Cerium(III)-Mediated Efficient and Stereoselective Hydrochalcogenation of Terminal Alkynes

Silveira, Cláudio C.; Mendes, Samuel R.; Rosa, Daniel De; Zeni, Gilson

doi:10.1055/s-0029-1217029

Cited by 18 publications

(6 citation statements)

References 17 publications

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“…Some other recent protocols of interest, because they are related to the theme of this review, include the CeCl 3 -catalyzed hydrochalcogenation of propargylic alcohols and amines, the Cs-catalyzed addition of dichalcogenides to alkynes, and GaCl 3 -mediated disulfidation …”

Section: Catalytic Addition Of Rz−h Derivatives To Alkynes and Allene...mentioning

confidence: 99%

Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

2011

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Section: Catalytic Addition Of Rz−h Derivatives To Alkynes and Allene...mentioning

confidence: 99%

Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

2011

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“…26 Recently, Silveira and coworkers have reported the first methodology of hydrochalcogenation of terminal alkynes promoted by CeCl 3 . 27 In the light of this background that we have studied a convenient procedure for transforming alkynes 9 into the corresponding alkenyl iodides10 using the CeCl 3 •7H 2 O-NaI system.…”

Section: Resultsmentioning

confidence: 99%

A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes

et al. 2010

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The occurrence of unsaturated systems in natural products combined with the mildness and the wide range of applicability of CeCl(3) promoted methodologies suggest several potential future synthetic applications within the field of total synthesis of biologically active molecules. On this concept, the use of CeCl(3).7H(2)O-NaI system as an efficient heterogeneous promoter has been highlighted in the iodofunctionalization of carbon-carbon triple bonds. The study has shown that this method would be particularly interesting for the stereoselective formation of trisubstituted (Z)- or (E)-iodoalkenes by simply changing the nature of the solvent. The methodology has been successfully applied to the synthesis of (R)-1-[4,4-bis-(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid , named (R)-Tiagabine, which is a potent and selective gamma-aminobutyric acid (GABA) uptake inhibitor with proven anticonvulsant efficacy in humans.

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“…Thus, to date, there are several efficient homogeneous and heterogeneous catalytic systems developed based on Pd, Ni, Rh, Au, Zr, Cu, and Cs to obtain various types of vinyl chalcogenides (branched and linear E or Z ) with excellent regio‐ and stereoselectivity starting from various terminal alkynes and thiols (both aromatic and aliphatic) . Large substrate scope and functional group tolerance, as well as the possibility to scale up the reactions and recycle the catalyst, make them highly useful and efficient tools for synthetic applications.…”

Section: Formation Of Monofunctionalized Akenes (Vinyl Chalcogenides)mentioning

confidence: 99%

“…Later Silveira et al found CeCl 3 to be an efficient catalyst for selectivea ddition of in-situ-formed selenolates and tellurolates to propargylic alcohols and amines resulting in linear products of Z-configuration (Scheme 21). [41] The solventh ad ac rucial effect on regioselectivity of the reaction, with the best results being achieved in iPrOH.T od ate, this is the only example of vinyl telluride formation via addition to the triple bond of alkynes.…”

Section: Catalytic Systems Leading To Anti-markovnikov-type (Linear) mentioning

confidence: 99%

Metal Catalysis in Thiolation and Selenation Reactions of Alkynes Leading to Chalcogen-Substituted Alkenes and Dienes

Orlov

2015

ChemistryOpen

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This review covers recent achievements in metal‐catalyzed Z−H and Z−Z (Z=S, Se) bond addition to the triple bonds of alkynes—a convenient and atom‐efficient way to carbon‐element bond formation. Various catalytic systems (both homogeneous and heterogeneous) developed to date to obtain mono‐ and bis‐chalcogen‐substituted alkenes or dienes, as well as carbonyl compounds or heterocycles, starting from simple and available alkynes and chalcogenols or dichalcogenides are described. The right choice of metal and ligands allows us to perform these transformations with high selectivities under mild reaction conditions, thus tolerating unprotected functional groups in substrates and broadening ways of further modification of the products. The main aim of the review is to show the potential of the catalytic methods developed in synthetic organic chemistry. Thus, emphasis is made on the scope of reactions, types of products that can be selectively formed, convenience, and scalability of the catalytic procedures. A brief mechanistic description is also given to introduce new readers to the topic.

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Cerium(III)-Mediated Efficient and Stereoselective Hydrochalcogenation of Terminal Alkynes

Abstract: C e r i u m (I I I)-M e d i a t e d H y d r o c h a l c o g e n a t i o n o f A l k y n e s

Cited by 18 publications

References 17 publications

Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes

Metal Catalysis in Thiolation and Selenation Reactions of Alkynes Leading to Chalcogen-Substituted Alkenes and Dienes

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