Stille reaction

Stille reaction
Named after	John Kenneth Stille
Reaction type	Coupling reaction
Identifiers
Organic Chemistry Portal	stille-coupling
RSC ontology ID	RXNO:0000035

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]

{\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 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
^ ^a ^b Stille, 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.
^ Cordova, C.; Bartolomé, C.; Martínez-Ilarduya, J.M..; Espinet, P. ACS Catal., 2015, 5, 3040–3053.(doi:10.1021/acscatal.5b00448).

[Hartwig-1] Hartwig, J. F. Organotransition Metal Chemistry, from Bonding to Catalysis; University Science Books: New York, 2010. ISBN 189138953X

[name99-2] Stille, J. K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508–524. (Review)

[name98-3] Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1998, 50, 1–652. (Review)

[name59-4] Scott, W. J.; Crisp, G. T.; Stille, J. K. Organic Syntheses, Coll. Vol. 8, p. 97 (1993); Vol. 68, p. 116 (1990). (Article)

[name58-5] 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)

[name12-6] Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier: Burlington, 2005.

[name70-7] Mitchell, T. N. J. Organomet. Chem., 1986, 304, 1–16.

[name8-8] Mitchell, T. N. Synthesis, 1992, 803–815. (doi:10.1055/s-1992-26230)

[name24-9] Farina, V. Pure Appl. Chem., 1996, 68, 73–78. (doi:10.1351/pac199668010073).

[name28-10] Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: Online, 2004. (doi:10.1002/0471264180.or050.01).

[name9-11] Espinet, P.; Echavarren, A. M. Angew. Chem. Int. Ed., 2004, 43, 4704–4734.(doi:10.1002/anie.200300638)

[name71-12] Pattenden, G.; Sinclair, D. J. J.Organomet. Chem., 2002, 653, 261–268.

[name72-13] Kosugi, M.; Fugami, K. J. Organomet. Chem., 2002, 19, 10–16.

[name73-14] Pierre Genet, J.; Savignac, M. J. Organomet. Chem., 1999, 576, 305–317.

[name74-15] Cordova, C.; Bartolomé, C.; Martínez-Ilarduya, J.M..; Espinet, P. ACS Catal., 2015, 5, 3040–3053.(doi:10.1021/acscatal.5b00448).

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