Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes

Katalin Gulácsi, István Németh, Ádám Szappanos, Kinga Csillag, Tünde Zita Illyés, T. Kurtán, S. Antus

Research output: Contribution to journalArticle

Abstract

The Heck-oxyarylation of racemic 2-phenyl-2H-chromene [(±)-4b] and 1 2-dihydronaphthalenes (14a,b) has been studied with 2-chloromercuriphenols (5a-d) in the presence of Li2[PdCl4] catalyst The reactions resulted in the diastereoselective formation of racemic 6-phenylpterocarpans of (6R 6aR, 11aR) relative configuration [(±)-8a-d] and their dibenzo[1 3]dioxocine analogues [(±)-12a-d] as main products respectively The ratio of products and the lack of regioisomeric products (13a-d) corroborated the cationic mechanism of the oxyarylation of 2H-chromenes which has been also supported by the transformation of 14a,b under similar conditions.

Original languageEnglish
Pages (from-to)137-141
Number of pages5
JournalCroatica Chemica Acta
Volume86
Issue number2
DOIs
Publication statusPublished - Jul 2013

Fingerprint

Catalysts
5,7-dimethoxy-2-methyl-2H-benzopyran
1,2-dihydronaphthalene

Keywords

  • Catalysis
  • Dibenzo[d,g][1,3]dioxocines
  • Oxidative coupling
  • Palladium(0)
  • Pterocarpans
  • Reaction mechanism

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Gulácsi, K., Németh, I., Szappanos, Á., Csillag, K., Illyés, T. Z., Kurtán, T., & Antus, S. (2013). Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes. Croatica Chemica Acta, 86(2), 137-141. https://doi.org/10.5562/cca2103

Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes. / Gulácsi, Katalin; Németh, István; Szappanos, Ádám; Csillag, Kinga; Illyés, Tünde Zita; Kurtán, T.; Antus, S.

In: Croatica Chemica Acta, Vol. 86, No. 2, 07.2013, p. 137-141.

Research output: Contribution to journalArticle

Gulácsi, K, Németh, I, Szappanos, Á, Csillag, K, Illyés, TZ, Kurtán, T & Antus, S 2013, 'Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes', Croatica Chemica Acta, vol. 86, no. 2, pp. 137-141. https://doi.org/10.5562/cca2103
Gulácsi K, Németh I, Szappanos Á, Csillag K, Illyés TZ, Kurtán T et al. Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes. Croatica Chemica Acta. 2013 Jul;86(2):137-141. https://doi.org/10.5562/cca2103
Gulácsi, Katalin ; Németh, István ; Szappanos, Ádám ; Csillag, Kinga ; Illyés, Tünde Zita ; Kurtán, T. ; Antus, S. / Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes. In: Croatica Chemica Acta. 2013 ; Vol. 86, No. 2. pp. 137-141.
@article{5d42d7689c8044368a3329b186eec454,
title = "Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes",
abstract = "The Heck-oxyarylation of racemic 2-phenyl-2H-chromene [(±)-4b] and 1 2-dihydronaphthalenes (14a,b) has been studied with 2-chloromercuriphenols (5a-d) in the presence of Li2[PdCl4] catalyst The reactions resulted in the diastereoselective formation of racemic 6-phenylpterocarpans of (6R 6aR, 11aR) relative configuration [(±)-8a-d] and their dibenzo[1 3]dioxocine analogues [(±)-12a-d] as main products respectively The ratio of products and the lack of regioisomeric products (13a-d) corroborated the cationic mechanism of the oxyarylation of 2H-chromenes which has been also supported by the transformation of 14a,b under similar conditions.",
keywords = "Catalysis, Dibenzo[d,g][1,3]dioxocines, Oxidative coupling, Palladium(0), Pterocarpans, Reaction mechanism",
author = "Katalin Gul{\'a}csi and Istv{\'a}n N{\'e}meth and {\'A}d{\'a}m Szappanos and Kinga Csillag and Illy{\'e}s, {T{\"u}nde Zita} and T. Kurt{\'a}n and S. Antus",
year = "2013",
month = "7",
doi = "10.5562/cca2103",
language = "English",
volume = "86",
pages = "137--141",
journal = "Croatica Chemica Acta",
issn = "0011-1643",
publisher = "Croatian Chemical Society",
number = "2",

}

TY - JOUR

T1 - Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes

AU - Gulácsi, Katalin

AU - Németh, István

AU - Szappanos, Ádám

AU - Csillag, Kinga

AU - Illyés, Tünde Zita

AU - Kurtán, T.

AU - Antus, S.

PY - 2013/7

Y1 - 2013/7

N2 - The Heck-oxyarylation of racemic 2-phenyl-2H-chromene [(±)-4b] and 1 2-dihydronaphthalenes (14a,b) has been studied with 2-chloromercuriphenols (5a-d) in the presence of Li2[PdCl4] catalyst The reactions resulted in the diastereoselective formation of racemic 6-phenylpterocarpans of (6R 6aR, 11aR) relative configuration [(±)-8a-d] and their dibenzo[1 3]dioxocine analogues [(±)-12a-d] as main products respectively The ratio of products and the lack of regioisomeric products (13a-d) corroborated the cationic mechanism of the oxyarylation of 2H-chromenes which has been also supported by the transformation of 14a,b under similar conditions.

AB - The Heck-oxyarylation of racemic 2-phenyl-2H-chromene [(±)-4b] and 1 2-dihydronaphthalenes (14a,b) has been studied with 2-chloromercuriphenols (5a-d) in the presence of Li2[PdCl4] catalyst The reactions resulted in the diastereoselective formation of racemic 6-phenylpterocarpans of (6R 6aR, 11aR) relative configuration [(±)-8a-d] and their dibenzo[1 3]dioxocine analogues [(±)-12a-d] as main products respectively The ratio of products and the lack of regioisomeric products (13a-d) corroborated the cationic mechanism of the oxyarylation of 2H-chromenes which has been also supported by the transformation of 14a,b under similar conditions.

KW - Catalysis

KW - Dibenzo[d,g][1,3]dioxocines

KW - Oxidative coupling

KW - Palladium(0)

KW - Pterocarpans

KW - Reaction mechanism

UR - http://www.scopus.com/inward/record.url?scp=84886084166&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84886084166&partnerID=8YFLogxK

U2 - 10.5562/cca2103

DO - 10.5562/cca2103

M3 - Article

AN - SCOPUS:84886084166

VL - 86

SP - 137

EP - 141

JO - Croatica Chemica Acta

JF - Croatica Chemica Acta

SN - 0011-1643

IS - 2

ER -