63707-10-8Relevant academic research and scientific papers
New arylselanylpyrazole-copper catalysts: Highly efficient catalytic system for C–Se and C–S coupling reactions
Coelho, Felipe Lange,Dresch, Lucielle Codeim,Stieler, Rafael,Campo, Leandra Franciscato,Schneider, Paulo Henrique
, p. 19 - 26 (2019/01/04)
We describe herein the use of arylselanylpyrazole–copper complexes as versatile catalysts for C–Se and C–S coupling reactions. The performance of these complexes for C–Se reactions was investigated in chalcogenoacetylene synthesis. The reactions were carried out under mild and aerobic conditions and afforded selanylalkynes bearing a variety of electron-withdrawing and electron-donating groups. The performance of these catalysts for C–S coupling was investigated through the reaction of aryl halides with thiols and products were obtained in moderate to excellent yields. A plausible mechanism for selenoacetylene synthesis is also suggested, and the 77Se NMR results show that these arylselanylpyrazole ligands act as hemilabile ligands. High-resolution mass spectrometry was used to investigate the intermediates and also to corroborate the proposed catalytic cycle.
Alkynylthioimidazolium Salts: Efficient Reagents for the Synthesis of Alkynyl Sulfides by Electrophilic Thioalkynylation
Pe?a, Javier,Talavera, Garazi,Waldecker, Bernd,Alcarazo, Manuel
, p. 75 - 78 (2017/01/09)
The efficient synthesis of a series of alkynylthioimidazolium salts through reaction of organozinc compounds with dibromo(imidazolium)sulfuranes is reported. Addition of Grignard reagents to these new species provided a highly modular, clean, and scalable access to a broad variety of alkynyl sulfides in good-to-excellent yields. The utility of this protocol was showcased by the preparation of alkynyl sulfides, which are particularly difficult to obtain or simply unavailable through the existing methodologies. In addition, the synthetic method was extended to the preparation of alkynyl selenides.
A General and highly efficient protocol for the synthesis of chalcogenoacetylenes by copper(I)-terpyridine catalyst
Movassagh, Barahman,Yousefi, Ali,Momeni, Badri Zaman,Heydari, Sepideh
, p. 1385 - 1390 (2014/06/23)
A highly efficient copper-catalyzed Csp-X (X = S, Se, Te) bond-forming reaction of terminal alkynes and diorganyl dichalcogenides has been developed. This transformation was realized through the use of copper(I) iodide as a catalyst, 4′-(4-meth
Cryptand-22 as an efficient ligand for the copper-catalyzed cross-coupling reaction of diorgano dichalcogenides with terminal alkynes leading to the synthesis of alkynyl chalcogenides
Mohammadi, Elmira,Movassagh, Barahman
, p. 1613 - 1615 (2014/03/21)
A general and efficient method for the cross-coupling reaction of diorgano dichalcogenides with terminal alkynes using copper iodide/cryptand-22 (CuI/C22) has been developed. This protocol gave alkynyl chalcogenides in moderate to excellent yields in the
Magnetite (Fe3O4) nanoparticles: An efficient and recoverable catalyst for the synthesis of alkynyl chalcogenides (selenides and tellurides) from terminal acetylenes and diorganyl dichalcogenides
Godoi, Marcelo,Liz, Daiane G.,Ricardo, Eduardo W.,Rocha, Manuela S.T.,Azeredo, Juliano B.,Braga, Antonio L.
, p. 3349 - 3354 (2014/05/06)
We present herein a new and efficient methodology for the synthesis of alkynyl chalcogenides from terminal acetylenes and diorganyl dichalcogenides, catalyzed by Fe3O4 nanoparticles. This new approach provided the desired products in good to excellent yields. Moreover, the catalyst was easily recoverable using an external magnet and reused for further experiments without loss of catalytic activity.
A general and green procedure for the synthesis of organochalcogenides by CuFe2O4 nanoparticle catalysed coupling of organoboronic acids and dichalcogenides in PEG-400
Kundu, Debasish,Mukherjee, Nirmalya,Ranu, Brindaban C.
, p. 117 - 125 (2013/04/10)
A general and efficient procedure has been developed for the synthesis of organochalcogenides (selenides and tellurides) by a simple reaction of organoboronic acids and dichalcogenides catalysed by CuFe2O 4 nanoparticles in PEG-400 without any ligand. This protocol offers the scope for access to a wide spectrum of chalcogenides including diaryl, aryl-heteroaryl, aryl-styrenyl, aryl-alkenyl, aryl-allyl, aryl-alkyl and aryl-alkynyl versions. The catalyst is magnetically separable and recyclable eight times without any loss of appreciable catalytic activity. The products are obtained in high purities after evaporation of solvent followed by filtration column chromatography. The Royal Society of Chemistry.
An efficient synthesis of alkynyl selenides and tellurides from terminal acetylenes and diorganyl diselenides or ditellurides catalyzed by recyclable copper oxide nanopowder
Godoi, Marcelo,Ricardo, Eduardo W.,Frizon, Tiago E.,Rocha, Manuela S. T.,Braga, Antonio Luiz,Singh, Devender,Paixao, Marcio W.
, p. 10426 - 10430,5 (2012/12/12)
Herein, we report an efficient method for the synthesis of alkynyl selenides and tellurides from terminal alkynes and diorganyl diselenides or ditellurides using CuO nanopowder as a recyclable catalyst. This new methodology furnished the desired products in good to excellent yields. Furthermore, the catalyst was easily recovered and reused for further catalytic reactions without loss of activity.
An efficient and general procedure for the synthesis of alkynyl chalcogenides (selenides and tellurides) by alumina-supported Cu(II)-catalyzed reaction of alkynyl bromides and diphenyl dichalcogenides
Ahammed, Sabir,Bhadra, Sukalyan,Kundu, Debasish,Ranu, Brindaban C.,Sreedhar, Bojja
, p. 10542 - 10549,8 (2012/12/12)
Alumina (Al2O3) supported Cu(II) efficiently catalyzes the reaction of alkynyl bromides and diphenyl diselenides and ditellurides in presence of Zn dust or indium(I) bromide to provide the corresponding alkynyl selenides and tellurides. The reactions of a wide variety of substituted alkynyl bromides have been addressed. The zinc dust or InBr is required for the cleavage of diphenyl selenides/tellurides. The mechanism of the reaction is established. The yields of products are high and the catalyst is recycled.
An efficient and general procedure for the synthesis of alkynyl chalcogenides (selenides and tellurides) by alumina-supported Cu(II)-catalyzed reaction of alkynyl bromides and diphenyl dichalcogenides
Ahammed, Sabir,Bhadra, Sukalyan,Kundu, Debasish,Sreedhar, Bojja,Ranu, Brindaban C.
, p. 10542 - 10549 (2013/01/15)
Alumina (Al2O3) supported Cu(II) efficiently catalyzes the reaction of alkynyl bromides and diphenyl diselenides and ditellurides in presence of Zn dust or indium(I) bromide to provide the corresponding alkynyl selenides and tellurides. The reactions of a wide variety of substituted alkynyl bromides have been addressed. The zinc dust or InBr is required for the cleavage of diphenyl selenides/tellurides. The mechanism of the reaction is established. The yields of products are high and the catalyst is recycled.
Chalcogenoacetylenes obtained by indium(III) catalysis: Dual catalytic activation of diorgano dichalcogenides and Csp-H bonds
Rampon, Daniel S.,Giovenardi, Rodrigo,Silva, Tiago L.,Rambo, Raoni S.,Merlo, Aloir A.,Schneider, Paulo H.
experimental part, p. 7066 - 7070 (2012/01/04)
A new approach for the one-pot synthesis of alkynyl chalcogenides, exemplified mainly by selenides, was developed in which dual activation of diorgano dichalcogenides and terminal acetylenes is achieved by using an indium(III) catalyst. The method has adv
