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

Sobi Asako; Seina Ishihara; Keiya Hirata; Kazuhiko Takai

doi:10.1021/jacs.9b05428

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 journal › Article

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 language	English
Pages (from-to)	9832-9836
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	141
Issue number	25
DOIs	https://doi.org/10.1021/jacs.9b05428
Publication status	Published - 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

Asako, S., Ishihara, S., Hirata, K., & Takai, K. (2019). Deoxygenative Insertion of Carbonyl Carbon into a C(sp³)-H Bond: Synthesis of Indolines and Indoles. Journal of the American Chemical Society, 141(25), 9832-9836. https://doi.org/10.1021/jacs.9b05428

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 journal › Article

Asako, S, Ishihara, S, Hirata, K & Takai, K 2019, 'Deoxygenative Insertion of Carbonyl Carbon into a C(sp³)-H Bond: Synthesis of Indolines and Indoles', Journal of the American Chemical Society, vol. 141, no. 25, pp. 9832-9836. https://doi.org/10.1021/jacs.9b05428

Asako S, Ishihara S, Hirata K, Takai K. Deoxygenative Insertion of Carbonyl Carbon into a C(sp³)-H Bond: Synthesis of Indolines and Indoles. Journal of the American Chemical Society. 2019 Jun 26;141(25):9832-9836. https://doi.org/10.1021/jacs.9b05428

Asako, Sobi ; Ishihara, Seina ; Hirata, Keiya ; Takai, Kazuhiko. / Deoxygenative Insertion of Carbonyl Carbon into a C(sp³)-H Bond : Synthesis of Indolines and Indoles. In: Journal of the American Chemical Society. 2019 ; Vol. 141, No. 25. pp. 9832-9836.

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10.1021/jacs.9b05428