Synthesis of indenes by ytterbium-catalyzed carboalkoxylation/Friedel- Crafts reaction of arylidenecyclopropanes with acetals

Itaru Nakamura; Michiru Kamada; Yoshinori Yamamoto

doi:10.1016/j.tetlet.2004.02.066

Synthesis of indenes by ytterbium-catalyzed carboalkoxylation/Friedel- Crafts reaction of arylidenecyclopropanes with acetals

Itaru Nakamura, Michiru Kamada, Yoshinori Yamamoto

SCI - Research and Analytical Center for Giant Molecules

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

31 Citations (Scopus)

Abstract

Ytterbium-catalyzed tandem carboalkoxylation/Friedel-Crafts reaction of arylidenecyclopropanes 1 with acetals 2 afforded the corresponding indene derivatives 3 in good to high yields. For example, in the presence of 10mol% of Yb(OTf)₃ the reaction of 1-phenylbenzylidenecyclopropane 1a with the dimethyl acetals of benzaldehyde 2a, p-tolualdehyde 2b, and p-anisaldehyde 2c gave 1,3-diphenyl-2-(2-methoxyethyl)indene 3a, 2-(2-methoxyethyl)-3-phenyl-1-(p- tolyl)indene 3b, and 1-(p-anisyl)-2-(2-methoxyethyl)-3-phenylindene 3c in 82%, 80%, and 80% yields, respectively.

Original language	English
Pages (from-to)	2903-2906
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	14
DOIs	https://doi.org/10.1016/j.tetlet.2004.02.066
Publication status	Published - 2004 Mar 29

Keywords

Carboalkoxylation
Friedel-Craft reaction
Indene
Lewis acid catalysis
Ytterbium catalyzed reaction
Ytterbium triflate
exo-Methylenecyclopropane

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis of indenes by ytterbium-catalyzed carboalkoxylation/Friedel- Crafts reaction of arylidenecyclopropanes with acetals",

abstract = "Ytterbium-catalyzed tandem carboalkoxylation/Friedel-Crafts reaction of arylidenecyclopropanes 1 with acetals 2 afforded the corresponding indene derivatives 3 in good to high yields. For example, in the presence of 10mol% of Yb(OTf)3 the reaction of 1-phenylbenzylidenecyclopropane 1a with the dimethyl acetals of benzaldehyde 2a, p-tolualdehyde 2b, and p-anisaldehyde 2c gave 1,3-diphenyl-2-(2-methoxyethyl)indene 3a, 2-(2-methoxyethyl)-3-phenyl-1-(p- tolyl)indene 3b, and 1-(p-anisyl)-2-(2-methoxyethyl)-3-phenylindene 3c in 82%, 80%, and 80% yields, respectively.",

keywords = "Carboalkoxylation, Friedel-Craft reaction, Indene, Lewis acid catalysis, Ytterbium catalyzed reaction, Ytterbium triflate, exo-Methylenecyclopropane",

author = "Itaru Nakamura and Michiru Kamada and Yoshinori Yamamoto",

year = "2004",

month = mar,

day = "29",

doi = "10.1016/j.tetlet.2004.02.066",

language = "English",

volume = "45",

pages = "2903--2906",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "14",

}

TY - JOUR

T1 - Synthesis of indenes by ytterbium-catalyzed carboalkoxylation/Friedel- Crafts reaction of arylidenecyclopropanes with acetals

AU - Nakamura, Itaru

AU - Kamada, Michiru

AU - Yamamoto, Yoshinori

PY - 2004/3/29

Y1 - 2004/3/29

N2 - Ytterbium-catalyzed tandem carboalkoxylation/Friedel-Crafts reaction of arylidenecyclopropanes 1 with acetals 2 afforded the corresponding indene derivatives 3 in good to high yields. For example, in the presence of 10mol% of Yb(OTf)3 the reaction of 1-phenylbenzylidenecyclopropane 1a with the dimethyl acetals of benzaldehyde 2a, p-tolualdehyde 2b, and p-anisaldehyde 2c gave 1,3-diphenyl-2-(2-methoxyethyl)indene 3a, 2-(2-methoxyethyl)-3-phenyl-1-(p- tolyl)indene 3b, and 1-(p-anisyl)-2-(2-methoxyethyl)-3-phenylindene 3c in 82%, 80%, and 80% yields, respectively.

AB - Ytterbium-catalyzed tandem carboalkoxylation/Friedel-Crafts reaction of arylidenecyclopropanes 1 with acetals 2 afforded the corresponding indene derivatives 3 in good to high yields. For example, in the presence of 10mol% of Yb(OTf)3 the reaction of 1-phenylbenzylidenecyclopropane 1a with the dimethyl acetals of benzaldehyde 2a, p-tolualdehyde 2b, and p-anisaldehyde 2c gave 1,3-diphenyl-2-(2-methoxyethyl)indene 3a, 2-(2-methoxyethyl)-3-phenyl-1-(p- tolyl)indene 3b, and 1-(p-anisyl)-2-(2-methoxyethyl)-3-phenylindene 3c in 82%, 80%, and 80% yields, respectively.

KW - Carboalkoxylation

KW - Friedel-Craft reaction

KW - Indene

KW - Lewis acid catalysis

KW - Ytterbium catalyzed reaction

KW - Ytterbium triflate

KW - exo-Methylenecyclopropane

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U2 - 10.1016/j.tetlet.2004.02.066

DO - 10.1016/j.tetlet.2004.02.066

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VL - 45

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EP - 2906

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 14

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