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Reactions of Aromatic Compounds
Reactions of Aromatic Compounds

... reaction is the formation of the cation intermediate Electron-donating substituents increase the rate of the substitution reactions by stabilizing the carbocation intermediate and the transition state leading to its formation ...
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... Processes such as P−C cleavage of phosphines, undesirable ligand dissociation, and irreversible ligand oxidative addition are well documented with many catalysts. Some of the pincer systems developed to date appear to avoid these pitfalls, perhaps due to their restrictive environments, at least unti ...
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14_chapter 8

... separation has the advantage of isolating the product by simple extraction with organic solvent. It was observed that the benzyl bromides of unsubstituted, substituted with electron donating groups undergo the reaction in shorter duration with maximum yield of benzaldehydes (entry 1,2), ...
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Stille reaction



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.
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