Palladium(0)-catalyzed allylation of uracils and 2-thiouracils drastic effect of an aqueous reaction medium on the regioselectivity

Silvana Sigismondi; Denis Sinou; Montserrat Pérez; Marcial Moreno-Mañas; Roser Pleixats; Mercè Villarroya

doi:10.1016/0040-4039(94)88232-0

Palladium(0)-catalyzed allylation of uracils and 2-thiouracils drastic effect of an aqueous reaction medium on the regioselectivity

Silvana Sigismondi, Denis Sinou, Montserrat Pérez, Marcial Moreno-Mañas, Roser Pleixats, Mercè Villarroya

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

22 Citations (Scopus)

Abstract

Palladium(0)-catalyzed allylation of uracils in DMSO takes place at N-1 and at N-3. In sharp contrast, regiospecific allylation at N-1 is achieved in an organic-aqueous medium in the presence of palladium(II) acetate and the water-soluble sulfonated triphenylphosphine P(C 6 H 4 -m-SO 3 Na) 3 (tppts). Similar reactions with 2-thiouracils are also drastically dependent on the solvent, taking place at N-1 and N-3 (in dioxane) or at sulfur (organic-aqueous medium). Probably reactions in the organic-aqueous medium are kinetically controlled whereas allylations in DMSO or refluxing dioxane are thermodynamically controlled. © 1990.

Original language	English
Pages (from-to)	7085-7088
Journal	Tetrahedron Letters
Volume	35
Issue number	38
DOIs	https://doi.org/10.1016/0040-4039(94)88232-0
Publication status	Published - 19 Sep 1994

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10.1016/0040-4039(94)88232-0

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title = "Palladium(0)-catalyzed allylation of uracils and 2-thiouracils drastic effect of an aqueous reaction medium on the regioselectivity",

abstract = "Palladium(0)-catalyzed allylation of uracils in DMSO takes place at N-1 and at N-3. In sharp contrast, regiospecific allylation at N-1 is achieved in an organic-aqueous medium in the presence of palladium(II) acetate and the water-soluble sulfonated triphenylphosphine P(C 6 H 4 -m-SO 3 Na) 3 (tppts). Similar reactions with 2-thiouracils are also drastically dependent on the solvent, taking place at N-1 and N-3 (in dioxane) or at sulfur (organic-aqueous medium). Probably reactions in the organic-aqueous medium are kinetically controlled whereas allylations in DMSO or refluxing dioxane are thermodynamically controlled. {\textcopyright} 1990.",

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Palladium(0)-catalyzed allylation of uracils and 2-thiouracils drastic effect of an aqueous reaction medium on the regioselectivity. / Sigismondi, Silvana; Sinou, Denis; Pérez, Montserrat; Moreno-Mañas, Marcial; Pleixats, Roser; Villarroya, Mercè.

In: Tetrahedron Letters, Vol. 35, No. 38, 19.09.1994, p. 7085-7088.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Palladium(0)-catalyzed allylation of uracils and 2-thiouracils drastic effect of an aqueous reaction medium on the regioselectivity

AU - Sigismondi, Silvana

AU - Sinou, Denis

AU - Pérez, Montserrat

AU - Moreno-Mañas, Marcial

AU - Pleixats, Roser

AU - Villarroya, Mercè

PY - 1994/9/19

Y1 - 1994/9/19

N2 - Palladium(0)-catalyzed allylation of uracils in DMSO takes place at N-1 and at N-3. In sharp contrast, regiospecific allylation at N-1 is achieved in an organic-aqueous medium in the presence of palladium(II) acetate and the water-soluble sulfonated triphenylphosphine P(C 6 H 4 -m-SO 3 Na) 3 (tppts). Similar reactions with 2-thiouracils are also drastically dependent on the solvent, taking place at N-1 and N-3 (in dioxane) or at sulfur (organic-aqueous medium). Probably reactions in the organic-aqueous medium are kinetically controlled whereas allylations in DMSO or refluxing dioxane are thermodynamically controlled. © 1990.

AB - Palladium(0)-catalyzed allylation of uracils in DMSO takes place at N-1 and at N-3. In sharp contrast, regiospecific allylation at N-1 is achieved in an organic-aqueous medium in the presence of palladium(II) acetate and the water-soluble sulfonated triphenylphosphine P(C 6 H 4 -m-SO 3 Na) 3 (tppts). Similar reactions with 2-thiouracils are also drastically dependent on the solvent, taking place at N-1 and N-3 (in dioxane) or at sulfur (organic-aqueous medium). Probably reactions in the organic-aqueous medium are kinetically controlled whereas allylations in DMSO or refluxing dioxane are thermodynamically controlled. © 1990.

U2 - 10.1016/0040-4039(94)88232-0

DO - 10.1016/0040-4039(94)88232-0

M3 - Article

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SP - 7085

EP - 7088

IS - 38

ER -

Palladium(0)-catalyzed allylation of uracils and 2-thiouracils drastic effect of an aqueous reaction medium on the regioselectivity

Abstract

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