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Synlett 2023; 34(20): 2525-2529
DOI: 10.1055/a-2158-8648
DOI: 10.1055/a-2158-8648
cluster
Special Issue Dedicated to Prof. Hisashi Yamamoto
Visible-Light-Induced Oxidative Generation of o-Quinone Methides for Inverse-Electron-Demand [4+2] Cycloaddition Reactions
This work was supported by the Tokuyama Science Foundation, the Takahashi Industrial and Economic Research Foundation, the Research Foundation for the Electrotechnology of Chubu, the Futaba Electronics Memorial Foundation, the Yashima Environment Technology Foundation, the Naohiko Fukuoka Memorial Foundation, the Japan Society for Bioscience, Biotechnology, and Agrochemistry, the Society of Iodine Science, the Japan Society for the Promotion of Science (JSPS KAKENHI, Grant JP 20K22537), and the Nakatsuji Fore-sight Foundation Research Grant. Funding for this research was also provided by Yokohama National University (kyodo kenkyu suishin program B).
Abstract
Organophotoredox-catalyzed oxidative generation of o-quinone methides (o-QMs) for inverse-electron-demand [4+2] cycloaddition reactions has been developed. One-electron oxidation of 2-(sulfanylmethyl)phenols by thioxanthylium photoredox catalyst generated o-QMs, which reacted with various styrenes to produce chromanes with high regioselectivity. This reaction offers a valuable approach for in situ generating o-QMs via one-electron oxidation process under irradiation with mild green light.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2158-8648.
- Supporting Information
Publication History
Received: 20 June 2023
Accepted after revision: 22 August 2023
Accepted Manuscript online:
22 August 2023
Article published online:
09 October 2023
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- 11 2,4-Diphenylchoroman (3a): Typical Procedure 2-(Sulfanylmethyl)phenol (1a, 58.3 mg, 0.20 mmol), styrene (2a, 62.5 mg, 0.60 mmol), TXT (5.0 mg, 9.0 μmol, 5.0 mol%), DCE (2.0 mL), and TFE (2.0 mL) were added into an 8 mL borosilicate vial. The resulting solution was stirred at room temperature under air and green LED irradiation for 24 h. The desired cycloadduct 3a was isolated by column chromatography on silica gel (hexane/ethyl acetate = 50:1). (2S*,4R*)- and (2R*,4R*)-2,4-Diphenylchromane (3a) White solid (42.4 mg, 74% yield). 1H NMR (500 MHz, CDCl3): δ = 7.52–7.48 (m, 2 H) (major), 7.42–7.38 (m, 2 H) (mixture), 7.37–7.29 (m, 8 H) (mixture), 7.29–7.19 (m, 6 H) (mixture), 7.17–7.12 (m, 2 H) (mixture), 7.02 (ddd, J = 14.1, 7.9, 1.5 Hz, 2 H) (minor), 6.97–6.95 (m, 1 H) (major), 6.90 (td, J = 7.4, 1.1 Hz, 1 H) (minor), 6.83–6.76 (m, 2 H) (major), 5.23 (dd, J = 11.2, 2.1 Hz, 1 H) (major), 5.05 (dd, J = 10.5, 2.3 Hz, 1 H) (minor), 4.37 (q, J = 6.1 Hz, 1 H) (major), 4.25 (q, J = 2.9 Hz, 1 H) (mixture), 2.51–2.46 (m, 1 H) (minor), 2.42 (ddd, J = 13.7, 5.7, 2.1 Hz, 1 H) (major), 2.33–2.24 (m, 1 H) (major). 13C{1H} NMR (126 MHz, CDCl3) (mixture): δ = 155.5, 155.4, 146.0, 144.5, 141.4, 141.2, 130.8, 129.8, 128.6, 128.6, 128.4, 128.1, 128.0, 127.7, 126.8, 126.4, 126.1, 126.0, 125.7, 123.1, 120.6, 120.5, 117.0, 117.0, 78.1, 73.2, 43.5, 40.6, 40.2, 38.3.
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- 13 See the Supporting Information.