Methodologies Limiting or Avoiding Contamination by Organotin Residues in Organic Synthesis

Grognec, Erwan Le; Chrétien, Jacques R.; Zammattio, Françoise; Quintard, Jean‐Paul

doi:10.1021/acs.chemrev.5b00196

Cited by 84 publications

(53 citation statements)

References 418 publications

(609 reference statements)

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“…However, organotin chemistry presents some disadvantages, such as the contamination of the obtained conjugated materials by tin salts and the difficulties of separation. Efforts have been made to overcome these problems, leading, for example, to the development of synthetic methods using organotin reagents supported on polymers or ionic liquids . Additionally, it has been shown that Stille cross‐coupling reactions with organotin reagents supported on an ionic liquid could be performed without solvent or additive by using commercially available catalysts , .…”

Section: Resultsmentioning

confidence: 99%

Toward Sustainable Organic Semiconductors from a Broad Palette of Green Reactions

et al. 2017

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New conjugated materials, based on the triphenylamine‐thiophene moiety and integrating azomethine bonds with a dibenzofuran unit or a cyanovinyl bond with a phenylthiophene or bithiophene unit, have been synthesized by using a wide range of green reactions such as direct heteroarylation coupling reactions, Knoevenagel and Schiff‐base condensations and Stille cross‐coupling reactions using ionic‐liquid‐supported thiophenylstannane. The electronic properties of the new molecules were analyzed by UV/Vis spectroscopy and cyclic voltammetry. The potential use of the molecules as donor materials for photovoltaic conversion were evaluated in simple bilayer solar cells using C60 as the acceptor material.

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Section: Resultsmentioning

confidence: 99%

Toward Sustainable Organic Semiconductors from a Broad Palette of Green Reactions

et al. 2017

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“…Our initial interest was in performing radical ring‐closing reactions in a catalytic manner from trichloroacetamides by using a supported tin hydride reagent, generated in situ by a reducing agent (e.g., NaBH 4 ). The few examples of reductive radical cyclization using grafted polymers with organotin reagents feature bromides as proradical carbon‐center species . In order to apply this chemistry to the radical cyclization of trichloroacetamides, we decided to use a stannylated polynorbornene, which was reported and recently employed by Albéniz for radical reductive bromoaryl reduction processes using polymethylhydrosiloxane (PMHS) as a reductor …”

Section: Resultsmentioning

confidence: 99%

Synthesis of α‐Chlorolactams by Cyanoborohydride‐Mediated Radical Cyclization of Trichloroacetamides

Coussanes

Jakobi

Lindell

et al. 2018

Chemistry A European J

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A cyanoborohydride-promoted radical cyclization methodology has been developed to access α-chlorolactams in a simple and efficient way using NaBH CN and trichloroacetamides easily available from allylic and homoallylic secondary amines. This methodology allowed the synthesis of a library of α-chlorolactams (mono- and bicyclic), which were tested for herbicidal activity, trans-3-chloro-4-methyl-1-(3-trifluoromethyl)phenyl-2-pyrrolidinone being the most active.

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“…This strategy constitutes a promising approach to iminosugar C‐glycosides, as exemplified in a preliminary report. [3d] It is noteworthy that the use of organotin reagents does not cause additional problems in terms of purification due to the polarity of iminosugar C‐glycosides, which allows a facile separation from the apolar tetrabutyltin species …”

Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of Stannylated Dehydropiperidines and Dehydroazepanes

et al. 2016

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An efficient allylation and butenylation of N‐alkoxycarbonyl‐2‐tributylstannyl‐1,3‐oxazolidines derived from (S)‐vinylglycinol or (S)‐styrylglycinol is described. After conversion of the stannylated azadienes into stannylated dienyl oxazolidinones, a ring‐closing metathesis generates dehydropiperidine or dehydroazepane; both are interesting scaffolds for the synthesis of polyfunctionnalized piperidines or azepanes. Whereas the dehydropiperidine synthesis was found to be selective regardless of the Grubbs catalyst used, we found that Grubbs II catalyst induced partial double bond isomerization in the dehydroazepane series. In addition, when allyltrimethylsilane was used in the ring‐opening reactions of N‐alkoxycarbonyl‐2‐tributylstannyl‐1,3‐oxazolidines, cyclopropyl derivatives were selectively obtained.

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Methodologies Limiting or Avoiding Contamination by Organotin Residues in Organic Synthesis

Cited by 84 publications

References 418 publications

Toward Sustainable Organic Semiconductors from a Broad Palette of Green Reactions

Toward Sustainable Organic Semiconductors from a Broad Palette of Green Reactions

Synthesis of α‐Chlorolactams by Cyanoborohydride‐Mediated Radical Cyclization of Trichloroacetamides

Stereoselective Synthesis of Stannylated Dehydropiperidines and Dehydroazepanes

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