Intramolecular photoredox reactions of 1,2-naphthoquinone derivatives

Yoshio Ando; Fumihiro Wakita; Ken Ohmori; Keisuke Suzuki

doi:10.1016/j.bmcl.2018.05.056

Intramolecular photoredox reactions of 1,2-naphthoquinone derivatives

Bioorg Med Chem Lett. 2018 Sep 1;28(16):2663-2666. doi: 10.1016/j.bmcl.2018.05.056. Epub 2018 May 30.

Authors

Yoshio Ando¹, Fumihiro Wakita², Ken Ohmori², Keisuke Suzuki²

Affiliations

¹ Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan. Electronic address: yando@chem.titech.ac.jp.
² Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan.

PMID: 29880402
DOI: 10.1016/j.bmcl.2018.05.056

Abstract

Photoirraditation of substituted 1,2-naphthoquinones gives the corresponding oxacycle via intramolecular redox reaction, which enabled net CH functionalization of the proximal position to the excited carbonyl group of the quinones. The substrate scope and mechanistic insights are described.

Keywords: 1,2-Naphthoquinone; CH functionalization; Photoreaction; Redox reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Heterocyclic Compounds, 3-Ring / chemical synthesis
Heterocyclic Compounds, 4 or More Rings / chemical synthesis
Light
Models, Chemical
Naphthoquinones / chemistry*
Naphthoquinones / radiation effects
Oxidation-Reduction
Photochemistry / methods

Substances

Heterocyclic Compounds, 3-Ring
Heterocyclic Compounds, 4 or More Rings
Naphthoquinones