Stille reaction

Summary

The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as organostannanes). A variety of organic electrophiles provide the other coupling partner. The Stille reaction is one of many palladium-catalyzed coupling reactions. : {\color{Blue}\ce{R^1-Sn(Alkyl)3}} + {\color{Red}\ce{R^2-X}} \ \ce{->[{\color{Green}\ce{Pd^0}}\text{ (catalytic)}][\text{ligand set}]} \ \overbrace{{\color{Blue}\ce{R^1}}!-!{\color{Red}\ce{R^2}}}^{coupled\ product} + {\color{Red}\ce{X}}!-!{\color{Blue}\ce{Sn(Alkyl)3}} :{\color{Blue}\ce{R^1}}!,\ {\color{Red}\ce{R^2}}: Allyl, alkenyl, aryl, benzyl,acyl :{\color{Red}\ce{X}}: halides (Cl, Br, I), pseudohalides (OTf, OPO(OR)2), OAc The R1 group attached to the trialkyltin is normally sp2-hybridized, including vinyl, and aryl

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Synthesis of C-(1->1) and C-(1->4)-Disaccharide Precursors via carbonylative Stille Coupling

Peter Steunenberg

DEA2000

Nitrile-functionalized pyrrolidinium ionic liquids as solvents for cross-coupling reactions involving in situ generated nanoparticle catalyst reservoirs

Ilaria Biondi, Manish Chaubey, Cinzia Chiappe, Yugang Cui, Paul Joseph Dyson, Zhaofu Fei, Christian Hartinger, Yuehui Li, Rosario Scopelliti, Xuemei Yang

Nitrile-functionalized pyrrolidinium-based ionic liqs. were prepd. and characterized by spectroscopic methods and x-ray crystallog. The application of these new ionic liqs. as reaction media for Suzuki and Stille C-C cross-coupling reactions was studied and compared with related imidazolium and pyridinium systems (including those with and without nitrile functionalities). The nature of the ionic liq. strongly influences the catalyzed reaction and it would appear that, in addn. to the nitrile group, the strength of anion-cation pairing in the ionic liq. and the viscosity of the ionic liq. play crit. roles. Nanoparticles are also detected following catalysis and their role, and the influence of the ionic liq. on them, is assessed. The ability to use the nitrile-functionalized pyrrolidinium-based ionic liqs. dild. in other (nonfunctionalized) ionic liqs. is also described.

Royal Society of Chemistry2010

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The Stille-coupling polymerization of a short conjugated polymer with an aliphatic linker was used to demonstrate a prototype in a new class of polymer semiconductors wherein the conjugation segment length and the length of the entire chain can be independently controlled. Subsequent thermal, morphological, and 2D grazing-incidence crystallographic analysis revealed this prototype polymer's ability to exhibit distinct thin-film morphologies without changing the molecular weight. In field-effect transistors this unique ability gave rise to an improvement of the charge carrier mobility from fibril-type (0.01 cm(2) V-1 s(-1)) to terrace morphologies (0.04 cm(2) V-1 s(-1)). When compared to a fully-conjugated, high molecular weight polymer, these differences afforded insight into the roles of inter-and intramolecular charge transport in the film, highlighting the importance of chain self-assembly on charge transport. Overall, our results indicate that employing linkers is a promising route to advance morphology control in semiconducting polymer based devices.

Royal Soc Chemistry2014