Deoxygenative Insertion of Carbonyl Carbon into a C(sp3)-H Bond: Synthesis of Indolines and Indoles

Sobi Asako, Seina Ishihara, Keiya Hirata, Kazuhiko Takai

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A simple deoxygenation reagent prepared in situ from commercially available Mo(CO)6 and ortho-quinone has been developed for the synthesis of indoline and indole derivatives. The Mo/quinone complex efficiently deoxygenates carbonyl compounds bearing a neighboring dialkylamino group and effects intramolecular cyclizations with the insertion of a deoxygenated carbonyl carbon into a C(sp3)-H bond, in which a carbonyl group acts as a carbene equivalent. The reaction also proceeds with a catalytic amount of Mo/quinone in the presence of disilane as an oxygen atom acceptor.

Original languageEnglish
Pages (from-to)9832-9836
Number of pages5
JournalJournal of the American Chemical Society
Volume141
Issue number25
DOIs
Publication statusPublished - Jun 26 2019

Fingerprint

Bearings (structural)
Indoles
Carbonyl compounds
Cyclization
Carbon
Derivatives
Atoms
Oxygen
indoline
benzoquinone

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Deoxygenative Insertion of Carbonyl Carbon into a C(sp3)-H Bond : Synthesis of Indolines and Indoles. / Asako, Sobi; Ishihara, Seina; Hirata, Keiya; Takai, Kazuhiko.

In: Journal of the American Chemical Society, Vol. 141, No. 25, 26.06.2019, p. 9832-9836.

Research output: Contribution to journalArticle

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