- Zhang, Hean,Hu, Mangen,Cai, Mingzhong
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p. 645 - 647
(2013/11/06)
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- Mechanistic investigation of the oxidation of hydrazides: Implications for the activation of the TB drug isoniazid
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Aryl hydrazides are oxidised to acyl radicals through a mechanism involving diimide intermediates that are prone to nucleophilic acyl substitution. This oxidation occurs regardless of the oxidant involved, however there is no evidence that the acyl radical formed undergoes further oxidation to the corresponding acylium ion, even in the presence of strong oxidants. This study may provide insight into the mechanism of isoniazid resistance in Mycobacterium tuberculosis. The Royal Society of Chemistry.
- Amos, Ruth I. J.,Gourlay, Brendon S.,Yates, Brian F.,Schiesser, Carl H.,Lewis, Trevor W.,Smith, Jason A.
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p. 170 - 176
(2013/02/23)
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- On water preparation of phenylselenoesters
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PhSeZn-halides react under "on water" mild conditions with acid chlorides to provide a high yield route to a variety of aromatic and aliphatic phenylselenoesters.
- Santi, Claudio,Battistelli, Benedetta,Testaferri, Lorenzo,Tiecco, Marcello
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supporting information; experimental part
p. 1277 - 1280
(2012/06/04)
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- Synthesis of selenol esters from diorganyl diselenides and acyl chlorides under solvent-free conditions and microwave irradiation
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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
- Godoi, Marcelo,Ricardo, Eduardo W.,Botteselle, Giancarlo V.,Galetto, Fabio Z.,Azeredo, Juliano B.,Braga, Antonio L.
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supporting information; experimental part
p. 456 - 460
(2012/03/26)
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- Ionic liquid/PPh3 promoted cleavage of diphenyl disulfide and diselenide: A straight-forward metal-free one-pot route to the synthesis of unsymmetrical sulfides and selenides
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A metal-free cleavage of diphenyl disulfide and diphenyl diselenide has been achieved using ionic liquid/triphenyl phosphine (PPh3) and a convenient protocol for the one-pot synthesis of unsymmetrical sulfides and selenides by condensing 'in situ' generated thiolate or selenate anion with alkyl halides has been developed. In addition, 1,4-conjugate addition of the generated thiolate anions to activated alkenes has also been demonstrated. The ionic liquid, 1-methyl-3-pentyl imidazolium bromide, [pmIm]Br plays a crucial role in promoting the course of the reactions and shows superior activity and selectivity compared to other solvents. The [pmIm]Br has been reused for at least five times without appreciable loss of activity.
- Banerjee, Subhash,Adak, Laksmikanta,Ranu, Brindaban C.
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supporting information; experimental part
p. 2149 - 2152
(2012/05/05)
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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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- Zn in ionic liquid: An efficient reaction media for the synthesis of diorganyl chalcogenides and chalcogenoesters
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A straightforward and efficient methodology is described to synthesize structurally diverse diorganyl selenides, sulfides, seleno- and thioesters by using commercially available Zn dust in ionic liquid. Excellent yields were achieved under neutral conditions at room temperature in a short time. The solvent/ionic liquid is reusable and exhibited higher performance as compared with organic solvents.
- Narayanaperumal, Senthil,Alberto, Eduardo E.,Gul, Kashif,Kawasoko, Cristiane Yuriko,Dornelles, Luciano,Rodrigues, Oscar E.D.,Braga, Antonio Luiz
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experimental part
p. 4723 - 4730
(2011/06/27)
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- Bimetallic system for the synthesis of diorganyl selenides and sulfides, chiral β-seleno amines, and seleno- and thioesters
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The bimetallic reagent Sn(II)/Cu(II) in [bmim]BF4 was efficiently used for the cleavage of diaryl diselenides and disulfides and reacts with a variety of organic substrates, such as organic halides, acid chlorides, and β-amino mesylates affording the diorganyl selenides and sulfides within very short reaction times, under mild conditions and with excellent yields, using BMIM-BF4 as a reusable solvent.
- Gul, Kashif,Narayanaperumal, Senthil,Dornelles, Luciano,Rodrigues, Oscar E.D.,Braga, Antonio Luiz
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supporting information; experimental part
p. 3592 - 3596
(2011/07/31)
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- Efficient ring opening of protected and unprotected aziridines promoted by stable zinc selenolate in ionic liquid
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A highly efficient protocol is reported for the synthesis of chiral β-seleno amines via the ring-opening reaction of aziridines. Under neutral conditions, employing a stable phenyl selenolate specie (PhSeZnBr) and (BMIM)BF4 as solvent, β-seleno
- Salman, Syed M.,Schwab, Ricardo S.,Alberto, Eduardo E.,Vargas, Josimar,Dornelles, Luciano,Rodrigues, Oscar E. D.,Braga, Antonio L.
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supporting information; scheme or table
p. 69 - 72
(2011/02/25)
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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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- An approach to the synthesis of thioesters and selenoesters promoted by rongalite?
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Rongalite? promotes cleavage of diaryldisulfides generating the corresponding chalcogenolate anions that then undergo facile reaction with N-acylbenzotriazoles in the presence of K2CO3 to afford thioesters in good to excel
- Lin, Shao-Miao,Zhang, Ji-Lei,Chen, Jiu-Xi,Gao, Wen-Xia,Ding, Jin-Chang,Su, Wei-Ke,Wu, Hua-Yue
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experimental part
p. 1616 - 1620
(2010/11/17)
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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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- 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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- 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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- Efficient synthesis of selenoesters from acyl chlorides mediated by CuO nanopowder in ionic liquid
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Herein, we report an eco-friendly synthesis of selenoesters from acyl chlorides catalyzed by recyclable CuO nanopowder in ionic liquid as a recyclable solvent in good to excellent yields. This protocol shows high efficiency in catalyzing this transformati
- Singh, Devender,Narayanaperumal, Senthil,Gul, Kashif,Godoi, Marcelo,Rodrigues, Oscar Endrigo Dorneles,Braga, Antonio Luiz
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scheme or table
p. 957 - 960
(2010/07/14)
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- Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide: efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters
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A convenient and efficient method was developed for the synthesis of alkyl phenyl selenides, sulfides, and selenoesters in one-pot reaction by using indium metal. The reaction showed the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides. For the reaction of primary and secondary alkyl iodides and bromides, the yields of selenides were improved by the addition of a catalytic amount of iodine.
- Munbunjong, Wanida,Lee, Eun Hwa,Ngernmaneerat, Poonlarp,Kim, Sung Jun,Singh, Gurpinder,Chavasiri, Warinthorn,Jang, Doo Ok
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experimental part
p. 2467 - 2471
(2009/08/15)
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- On the reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur and selenium) towards organyl halides for the synthesis of organyl phenyl chalcogenides
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The reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur, selenium) towards organyl halides (organyl = alkyl, allyl, benzyl, acyl) was examined. A practical one-pot method to prepare organyl phenyl chalcogenides indium metal and diphenyl dichalcogenide was found. The coupling is fairly broad in scope and generally works better organyl halides capable to produce stable carbocations.
- Peppe, Clovis,Borges De Castro, Lierson
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experimental part
p. 678 - 683
(2009/10/30)
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- Efficient synthesis of selenol esters from acid chlorides mediated by indium metal
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This article describes an efficient and easy one-pot route for the synthesis of a wide range of selenol esters from acyl chloride with diselenides in the presence of indium metal. A variety of functional groups can be tolerated within the diorgano diselenide and the acyl chloride coupling partner.
- Marin, Graciane,Braga, Antonio L.,Rosa, Anderson S.,Galetto, Fábio Z.,Burrow, Robert A.,Gallardo, Hugo,Paix?o, Marcio W.
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supporting information; experimental part
p. 4614 - 4618
(2009/10/02)
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- Transition-metal-catalyzed regioselective aroyl- and trifluoro- acetylthiolation of alkynes using thioesters
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Intermolecular CO-retained carbothiolation of alkynes using thioesters took place to afford β-SR substituted enone derivatives; the choice of catalyst (Pd(dba)2-dppe) and the introduction of a CF3 group into the thioesters are the key to achieving the transformation. The Royal Society of Chemistry 2009.
- Minami, Yasunori,Kuniyasu, Hitoshi,Miyafuji, Kiyoshi,Kambe, Nobuaki
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experimental part
p. 3080 - 3082
(2009/12/01)
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- 1-(organoselanyl)perfluoroalkanols: A stable and efficient precursor for organoselenols
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The 1-(organoselanyl)perfluoroalkanols 1, 3, 4, and 10 were successfully prepared and reactions with hexanoyl chlorides to produce the corresponding esters 5, 7, and 8, accompanied by the selenoesters 6 were conducted. The DBU-mediated alkylations of the heptafluorobutanols 4, 10, and the α-p-nitro-benzoate 2 with alkyl halides easily provided alkyl phenyl selenides 9a-9i and 11a-11c in good to high yields. Copyright
- Yamamoto, Terahisa,Moriura, Eri,Sawa, Arisa,Yoshimatsu, Mitsuhiro
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experimental part
p. 1046 - 1047
(2009/12/03)
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- Rhodium-catalyzed reductive coupling of disulfides and diselenides with alkyl halides, using hydrogen as a reducing agent
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(Chemical Equation Presented) We have established that RhCl(PPh 3)3 catalyzes a reductive coupling of disulfides and diselenides with alkyl halides in the presence of triethylamine using hydrogen as a reducing agent. This reaction serves as a convenient new method to produce unsymmetrical sulfides and selenides from disulfides and diselenides instead of unstable and odoriferous thiols and selenols.
- Ajiki, Kaori,Hirano, Masao,Tanaka, Ken
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p. 4193 - 4195
(2007/10/03)
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- Employment of palladium pincer-complexes in phenylselenylation of organohalides
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Palladium pincer-complex-catalyzed selenylation of propargyl-, allyl-, benzyl-, and benzoyl halides could be achieved under mild reaction conditions employing trimethylstannylphenylselenide as selenylating agent. This reaction has a high functional group
- Wallner, Olov A.,Szabo, Kalman J.
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p. 9215 - 9221
(2007/10/03)
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- Reductive cleavage of the Se-Se bond in the presence of a Zn/AlCl 3 system: Synthesis of selenol esters
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Selenol esters were prepared in good yields by reacting diselenides with carboxylic acid anhydrides in dry acetonitrile in the presence of a Zn/AlCl 3 system.
- Movassagh, Barahman,Shamsipoor, Mojgan,Joshaghani, Mohammad
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p. 148 - 149
(2007/10/03)
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- Cleavage of Se-Se bond by Sm/cat.CoCl2 system: A facile and novel method for the preparation of selenoesters
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The Sm/cat.CoCl2 system promoted diselenides to react with anhydrides or acyl chlorides to afford selenoesters in good yields under mild and neutral conditions.
- Chen,Su
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p. 492 - 494
(2007/10/03)
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- Indium(I) iodide-promoted cleavage of diaryl diselenides and disulfides and subsequent condensation with alkyl or acyl halides. One-pot efficient synthesis of diorganyl selenides, sulfides, selenoesters, and thioesters
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Diphenyl diselenides and disulfides undergo facile cleavages by indium(I) iodide and the corresponding generated selenate and thiolate anions condense in situ with alkyl or acyl halides present in the reaction mixture. Thus, a simple, efficient, and general procedure has been developed for the synthesis of unsymmetrical diorganyl selenides, sulfides (thioethers), selenoesters, and thioesters by this one-pot reaction at room temperature.
- Ranu, Brindaban C.,Mandal, Tanmay
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p. 5793 - 5795
(2007/10/03)
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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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- Indium(I) iodide-mediated cleavage of diphenyl diselenide. An efficient one-pot procedure for the synthesis of unsymmetrical diorganyl selenides
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(Matrix presented) A simple and efficient procedure has been developed for the synthesis of unsymmetrical diorganyl selenides through a one-pot indium(I) iodide-mediated reaction of alkyl halide and diphenyl diselenide in methylene chloride at room temperature.
- Ranu, Brindaban C.,Mandal, Tanmay,Samanta, Sampak
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p. 1439 - 1441
(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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- One-pot synthetic method of unsymmetrical diorganyl selenides: Reaction of diphenyl diselenide with alkyl halides in the presence of lanthanum metal
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A convenient synthetic method of unsymmetrical selenides has been developed. When diphenyl diselenide was allowed to react with two equimolar amounts of primary alkyl iodides and bromides in the presence of an equimolar amount of lanthanum metal, alkyl ph
- Nishino, Toshiki,Okada, Mitsuo,Kuroki, Takamasa,Watanabe, Toshihisa,Nishiyama, Yutaka,Sonoda, Noboru
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p. 8696 - 8698
(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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- Cleavage of Se-Se bond by Sm/cat. Cocl2 system: A novel method for the synthesis of selenoesters
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The Sm/cat. COCl2 system promoted desalinates to react with anhydrides or acyl chlorides to afford selenoesters in good yield under mild and neutral conditions.
- Chen, Rener,Zhang, Yongmin
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p. 1331 - 1336
(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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- Reductive cleavage of the Se-Se bond by the Sm/CrCl3 system: A novel one-pot method for the synthesis of selenoesters
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Diaryl diselenides can react with acid chlorides or acid anhydrides in one-pot by the Sm/CrCl3 system to give selenoesters in moderate to good yields under mild and neutral conditions.
- Liu, Yunkui,Zhang, Yongmin
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p. 4043 - 4049
(2007/10/03)
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- Low-valent titanium induced reductive coupling of diaryl diselenides with acid chlorides or acid anhydrides: facile synthesis of selenoestersf
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Selenoesters have been prepared in good yieFd b'yreaction of diaryl diselenides with acid chlorides or acid anhydrides induced by the TiCI4-Sm-THF system under mild reaction conditions.
- Zhouf, Long-Hu,Zhang, Yong-Min
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