Rhenium-catalyzed synthesis of naphthalene derivatives via insertion of aldehydes into a C-H bond

Yoichiro Kuninobu, Yuta Nishina, Kazuhiko Takai

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

A rhenium complex, [ReBr(CO)3(THF)]2, catalyzed reactions of aromatic ketimines and aldehydes with dienophiles, followed by dehydration, to give naphthalene derivatives in good to excellent yields. This reaction proceeds via C-H bond activation, insertion of an aldehyde, intramolecular nucleophilic cyclization, reductive elimination, elimination of aniline and Diels-Alder reaction. After dehydration, naphthalene derivatives were formed.

Original languageEnglish
Pages (from-to)8463-8468
Number of pages6
JournalTetrahedron
Volume63
Issue number35
DOIs
Publication statusPublished - Aug 27 2007

Fingerprint

Rhenium
Dehydration
Aldehydes
Derivatives
Cyclization
Cycloaddition Reaction
Carbon Monoxide
Chemical activation
naphthalene
aniline
ketimine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Rhenium-catalyzed synthesis of naphthalene derivatives via insertion of aldehydes into a C-H bond. / Kuninobu, Yoichiro; Nishina, Yuta; Takai, Kazuhiko.

In: Tetrahedron, Vol. 63, No. 35, 27.08.2007, p. 8463-8468.

Research output: Contribution to journalArticle

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