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• Stille_reaction abstract "The Stille reaction, or the Migita-Kosugi-Stille coupling, is a chemical reaction widely used in organic synthesis which involves the coupling of an organotin compound (also known as organostannanes) with a variety of organic electrophiles via palladium-catalyzed coupling reaction.The R1 group attached to the trialkyltin is normally sp2-hybridized, including alkenes, and aryl groups; however, conditions have been devised to incorporate both sp3-hybridized groups, such as allylic and benzylic substituents, and sp-hybridized alkynes. These organostannanes are also stable to both air and moisture, and many of these reagents are either commercially available or can be synthesized from literature precedent. However, these tin reagents tend to be highly toxic. X is typically a halide, such as Cl, Br, I, yet pseudohalides such as triflates and sulfonates and phosphates can also be used.The groundwork for the Stille reaction was laid by Colin Eaborn, Toshihiko Migita, and Masanori Kosugi in 1976 and 1977, who explored numerous palladium catalyzed couplings involving organotin reagents. John Stille and David Milstein developed a much milder and more broadly applicable procedure in 1978. Stille’s work on this area might have earned him a share of the 2010 Nobel Prize, which was awarded to Richard Heck, Ei-ichi Negishi, and Akira Suzuki for their work on the Heck, Negishi, and Suzuki coupling reactions. However, Stille died in the plane crash of United Airlines Flight 232 in 1989.Several reviews have been published on the Stille reaction.".
• Stille_reaction thumbnail Scheme_for_the_Stille_reaction.png?width=300.
• Stille_reaction wikiPageExternalLink 11_Stille.pdf.
• Stille_reaction wikiPageExternalLink stille-coupling.shtm.
• Stille_reaction wikiPageExternalLink stille-reaction.
• Stille_reaction wikiPageID "1224067".
• Stille_reaction wikiPageLength "48114".
• Stille_reaction wikiPageOutDegree "350".
• Stille_reaction wikiPageRevisionID "704646886".
• Stille_reaction wikiPageWikiLink Acetate.
• Stille_reaction wikiPageWikiLink Acyl_chloride.
• Stille_reaction wikiPageWikiLink Acyl_halide.
• Stille_reaction wikiPageWikiLink Akira_Suzuki_(chemist).
• Stille_reaction wikiPageWikiLink Alcohol.
• Stille_reaction wikiPageWikiLink Alkene.
• Stille_reaction wikiPageWikiLink Alkyl.
• Stille_reaction wikiPageWikiLink Alkyne.
• Stille_reaction wikiPageWikiLink Allyl.
• Stille_reaction wikiPageWikiLink Alpha_and_beta_carbon.
• Stille_reaction wikiPageWikiLink Ammonium_chloride.
• Stille_reaction wikiPageWikiLink Ansamycin.
• Stille_reaction wikiPageWikiLink Antibiotics.
• Stille_reaction wikiPageWikiLink Arene_substitution_pattern.
• Stille_reaction wikiPageWikiLink Aryl.
• Stille_reaction wikiPageWikiLink Aryl_halide.
• Stille_reaction wikiPageWikiLink Associative_substitution.
• Stille_reaction wikiPageWikiLink Autocatalysis.
• Stille_reaction wikiPageWikiLink Benzophenone.
• Stille_reaction wikiPageWikiLink Benzyl.
• Stille_reaction wikiPageWikiLink Beta-Hydride_elimination.
• Stille_reaction wikiPageWikiLink Bite_angles.
• Stille_reaction wikiPageWikiLink Bromide.
• Stille_reaction wikiPageWikiLink Bromine.
• Stille_reaction wikiPageWikiLink Buchwald–Hartwig_amination.
• Stille_reaction wikiPageWikiLink By-product.
• Stille_reaction wikiPageWikiLink Caesium_fluoride.
• Stille_reaction wikiPageWikiLink Carbon_monoxide.
• Stille_reaction wikiPageWikiLink Carbonyl.
• Stille_reaction wikiPageWikiLink Catalysis.
• Stille_reaction wikiPageWikiLink Catalytic_cycle.
• Stille_reaction wikiPageWikiLink Category:Carbon-carbon_bond_forming_reactions.
• Stille_reaction wikiPageWikiLink Category:Name_reactions.
• Stille_reaction wikiPageWikiLink Category:Palladium.
• Stille_reaction wikiPageWikiLink Ceric_ammonium_nitrate.
• Stille_reaction wikiPageWikiLink Chemical_equilibrium.
• Stille_reaction wikiPageWikiLink Chemical_polarity.
• Stille_reaction wikiPageWikiLink Chemical_reaction.
• Stille_reaction wikiPageWikiLink Chemical_stability.
• Stille_reaction wikiPageWikiLink Chloride.
• Stille_reaction wikiPageWikiLink Chlorine.
• Stille_reaction wikiPageWikiLink Chromatography.
• Stille_reaction wikiPageWikiLink Cis–trans_isomerism.
• Stille_reaction wikiPageWikiLink Colin_Eaborn.
• Stille_reaction wikiPageWikiLink Cope_rearrangement.
• Stille_reaction wikiPageWikiLink Copper.
• Stille_reaction wikiPageWikiLink Copper(I)_iodide.
• Stille_reaction wikiPageWikiLink Coupling_reaction.
• Stille_reaction wikiPageWikiLink Cycloaddition.
• Stille_reaction wikiPageWikiLink Cytosine.
• Stille_reaction wikiPageWikiLink David_Milstein.
• Stille_reaction wikiPageWikiLink Density_functional_theory.
• Stille_reaction wikiPageWikiLink Diels–Alder_reaction.
• Stille_reaction wikiPageWikiLink Dimer_(chemistry).
• Stille_reaction wikiPageWikiLink Dipolar_bond.
• Stille_reaction wikiPageWikiLink Dissociative_substitution.
• Stille_reaction wikiPageWikiLink Ei-ichi_Negishi.
• Stille_reaction wikiPageWikiLink Electron_counting.
• Stille_reaction wikiPageWikiLink Electron_density.
• Stille_reaction wikiPageWikiLink Electronegativity.
• Stille_reaction wikiPageWikiLink Electrophile.
• Stille_reaction wikiPageWikiLink Electrophilic_aromatic_directing_groups.
• Stille_reaction wikiPageWikiLink Enantiomer.
• Stille_reaction wikiPageWikiLink Epoxide.
• Stille_reaction wikiPageWikiLink Ester.
• Stille_reaction wikiPageWikiLink Filtration.
• Stille_reaction wikiPageWikiLink Fluoride.
• Stille_reaction wikiPageWikiLink Free-radical_reaction.
• Stille_reaction wikiPageWikiLink Functional_group.
• Stille_reaction wikiPageWikiLink Furan.
• Stille_reaction wikiPageWikiLink Gilman_reagent.
• Stille_reaction wikiPageWikiLink Green_chemistry.
• Stille_reaction wikiPageWikiLink Grignard_reaction.
• Stille_reaction wikiPageWikiLink Halide.
• Stille_reaction wikiPageWikiLink Halocarbon.
• Stille_reaction wikiPageWikiLink Halogen.
• Stille_reaction wikiPageWikiLink Heck_reaction.
• Stille_reaction wikiPageWikiLink Heterocyclic_compound.
• Stille_reaction wikiPageWikiLink Hiyama_coupling.
• Stille_reaction wikiPageWikiLink Hydrofluoric_acid.
• Stille_reaction wikiPageWikiLink Hydrolysis.
• Stille_reaction wikiPageWikiLink Hypervalent_molecule.
• Stille_reaction wikiPageWikiLink Imidazole.
• Stille_reaction wikiPageWikiLink Indole.
• Stille_reaction wikiPageWikiLink Intramolecular_reaction.
• Stille_reaction wikiPageWikiLink Iodide.
• Stille_reaction wikiPageWikiLink Iodine.
• Stille_reaction wikiPageWikiLink Isomerization.
• Stille_reaction wikiPageWikiLink John_Kenneth_Stille.
• Stille_reaction wikiPageWikiLink Ketone.
• Stille_reaction wikiPageWikiLink Larry_E._Overman.

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