Vinyllithiums from butyl-vinyl tellurides and bis-vinyl tellurides

Barros, S. M.; Comasseto, J. V.; Berriel, J.

doi:10.1016/s0040-4039(00)70695-2

Cited by 99 publications

(21 citation statements)

References 8 publications

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“…The tellurium precursors of the Z-vinyllithiums are the vinylbutyltellurides, introduced by us as source of Z-vinyllithiums in 1989, since the initially used Z-vinylaryltellurides 43 give mixtures of vinyl and aryllithiums as demonstrated by us in our original report 44 (Scheme 14).…”

Section: Intramolecular Hydrotellurationmentioning

confidence: 99%

Hydrotelluration of alkynes: a unique route to Z-vinyl organometallics

Vieira¹,

Zinn²,

Comasseto³

2001

J. Braz. Chem. Soc.

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A reação de hidroteluração de alquinos é revisada. A transformação de teluretos vinílicos em organometálicos vinílicos reativos e as reações de acoplamento de teluretos vinílicos com alquinos e organometálicos são apresentadas.The hydrotelluration reaction of alkynes is reviewed. The transformation of vinylic tellurides into reactive vinyl organometallics and the coupling reactions of vinylic tellurides with alkynes and organometallics are presented.

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Section: Intramolecular Hydrotellurationmentioning

confidence: 99%

Hydrotelluration of alkynes: a unique route to Z-vinyl organometallics

Vieira¹,

Zinn²,

Comasseto³

2001

J. Braz. Chem. Soc.

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“…Vinylic tellurides are intermediates in the synthesis of vinyllithium compounds (Barros, Comasseto & Berriel, 1989), which are, in turn, important intermediates in organic synthesis, either as precursors of the widely used vinylcuprate compounds or as nucleophiles leading to chain elongation products by reaction with many electrophiles (Comasseto & Berriel, 1990;Lipshutz, 1989). The crystal structure determination of compound (1) was…”

Section: Commentmentioning

confidence: 99%

Dichloro[(Z)-2-chloro-2-phenylvinyl](4-methoxyphenyl)tellurium(IV)

Zukerman-Schpector¹,

Comasseto²,

Stefani³

1995

Acta Crystallogr C

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“…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.…”

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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Vinyllithiums from butyl-vinyl tellurides and bis-vinyl tellurides

Cited by 99 publications

References 8 publications

Hydrotelluration of alkynes: a unique route to Z-vinyl organometallics

Hydrotelluration of alkynes: a unique route to Z-vinyl organometallics

Dichloro[(Z)-2-chloro-2-phenylvinyl](4-methoxyphenyl)tellurium(IV)

Iron-catalyzed coupling reactions of vinylic chalcogenides with Grignard reagents

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