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^*

^*Corresponding author for this work

Nanyang Technological University

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

31 Citations (Scopus)

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
Publication status	Published - Mar 4 2009
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

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

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

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 - α,β-Unsaturated carbonyl compounds

KW - Alkyl iodide

KW - Conjugate addition

KW - Copper

KW - Indium

KW - Water

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VL - 50

SP - 1051

EP - 1054

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

ASJC Scopus Subject Areas

Keywords

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