The Michael Addition of Indole to α,β-Unsaturated Ketones Catalyzed by Iodine at Room Temperature

Shun Yi Wang; Shun Jun Ji; Teck Peng Loh

doi:10.1055/s-2003-42105

The Michael Addition of Indole to α,β-Unsaturated Ketones Catalyzed by Iodine at Room Temperature

Shun Yi Wang, Shun Jun Ji^*, Teck Peng Loh

^*Corresponding author for this work

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

124 Citations (Scopus)

Abstract

Indole undergoes conjugate addition with α,β-unsaturated ketones by means of alkylation of indole in the presence of a catalytic amount of molecular I₂ at room temperature to afford the corresponding adduct in excellent yields (up to 96%). The substitution on the indole nucleus occurred exclusively at the 3-position. N-alkylation products have not been observed.

Original language	English
Pages (from-to)	2377-2379
Number of pages	3
Journal	Synlett
Issue number	15
DOIs	https://doi.org/10.1055/s-2003-42105
Publication status	Published - 2003
Externally published	Yes

ASJC Scopus Subject Areas

Organic Chemistry

Keywords

Indoles
Michael reaction
Molecular iodine

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10.1055/s-2003-42105

Cite this

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title = "The Michael Addition of Indole to α,β-Unsaturated Ketones Catalyzed by Iodine at Room Temperature",

abstract = "Indole undergoes conjugate addition with α,β-unsaturated ketones by means of alkylation of indole in the presence of a catalytic amount of molecular I2 at room temperature to afford the corresponding adduct in excellent yields (up to 96%). The substitution on the indole nucleus occurred exclusively at the 3-position. N-alkylation products have not been observed.",

keywords = "Indoles, Michael reaction, Molecular iodine",

author = "Wang, {Shun Yi} and Ji, {Shun Jun} and Loh, {Teck Peng}",

year = "2003",

doi = "10.1055/s-2003-42105",

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AU - Wang, Shun Yi

AU - Ji, Shun Jun

AU - Loh, Teck Peng

PY - 2003

Y1 - 2003

N2 - Indole undergoes conjugate addition with α,β-unsaturated ketones by means of alkylation of indole in the presence of a catalytic amount of molecular I2 at room temperature to afford the corresponding adduct in excellent yields (up to 96%). The substitution on the indole nucleus occurred exclusively at the 3-position. N-alkylation products have not been observed.

AB - Indole undergoes conjugate addition with α,β-unsaturated ketones by means of alkylation of indole in the presence of a catalytic amount of molecular I2 at room temperature to afford the corresponding adduct in excellent yields (up to 96%). The substitution on the indole nucleus occurred exclusively at the 3-position. N-alkylation products have not been observed.

KW - Indoles

KW - Michael reaction

KW - Molecular iodine

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DO - 10.1055/s-2003-42105

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JO - Synlett

JF - Synlett

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ER -

The Michael Addition of Indole to α,β-Unsaturated Ketones Catalyzed by Iodine at Room Temperature

Abstract

ASJC Scopus Subject Areas

Keywords

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