Formation of substituted 1-naphthols and related products via dimerization of alkyl 3-(o-halo(het)aryl)-oxopropanoates based on a CuI-catalyzed domino C-arylation/condensation/aromatization process

Heike Weischedel; Kavitha Sudheendran; Alevtina Mikhael; Jürgen Conrad; Wolfgang Frey; Uwe Beifuss

doi:10.1016/j.tet.2016.04.067

Formation of substituted 1-naphthols and related products via dimerization of alkyl 3-(o-halo(het)aryl)-oxopropanoates based on a CuI-catalyzed domino C-arylation/condensation/aromatization process

Heike Weischedel, Kavitha Sudheendran, Alevtina Mikhael, Jürgen Conrad, Wolfgang Frey, Uwe Beifuss

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

5 Scopus citations

Abstract

Substrates bearing both a β-ketoester moiety and a (het)aryl halide structure element were dimerized to 1-naphthols and related products in the presence of catalytic amounts of CuI in isopropanol. The reaction starts with an intermolecular C-arylation, which is followed by an intramolecular condensation. The final aromatization delivers the highly substituted products with yields up to 81%.

Original language	English
Pages (from-to)	3454-3467
Number of pages	14
Journal	Tetrahedron
Volume	72
Issue number	24
DOIs	https://doi.org/10.1016/j.tet.2016.04.067
State	Published - 16 Jun 2016
Externally published	Yes

Keywords

C-Arylation
Copper
Cross-coupling
Dimerization
Domino reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2016.04.067

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title = "Formation of substituted 1-naphthols and related products via dimerization of alkyl 3-(o-halo(het)aryl)-oxopropanoates based on a CuI-catalyzed domino C-arylation/condensation/aromatization process",

abstract = "Substrates bearing both a β-ketoester moiety and a (het)aryl halide structure element were dimerized to 1-naphthols and related products in the presence of catalytic amounts of CuI in isopropanol. The reaction starts with an intermolecular C-arylation, which is followed by an intramolecular condensation. The final aromatization delivers the highly substituted products with yields up to 81%.",

keywords = "C-Arylation, Copper, Cross-coupling, Dimerization, Domino reaction",

author = "Heike Weischedel and Kavitha Sudheendran and Alevtina Mikhael and J{\"u}rgen Conrad and Wolfgang Frey and Uwe Beifuss",

year = "2016",

month = jun,

day = "16",

doi = "10.1016/j.tet.2016.04.067",

language = "English",

volume = "72",

pages = "3454--3467",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "24",

}

Formation of substituted 1-naphthols and related products via dimerization of alkyl 3-(o-halo(het)aryl)-oxopropanoates based on a CuI-catalyzed domino C-arylation/condensation/aromatization process. / Weischedel, Heike; Sudheendran, Kavitha; Mikhael, Alevtina et al.
In: Tetrahedron, Vol. 72, No. 24, 16.06.2016, p. 3454-3467.

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

TY - JOUR

T1 - Formation of substituted 1-naphthols and related products via dimerization of alkyl 3-(o-halo(het)aryl)-oxopropanoates based on a CuI-catalyzed domino C-arylation/condensation/aromatization process

AU - Weischedel, Heike

AU - Sudheendran, Kavitha

AU - Mikhael, Alevtina

AU - Conrad, Jürgen

AU - Frey, Wolfgang

AU - Beifuss, Uwe

PY - 2016/6/16

Y1 - 2016/6/16

N2 - Substrates bearing both a β-ketoester moiety and a (het)aryl halide structure element were dimerized to 1-naphthols and related products in the presence of catalytic amounts of CuI in isopropanol. The reaction starts with an intermolecular C-arylation, which is followed by an intramolecular condensation. The final aromatization delivers the highly substituted products with yields up to 81%.

AB - Substrates bearing both a β-ketoester moiety and a (het)aryl halide structure element were dimerized to 1-naphthols and related products in the presence of catalytic amounts of CuI in isopropanol. The reaction starts with an intermolecular C-arylation, which is followed by an intramolecular condensation. The final aromatization delivers the highly substituted products with yields up to 81%.

KW - C-Arylation

KW - Copper

KW - Cross-coupling

KW - Dimerization

KW - Domino reaction

UR - http://www.scopus.com/inward/record.url?scp=84970960159&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2016.04.067

DO - 10.1016/j.tet.2016.04.067

M3 - Article

AN - SCOPUS:84970960159

SN - 0040-4020

VL - 72

SP - 3454

EP - 3467

JO - Tetrahedron

JF - Tetrahedron

IS - 24

ER -

Formation of substituted 1-naphthols and related products via dimerization of alkyl 3-(o-halo(het)aryl)-oxopropanoates based on a CuI-catalyzed domino C-arylation/condensation/aromatization process

Abstract

Keywords

ASJC Scopus subject areas

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