Short and efficient preparation of alkynyl selenides, sulfides and tellurides from terminal alkynes

Bieber, Lothar W.; Silva, Margarete F. da; Menezes, Paulo H.

doi:10.1016/j.tetlet.2004.02.042

Cited by 97 publications

(31 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Commercial metal carbonyls Cr(CO) 6 , Mo(CO) 6 and W(CO) 6 were used without additional purification. PhC 2 TeFc was prepared following the reported procedure [10]. Diferrocenylditelluride (Fc 2 Te 2 ) was prepared by a slightly modified procedure [11].…”

Section: General Proceduresmentioning

confidence: 99%

Step-by-step transformations of ferrocenyltellurium complexes of Group VIB metal carbonyls

Mathur

Tauqeer

Torubaev

et al. 2014

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

Section: General Proceduresmentioning

confidence: 99%

Step-by-step transformations of ferrocenyltellurium complexes of Group VIB metal carbonyls

Mathur

Tauqeer

Torubaev

et al. 2014

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

“…[21] Lothar et al have also reported that in the presence of K 2 CO 3 and a catalytic amount of copper(I), diphenyl disulfide and ditelluride reacted with terminal alkynes to give alkynyl sulfides and tellurides. [22] These results prompted us to investigate the reaction of diaryl disulfides with terminal alkynes in the presence of a catalytic amount of cesium hydroxide.…”

Section: Stereoselective Synthesis Of (Z)-12-diarylthio-1-alkene Viamentioning

confidence: 99%

Stereoselective Synthesis of (Z)-1,2-Diarylthio-1-alkene via the Reaction of Diaryl Disulfides with Terminal Alkynes Catalyzed by Cesium Hydroxide

Zhang

Yin

Liu

et al. 2009

Synthetic Communications

View full text Add to dashboard Cite

“…The multiple applications of organochalcogenium chemistry have been well described in a number of review articles [1][2][3][4][5][6] and books. [7][8][9][10][11] Functionalized alkynyl [12][13][14][15][16][17][18] and alkenyl [19][20][21][22][23] chalcogenides have a great potential in organic synthesis, since they are valuable intermediates for the selective preparation of several organic compounds.…”

Section: Introductionmentioning

confidence: 99%

Iron-catalyzed coupling reactions of vinylic chalcogenides with Grignard reagents

Silveira¹,

Mendes²,

Wolf³

2010

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Este trabalho descreve um novo método para a reação de acoplamento entre selenetos e teluretos vinílicos e reagentes de Grignard, catalisada por Fe(acac) 3 e à temperatura ambiente. A reação ocorre com retenção da configuração, fornecendo os respectivos alquenos em bons a excelentes rendimentos. Este método também é eficiente para a reação de acoplamento de calcogenetos bisvinílicos com reagentes de Grignard.A general new method for the cross-coupling reaction between vinylic selenides and tellurides and Grignard reagents catalyzed by Fe(acac) 3 at room temperature is described. This reaction proceeded with retention of configuration, providing the respective alkenes in good to excellent yields. This method is also efficient for the coupling reaction of divinyl chalcogenides with Grignard reagents. Keywords: iron-catalyzed, vinylic chalcogenides, cross-coupling, Grignard reagents IntroductionOrganochalcogenium compounds became the key component of a variety of versatile and useful reagents for organic synthesis. The multiple applications of organochalcogenium chemistry have been well described in a number of review articles 1-6 and books. 7-11 Functionalized alkynyl 12-18 and alkenyl [19][20][21][22][23] chalcogenides have a great potential in organic synthesis, since they are valuable intermediates for the selective preparation of several organic compounds.Among the many applications of vinylic selenides, divinylic selenides and vinylic sulfides, the cross-coupling reaction with Grignard reagents catalyzed by Ni 18,24-27 and Pd 28,29 to give the corresponding cross-coupled products, has been described. On the other hand, Pd 19,30 and Ni 24,[31][32][33] catalyzed cross coupling reactions and tellurium/metal exchange reactions [34][35][36][37][38][39][40][41][42] are demonstrative of the usefulness of vinylic tellurides.Transition-metal-catalyzed C-C bond coupling reactions are very important in many areas of science. 43,44 Most current methods require expensive transitionmetal catalysts and ligands. However, in the last years Fe-catalyzed C-C bond cross coupling reactions of vinylic substrates and Grignard reagents became a subject of intense interest. [45][46][47][48][49][50][51] The vinylic counterpart is quite broad in scope, since vinylic halides, triflates, sulfonates, tosylates and enol phosphates can be used. [45][46][47][48][49][50][51] In continuation to our interest on the synthesis and synthetic applications of vinylic chalcogenides 52-58 we decided to study the feasibility of their use in cross coupling reaction with Grignard species catalyzed by iron. To the best of our knowledge, iron catalysts have never been used for the coupling of vinylic selenides and tellurides as electrophiles. The possible use of iron catalysts would represent a great improvement over the high cost of palladium precursors and from the concerns about the toxicity of nickel salts. In light of the above comments it is of interest to design a simple, efficient, and versatile method for the stereoselective coupling of vinylic se...

show abstract

Short and efficient preparation of alkynyl selenides, sulfides and tellurides from terminal alkynes

Cited by 97 publications

References 21 publications

Step-by-step transformations of ferrocenyltellurium complexes of Group VIB metal carbonyls

Step-by-step transformations of ferrocenyltellurium complexes of Group VIB metal carbonyls

Stereoselective Synthesis of (Z)-1,2-Diarylthio-1-alkene via the Reaction of Diaryl Disulfides with Terminal Alkynes Catalyzed by Cesium Hydroxide

Iron-catalyzed coupling reactions of vinylic chalcogenides with Grignard reagents

Contact Info

Product

Resources

About