Visible-Light-Induced Oxidative Generation of o-Quinone Methides for Inverse-Electron-Demand [4+2] Cycloaddition Reactions

Shoya Nohara; Suguru Iwai; Naoya Yamaguchi; Yosuke Asada; Yusuke Kamiyama; Yuta Tanaka; Kenta Tanaka; Yujiro Hoshino

doi:10.1055/a-2158-8648

Synlett, Inhaltsverzeichnis

Synlett 2023; 34(20): 2525-2529
DOI: 10.1055/a-2158-8648

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Special Issue Dedicated to Prof. Hisashi Yamamoto

Visible-Light-Induced Oxidative Generation of o-Quinone Methides for Inverse-Electron-Demand [4+2] Cycloaddition Reactions

Shoya Nohara

^aGraduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan

,

Suguru Iwai

^aGraduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan

,

Naoya Yamaguchi

^aGraduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan

,

Yosuke Asada

^aGraduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan

,

Yusuke Kamiyama

^aGraduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan

,

Yuta Tanaka

^aGraduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan

,

Kenta Tanaka∗

^bResearch Institute for Interdisciplinary Science, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan

,

Yujiro Hoshino∗

^aGraduate School of Environment and Information Sciences, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan

› Institutsangaben

Abstract

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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.

Key words

o-quinone methide - photoredox - visible light - chromane - [4+2] cycloaddition

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Referenzen

References and Notes

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9 Since it was difficult to separate the diastereomers in our system, the diastereomeric ratio of 3 was determined by ¹H NMR analysis comparing the benzylic peaks at the C2 position of chroman. Each of the diastereomers of 3a was confirmed by comparison with the spectral data described in the literature, see: Pagar VV, Tseng C.-C, Liu R.-S. Chem. Eur. J. 2014; 20: 10519
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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.
12 Lyu J, Claraz A, Vitale MR, Allain C, Masson G. J. Org. Chem. 2020; 85: 12843
13 See the Supporting Information.

Zusatzmaterial

Supporting Information