Advances in organic tellurium chemistry

Petragnani, Nicola; Stefani, Hélio A.

doi:10.1016/j.tet.2004.11.076

Cited by 153 publications

(46 citation statements)

References 259 publications

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“…Heteroaryl tellurides are usually prepared from the corresponding heteroaryllithium reagents after reaction with elemental tellurium an subsequent reaction with an alkyl halide, 431 although a method consisting of microwave-assisted copper-catalyzed coupling of diaryl dichalcogenides and aryl halides has been recently developed. 432 These tellurides have been found as suitable counterparts for some palladium-catalyzed cross-coupling reactions.…”

Section: Tellurium Heterocyclesmentioning

confidence: 99%

Metalated Heterocycles in Organic Synthesis: Recent Applications

2007

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Section: Tellurium Heterocyclesmentioning

confidence: 99%

Metalated Heterocycles in Organic Synthesis: Recent Applications

2007

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“…Tellurium is a chemical element showing this kind of soft interactions, also known as secondary bonding (Alcock, 1972). Organotellurium compounds have been investigated mainly in organic synthesis (Singh & Sharma, 2000;Petragnani & Stefani, 2005), but also in medicine (Ba et al, 2010), in materials science (Steigerwald & Sprinkle, 1987;Hails et al, 2001) and recently in polymerization processes (organotellurium-mediated living radical polymerization (TERP)) (Kitayama et al, 2010) and to protect materials (lubricants, polymers) from oxidation (Shanks et al, 2006). The type of the Te···X interaction (and the secondary bonding interaction) and its relevance in the tellurium coordination polyhedra have been discussed (Alcock, 1972;ZukermanSchpector & Haiduc, 2001).…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Arrangements in Organotellurium Compounds via Te···Halogen Contacts

Álvarez‐Larena¹,

Farran²,

Piniella³

2011

Current Trends in X-Ray Crystallography

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“…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.

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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...

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Advances in organic tellurium chemistry

Cited by 153 publications

References 259 publications

Metalated Heterocycles in Organic Synthesis: Recent Applications

Metalated Heterocycles in Organic Synthesis: Recent Applications

Supramolecular Arrangements in Organotellurium Compounds via Te···Halogen Contacts

Iron-catalyzed coupling reactions of vinylic chalcogenides with Grignard reagents

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