Gallium metal mediated allylation of carbonyl compounds and imines under solvent-free conditions

P.C. Andrews; A.C. Peatt; Colin Raston

doi:10.1016/j.tetlet.2003.10.188

Gallium metal mediated allylation of carbonyl compounds and imines under solvent-free conditions

P.C. Andrews, A.C. Peatt, Colin Raston

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Abstract

Gallium metal is effective in mediating the allylation of various carbonyl compounds and imines under solvent-free conditions, with the application of sonic energy, affording the corresponding homoallylic alcohols and amines. The imines themselves were also prepared under solventless conditions in high yield, thereby establishing a two-step solvent-free synthesis of homoallylic amines. In comparison, indium metal produced a mixture of the desired homoallylic secondary amine and the bisallylated species via an iminium ion intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	243-248
Journal	Tetrahedron Letters
Volume	45
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2003.10.188
Publication status	Published - 2004

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title = "Gallium metal mediated allylation of carbonyl compounds and imines under solvent-free conditions",

abstract = "Gallium metal is effective in mediating the allylation of various carbonyl compounds and imines under solvent-free conditions, with the application of sonic energy, affording the corresponding homoallylic alcohols and amines. The imines themselves were also prepared under solventless conditions in high yield, thereby establishing a two-step solvent-free synthesis of homoallylic amines. In comparison, indium metal produced a mixture of the desired homoallylic secondary amine and the bisallylated species via an iminium ion intermediate. (C) 2003 Elsevier Ltd. All rights reserved.",

author = "P.C. Andrews and A.C. Peatt and Colin Raston",

year = "2004",

doi = "10.1016/j.tetlet.2003.10.188",

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T1 - Gallium metal mediated allylation of carbonyl compounds and imines under solvent-free conditions

AU - Andrews, P.C.

AU - Peatt, A.C.

AU - Raston, Colin

PY - 2004

Y1 - 2004

N2 - Gallium metal is effective in mediating the allylation of various carbonyl compounds and imines under solvent-free conditions, with the application of sonic energy, affording the corresponding homoallylic alcohols and amines. The imines themselves were also prepared under solventless conditions in high yield, thereby establishing a two-step solvent-free synthesis of homoallylic amines. In comparison, indium metal produced a mixture of the desired homoallylic secondary amine and the bisallylated species via an iminium ion intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

AB - Gallium metal is effective in mediating the allylation of various carbonyl compounds and imines under solvent-free conditions, with the application of sonic energy, affording the corresponding homoallylic alcohols and amines. The imines themselves were also prepared under solventless conditions in high yield, thereby establishing a two-step solvent-free synthesis of homoallylic amines. In comparison, indium metal produced a mixture of the desired homoallylic secondary amine and the bisallylated species via an iminium ion intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2003.10.188

DO - 10.1016/j.tetlet.2003.10.188

M3 - Article

VL - 45

SP - 243

EP - 248

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 2

ER -