Indium/copper-mediated conjugate addition of unactivated alkyl iodides to α,β-unsaturated carbonyl compounds in water

Zhi Liang Shen; Hao Lun Cheong; Teck Peng Loh

doi:10.1016/j.tetlet.2008.12.079

Indium/copper-mediated conjugate addition of unactivated alkyl iodides to α,β-unsaturated carbonyl compounds in water

Zhi Liang Shen, Hao Lun Cheong, Teck Peng Loh

Nanyang Technological University

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

31 Scopus citations

Abstract

An efficient method for the conjugate addition of unactivated alkyl iodides to α,β-unsaturated carbonyl compounds using indium/copper in water is described. The reactions proceed more efficiently in water than in organic solvents. In, CuI, and InCl₃ are all essential for efficient reaction. Formation of a symmetrical vic-diarylalkane is observed when an aryl-substituted alkene is used as substrate.

Original language	English
Pages (from-to)	1051-1054
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2008.12.079
State	Published - 4 Mar 2009
Externally published	Yes

Keywords

Alkyl iodide
Conjugate addition
Copper
Indium
Water
α,β-Unsaturated carbonyl compounds

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10.1016/j.tetlet.2008.12.079

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abstract = "An efficient method for the conjugate addition of unactivated alkyl iodides to α,β-unsaturated carbonyl compounds using indium/copper in water is described. The reactions proceed more efficiently in water than in organic solvents. In, CuI, and InCl3 are all essential for efficient reaction. Formation of a symmetrical vic-diarylalkane is observed when an aryl-substituted alkene is used as substrate.",

keywords = "Alkyl iodide, Conjugate addition, Copper, Indium, Water, α,β-Unsaturated carbonyl compounds",

author = "Shen, {Zhi Liang} and Cheong, {Hao Lun} and Loh, {Teck Peng}",

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AU - Shen, Zhi Liang

AU - Cheong, Hao Lun

AU - Loh, Teck Peng

PY - 2009/3/4

Y1 - 2009/3/4

N2 - An efficient method for the conjugate addition of unactivated alkyl iodides to α,β-unsaturated carbonyl compounds using indium/copper in water is described. The reactions proceed more efficiently in water than in organic solvents. In, CuI, and InCl3 are all essential for efficient reaction. Formation of a symmetrical vic-diarylalkane is observed when an aryl-substituted alkene is used as substrate.

AB - An efficient method for the conjugate addition of unactivated alkyl iodides to α,β-unsaturated carbonyl compounds using indium/copper in water is described. The reactions proceed more efficiently in water than in organic solvents. In, CuI, and InCl3 are all essential for efficient reaction. Formation of a symmetrical vic-diarylalkane is observed when an aryl-substituted alkene is used as substrate.

KW - Alkyl iodide

KW - Conjugate addition

KW - Copper

KW - Indium

KW - Water

KW - α,β-Unsaturated carbonyl compounds

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DO - 10.1016/j.tetlet.2008.12.079

M3 - 文章

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SN - 0040-4039

VL - 50

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 9

ER -

Indium/copper-mediated conjugate addition of unactivated alkyl iodides to α,β-unsaturated carbonyl compounds in water

Abstract

Keywords

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