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.[1][2][3]
The R1 group attached to the trialkyltin is normally sp2-hybridized, including vinyl, and aryl groups.
These organostannanes are also stable to both air and moisture, and many of these reagents either are 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, or I, yet pseudohalides such as triflates and sulfonates and phosphates can also be used.[4][5] Several reviews have been published.[6][2][7][8][9][10][11][12][13][14][15][excessive citations]
^Hartwig, J. F. Organotransition Metal Chemistry, from Bonding to Catalysis; University Science Books: New York, 2010. ISBN 189138953X
^ abStille, J. K. Angew. Chem. Int. Ed. Engl.1986, 25, 508–524. (Review)
^Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React.1998, 50, 1–652. (Review)
^Scott, W. J.; Crisp, G. T.; Stille, J. K. Organic Syntheses, Coll. Vol. 8, p. 97 (1993); Vol. 68, p. 116 (1990). (Article)
^Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Organic Syntheses, Coll. Vol. 9, p. 553 (1998); Vol. 71, p. 97 (1993). (Article)
^Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier: Burlington, 2005.
^Mitchell, T. N. J. Organomet. Chem., 1986, 304, 1–16.
^Mitchell, T. N. Synthesis, 1992, 803–815. (doi:10.1055/s-1992-26230)
^Farina, V. Pure Appl. Chem., 1996, 68, 73–78. (doi:10.1351/pac199668010073).
^Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: Online, 2004. (doi:10.1002/0471264180.or050.01).
^Espinet, P.; Echavarren, A. M. Angew. Chem. Int. Ed., 2004, 43, 4704–4734.(doi:10.1002/anie.200300638)
^Pattenden, G.; Sinclair, D. J. J.Organomet. Chem., 2002, 653, 261–268.
^Kosugi, M.; Fugami, K. J. Organomet. Chem., 2002, 19, 10–16.
^Pierre Genet, J.; Savignac, M. J. Organomet. Chem., 1999, 576, 305–317.
The Stillereaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is...
John Kenneth Stille (May 8, 1930 – July 19, 1989) was an American chemist who discovered the Stillereaction. He received B.A. and M.A. degrees from the...
Stille reactionStille Omgang, a religious procession in the Netherlands Stille Hilfe, an aid organization for SS members after WWII "Die Stille" (the...
Palladium on carbon is also used for coupling reactions. Examples include the Suzuki reaction and Stillereaction. A solution of palladium chloride and hydrochloric...
cross-coupling reaction is being used. Stillereactions use tin, Suzuki reactions use boron, Sonogashira reactions use copper, and Negishi reactions use zinc...
air-stable solid. It is used as a source of vinyl anion equivalent in Stille coupling reactions. As a source of vinyltin reagents, early work used vinyl trimethyltin...
Vittorio; Krishnamurthy, Venkat; Scott, William J. (1997). "The StilleReaction". Organic Reactions. pp. 1–652. doi:10.1002/0471264180.or050.01. ISBN 0471264180...
Vittorio; Krishnamurthy, Venkat; Scott, William J. (1997). "The StilleReaction". Organic Reactions. pp. 1–652. doi:10.1002/0471264180.or050.01. ISBN 0-471-26418-0...
chloride finds some use in organic synthesis, e.g., as an additive in the Stillereaction. Also, in biochemical applications, it can be used to precipitate RNA...
carbon-carbon forming reactions in transition-metal catalyzed cross-coupling reactions, such as Stillereaction, Heck reaction, Sonogashira coupling,...
methods. Despite the subsequent development of alternative reactions (Suzuki, Sonogashira, Stille, Hiyama, Negishi), the Kumada coupling continues to be employed...
chloride. Perilla ketone has also been prepared in 74% yield via the Stillereaction from a 3-furyl-organotin compound and isocaproyl chloride in tetrahydrofuran...
organic chemistry, a coupling reaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid of a...
of fine chemicals. Prominent coupling reactions include the Heck, Suzuki, Sonogashira coupling, Stillereactions, and the Kumada coupling. Palladium(II)...
of hydroxide-chlorides. It can be used in place of palladium in the Stillereaction, which couples two carbon atoms using an organotin compound. It can...
removed with Raney nickel. Organotellurium(IV) compounds participate in Stillereactions: Telluroxides are generally related to sulfoxides and selenoxides in...
trialkylstannane 2 which was then coupled with an aryl iodide 1 in a Stillereaction in presence of carbon monoxide (tris(dibenzylideneacetone)dipalladium(0)...
particularly useful, especially when compared to the aforementioned Stille and Suzuki coupling reactions. The major drawback of the Negishi coupling, aside from its...
Global Information![{\displaystyle {\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}}}}](https://wikimedia.org/api/rest_v1/media/math/render/svg/5baabb66db61c2d31fa2a5ca2b4e8156ee7c4133 "General scheme of the Stille reaction")
