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

Philip C. Andrews; Anna C. Peatt; Colin L. Raston

doi:10.1016/j.tetlet.2003.10.188

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

Philip C. Andrews, Anna C. Peatt, Colin L. Raston

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

55 Citations (Scopus)

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 bis-allylated species via an iminium ion intermediate.

Original language	English
Pages (from-to)	243-248
Number of pages	6
Journal	Tetrahedron Letters
Volume	45
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2003.10.188
Publication status	Published - 5 Jan 2004
Externally published	Yes

Keywords

Aldehydes
Allylation
Gallium
Imines
Indium
Solvent free

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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 bis-allylated species via an iminium ion intermediate.",

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AU - Andrews, Philip C.

AU - Peatt, Anna C.

AU - Raston, Colin L.

PY - 2004/1/5

Y1 - 2004/1/5

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 bis-allylated species via an iminium ion intermediate.

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 bis-allylated species via an iminium ion intermediate.

KW - Aldehydes

KW - Allylation

KW - Gallium

KW - Imines

KW - Indium

KW - Solvent free

UR - http://www.scopus.com/inward/record.url?scp=0345735508&partnerID=8YFLogxK

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DO - 10.1016/j.tetlet.2003.10.188

M3 - Article

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SN - 0040-4039

VL - 45

SP - 243

EP - 248

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 2

ER -

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

Abstract

Keywords

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