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Synlett 2017; 28(09): 1040-1045
DOI: 10.1055/s-0036-1589001
DOI: 10.1055/s-0036-1589001
letter
Intramolecular Photoredox Reaction of Naphthoquinone Derivatives
Supported by: Japan Society for the Promotion of Science (JSPS) Grant-in-Aid for Scientific Research (S) (16H06351)Supported by: Japan Society for the Promotion of Science (JSPS) Grant-in-Aid for Young Scientists (B) (26810018)
Further Information
Publication History
Received: 24 February 2017
Accepted after revision: 22 March 2017
Publication Date:
19 April 2017 (online)
Abstract
Photoinduced intramolecular redox reaction of naphthoquinone derivatives is described, enabling C–H bond oxygenation at the α-position of the quinone nucleus and the quinone reduction under photoirradiation. The substrate scope and mechanistic insight are reported.
Key words
naphthoquinone - photochemistry - redox reaction - cyclization - C–H bond functionalizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589001.
- Supporting Information
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References and Notes
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For photoinduced degradation of the pluramycins, see:
For photoreactions of quinones in the presence of O2, see:
For related photoredox reactions of anthraquinones with electron transfer, see:
For a review, see:
-
20
This result may be no wonder in view of that the ring opening of cyclopropylmethyl radical with a phenyl group is reversible in favor of the closed form (Scheme 7):