Facile Sc(OTf)3-catalyzed generation and successive aromatization of isobenzofuran from o -dicarbonylbenzenes

Yuta Nishina, Tatsuya Kida, Tomonari Ureshino

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Isobenzofuran can be prepared from o-phthalaldehyde using hydrosilane. The formed isobenzofuran is trapped by an alkene via a Diels-Alder reaction. Further dehydration proceeds to furnish the conjugated aromatic compound. This multistep reaction was promoted by catalytic amounts of Sc(OTf)3.

Original languageEnglish
Pages (from-to)3960-3963
Number of pages4
JournalOrganic Letters
Volume13
Issue number15
DOIs
Publication statusPublished - Aug 5 2011

Fingerprint

o-Phthalaldehyde
Aromatization
Diels-Alder reactions
aromatic compounds
Aromatic compounds
Cycloaddition Reaction
Alkenes
Dehydration
dehydration
alkenes
scandium triflate

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Facile Sc(OTf)3-catalyzed generation and successive aromatization of isobenzofuran from o -dicarbonylbenzenes. / Nishina, Yuta; Kida, Tatsuya; Ureshino, Tomonari.

In: Organic Letters, Vol. 13, No. 15, 05.08.2011, p. 3960-3963.

Research output: Contribution to journalArticle

@article{e19a3cd2414046fa9a5da8ecc2a2dd27,
title = "Facile Sc(OTf)3-catalyzed generation and successive aromatization of isobenzofuran from o -dicarbonylbenzenes",
abstract = "Isobenzofuran can be prepared from o-phthalaldehyde using hydrosilane. The formed isobenzofuran is trapped by an alkene via a Diels-Alder reaction. Further dehydration proceeds to furnish the conjugated aromatic compound. This multistep reaction was promoted by catalytic amounts of Sc(OTf)3.",
author = "Yuta Nishina and Tatsuya Kida and Tomonari Ureshino",
year = "2011",
month = "8",
day = "5",
doi = "10.1021/ol201479p",
language = "English",
volume = "13",
pages = "3960--3963",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "15",

}

TY - JOUR

T1 - Facile Sc(OTf)3-catalyzed generation and successive aromatization of isobenzofuran from o -dicarbonylbenzenes

AU - Nishina, Yuta

AU - Kida, Tatsuya

AU - Ureshino, Tomonari

PY - 2011/8/5

Y1 - 2011/8/5

N2 - Isobenzofuran can be prepared from o-phthalaldehyde using hydrosilane. The formed isobenzofuran is trapped by an alkene via a Diels-Alder reaction. Further dehydration proceeds to furnish the conjugated aromatic compound. This multistep reaction was promoted by catalytic amounts of Sc(OTf)3.

AB - Isobenzofuran can be prepared from o-phthalaldehyde using hydrosilane. The formed isobenzofuran is trapped by an alkene via a Diels-Alder reaction. Further dehydration proceeds to furnish the conjugated aromatic compound. This multistep reaction was promoted by catalytic amounts of Sc(OTf)3.

UR - http://www.scopus.com/inward/record.url?scp=79961034482&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79961034482&partnerID=8YFLogxK

U2 - 10.1021/ol201479p

DO - 10.1021/ol201479p

M3 - Article

VL - 13

SP - 3960

EP - 3963

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 15

ER -