- CuI/glycerol mediated stereoselective synthesis of 1,2-bis-chalcogen alkenes from terminal alkynes: Synthesis of new antioxidants
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(E)-1,2-Bis-chalcogen alkenes were stereoselectively prepared in good yields by the addition of diorganyl dichalcogenides to terminal alkynes using CuI/Zn/glycerol as a recyclable catalytic system. The antioxidant activity in vitro of four (E)-1,2-bis-cha
- Gon?alves, Lóren C.C.,Victória, Francine N.,Lima, David B.,Borba, Pedro M.Y.,Perin, Gelson,Savegnago, Lucielli,Lenard?o, Eder J.
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Read Online
- Simultaneous Construction of C?Se And C?S Bonds via the Visible-Light-Mediated Multicomponent Cascade Reaction of Diselenides, Alkynes, and SO2
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A visible-light mediated multicomponent cascade reaction of diselenides, alkynes, and sulfur dioxide was developed, in which multiple C?Se and C?S bonds were constructed, and unexpected β-sulfonylvinylselane compounds were generated with high selectivity for E configuration. β-Sulfonylvinylselane transformation into 1,4-oxathiine-4,4-dioxide and sulfonylethyne derivates was then investigated. A plausible mechanism involving a selenium radical-initiated cascade reaction and sulfur dioxide insertion was proposed.
- Chen, Hui,Ding, Rui,Tang, Haitao,Pan, Yingming,Xu, Yanli,Chen, Yanyan
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- Synthesis of alkynyltellurides mediated by K3PO4 and DMSO
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In the present work, a simple method for the synthesis of alkynyltellurides is described by the reactions of terminal alkynes with diorganyl ditellurides in the presence of a catalytic amount of K3PO4. In both substrates, it was possible to vary the aryl and alkyl groups, obtaining the products of interest in short reaction times and in yields ranging from 30 to 93%. This methodology, different from those already reported in the literature, has the advantage of using a catalytic amount of a weak base and no use of metallic catalysts.
- Do Sacramento, Manoela,Menezes, Larissa,Goldani, Bruna,Perin, Gelson,Silva, Marcio S.,Barcellos, Thiago,Alves, Diego
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supporting information
p. 11091 - 11098
(2019/07/31)
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- Visible-Light Promoted Stereoselective Arylselanyl Functionalization of Alkynes
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Functionalization of double bonds with arylselenium groups found in the literature, commonly uses high temperatures in the presence of metal catalysts, reducing agents or other additives. In this context, this work presents a series of bis-arylselanyl ole
- Weber, Andressa C. H.,Coelho, Felipe L.,Affeldt, Ricardo F.,Schneider, Paulo H.
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supporting information
p. 6738 - 6742
(2018/11/23)
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- DES as a green solvent to prepare 1,2-bis-organylseleno alkenes. Scope and limitations
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We describe here our results on the use of choline chloride/urea 1:2 as a deep eutectic solvent (DES) in the synthesis of vinyl selenides. A good selectivity for the (E)-1,2-bis-organylseleno alkenes was observed starting from terminal alkynes and diaryl
- Lopes, Eric F.,Gon?alves, Lóren C.,Vinueza, Julio C.G.,Jacob, Raquel G.,Perin, Gelson,Santi, Claudio,Lenard?o, Eder J.
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supporting information
p. 6890 - 6895
(2015/11/27)
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- Bis-vinyl selenides obtained via iron(iii) catalyzed addition of PhSeSePh to alkynes: Synthesis and antinociceptive activity
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In the present study the synthesis and antinociceptive activity of bis-vinyl selenides, prepared via FeCl3 promoted reaction addition of diorganyl dichalcogenides to alkynes, is described. The pharmacological results demonstrated that bis-vinyl selenides 3a, 3d, 3h and 3t elicited antinociceptive effect in the mouse formalin test. The antinociceptive effects of bis-vinyl selenides are not sensitive to electronic effects of the substituents on the aromatic ring directly bonded to the selenium atom. Bis-vinyl selenides 3h and 3t were the most promising molecules for pharmacological purposes since these bis-vinyl selenides were effective in both phases of the formalin test and against edema. A single dose of bis-vinyl selenides 3a, 3d, 3h and 3t did not cause acute toxicity in mice.
- Sartori, Glaubia,Neto, José S.S.,Pesarico, Ana Paula,Back, Davi F.,Nogueira, Cristina W.,Zeni, Gilson
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supporting information
p. 1199 - 1208
(2013/04/10)
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- A simple and stereoselective synthesis of (Z)-1,2-bis-arylselanyl alkenes from alkynes using KF/Al2O3
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The title compounds were synthesized by a one-pot reaction of diaryl diselenides with terminal alkynes avoiding the previous preparation of arylselanyl alkynes. The reactions were performed under mild conditions with a range of terminal alkynes using KF/A
- Lara, Renata G.,Rosa, Paloma C.,Soares, Liane K.,Silva, Marcio S.,Jacob, Raquel G.,Perin, Gelson
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p. 10414 - 10418,5
(2012/12/12)
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- Highly selective perfluoroalkylchalcogenation of alkynes by the combination of iodoperfluoroalkanes and organic dichalcogenides upon photoirradiation
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Vinylic selenides and tellurides are useful synthetic intermediates for preparation of vinylic compounds and carbonyl compounds. Herein we report highly selective perfluoroalkylselenation and -telluration of terminal alkynes by using heteroatom mixed systems, i.e., (PhSe)2/RfI and (PhTe)2/RfI, upon photoirradiation. When the reaction of aromatic alkynes and conjugated enynes with diphenyl diselenide and perfluoroalkyl iodide is conducted in benzotrifluoride (BTF) as solvent upon irradiation with a xenon lamp through Pyrex (hν >300 nm), novel perfluoroalkylselenation of the alkynes takes place regio- and stereoselectively to give 1-(perfluoroalkyl)-2-(phenylseleno)alkenes in good yields. Similar procedure can be applied to photoinduced perfluoroalkyltelluration of aromatic alkynes, and perfluoroalkyl and phenyltelluro groups are introduced to the terminal and internal positions of alkynes regio- and stereoselectively. Since perfluoroalkyl (fluorous) groups make it possible to isolate the products easily by fluorous/organic/aqueous extraction technique, the obtained perfluoroalkylselenation and -telluration products are promising as synthetic intermediates.
- Tamai, Taichi,Nomoto, Akihiro,Tsuchii, Kaname,Minamida, Yoshiaki,Mitamura, Takenori,Sonoda, Motohiro,Ogawa, Akiya
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p. 10516 - 10522,7
(2012/12/12)
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- Cesium Salt-Catalyzed Addition of Diphenyl Dichalcogenides to Alkynes: Selective Synthesis of Bis- and Mono(phenylchalcogeno)alkenes
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A cesium salt has a unique catalytic ability for the reaction of alkynes with diphenyl dichalcogenides. When the diphenyl dichalcogenides, such as the disulfide, diselenide, or ditelluride, were allowed to react with alkynes in the presence of a catalytic
- Nishiyama, Yutaka,Ohnishi, Haruko,Koguma, Yuya
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experimental part
p. 1170 - 1174
(2009/12/25)
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- Hydroselenation of alkynes using NaBH4/BMIMBF4: easy access to vinyl selenides
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A general and easy method for the synthesis of several vinyl selenides using NaBH4 and BMIMBF4 as a recyclable solvent is described. This efficient and improved method furnishes the corresponding vinyl chalcogenides preferentially wi
- Lenard?o, Eder J.,Dutra, Luiz G.,Saraiva, Maiara T.,Jacob, Raquel G.,Perin, Gelson
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p. 8011 - 8013
(2008/03/18)
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- Addition of chalcogenolate anions to terminal alkynes using microwave and solvent-free conditions: Easy access to bis-organochalcogen alkenes
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We present here the reaction of diphenyl dichalcogenides (Se and Te) with propargyl alcohols using alumina supported sodium borohydride under solvent-free conditions. This efficient and improved method is general and furnishes the corresponding vinyl chal
- Perin, Gelson,Jacob, Raquel G.,Dutra, Luiz G.,De Azambuja, Francisco,Dos Santos, Greice F. F.,Lenard?o, Eder J.
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p. 935 - 938
(2007/10/03)
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- Indium(I) bromide-mediated regioselective Markovnikov hydroselenation, diselenation and hydration of terminal alkynes with diphenyldiselenide in aqueous media
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The indium(III) selenolate obtained from indium(I) bromide and diphenyldiselenide promotes, alternatively, the Markovnikov hydroselenation, diselenation or hydration of terminal alkynes, depending on the experimental conditions. Georg Thieme Verlag Stuttgart.
- Peppe, Clovis,Lang, Ernesto Schulz,Ledesma, Gabriela Nanci,De Castro, Liérson Borges,Barros, Olga Soares Do Rego,De Azevedo Mello, Paola
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p. 3091 - 3094
(2007/10/03)
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- Versatile Cyclisation Reactions Using Selenoboranes
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Tris(phenylseleno)borane and tris(methylseleno)borane reacted with terminal acetylenes to afford (Z)-vinyl selenides.This reaction was initiated by oxygen and the intermediates were vinyl radicals.This radical reaction could be applied to the intramolecular free radical cyclisation of enynes and some heterocycles and carbocycles were synthesised.This novel method could be also employed in the synthesis of α-kainoid derivatives.
- Kataoka, Tadashi,Yoshimatsu, Mitsuhiro,Noda, Yoshinori,Sato, Takashi,Shimizu, Hiroshi,Hori, Mikio
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p. 121 - 130
(2007/10/02)
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- A Novel Thermal Addition of Diaryl Diselenides to Acetylenes
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When diphenyl diselenide is heated at 150-180 deg C in the presence of acetylenes, an acetylene insertion reaction into the Se-Se bond of the diselenide takes place to provide vic-bis(phenylseleno)alkenes in moderate to high yields.
- Ogawa, Akiya,Takami, Noriaki,Sekiguchi, Masahito,Yokoyama, Hiroshi,Kuniyasu, Hitoshi,et al.
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p. 2241 - 2242
(2007/10/02)
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- VINYL RADICAL GENERATION WITH SELENOBORANE AND ITS APPLICATION TO CYCLIZATION REACTION OF ENYNES
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Tris(methylseleno)- and tris(phenylseleno)boranes added to acetylenes to afford methylseleno- and phenylseleno-substituted Z-vinylselenides in high yields.The addition reactions proceeded by way of free radicals and were applied to cyclization reactions o
- Kataoka, Tadashi,Yoshimatsu, Mitsuhiro,Shimizu, Hiroshi,Hori, Mikio
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p. 5927 - 5930
(2007/10/02)
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