t-BuONa-Mediated Transition-Metal-Free Autoxidation of Diarylmethanes to Ketones

Jiang-Sheng Li; Fan Yang; Qian Yang; Zhi-Wei Li; Guo-Qin Chen; Yu-Dong Da; Peng-Mian Huang; Chao Chen; Yuefei Zhang; Ling-Zhi Huang

doi:10.1055/s-0036-1588928

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(08): 994-998
DOI: 10.1055/s-0036-1588928

letter

t-BuONa-Mediated Transition-Metal-Free Autoxidation of Diarylmethanes to Ketones

Jiang-Sheng Li*

Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China eMail: jslichem@gmail.com eMail: jsli@csust.edu.cn

,

Fan Yang

Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China eMail: jslichem@gmail.com eMail: jsli@csust.edu.cn

,

Qian Yang

Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China eMail: jslichem@gmail.com eMail: jsli@csust.edu.cn

,

Zhi-Wei Li

Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China eMail: jslichem@gmail.com eMail: jsli@csust.edu.cn

,

Guo-Qin Chen

Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China eMail: jslichem@gmail.com eMail: jsli@csust.edu.cn

,

Yu-Dong Da

Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China eMail: jslichem@gmail.com eMail: jsli@csust.edu.cn

,

Peng-Mian Huang

Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China eMail: jslichem@gmail.com eMail: jsli@csust.edu.cn

,

Chao Chen

Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China eMail: jslichem@gmail.com eMail: jsli@csust.edu.cn

,

Yuefei Zhang

Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China eMail: jslichem@gmail.com eMail: jsli@csust.edu.cn

,

Ling-Zhi Huang

Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation, School of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410114, P. R. of China eMail: jslichem@gmail.com eMail: jsli@csust.edu.cn

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Abstract

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Abstract

Autoxidative sp³ C–H transformation of diarylmethanes has been demonstrated using O₂-mediation by t-BuONa. This protocol enables an alternative route for the access to diaryl ketones from benzyl derivatives in good to excellent yields under mild reaction conditions, without transition metal catalysts or additional chemical oxidants.

Key words

Ketones - benzyl derivatives - autoxidation - metal-free - oxygenation

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Referenzen

References and Notes

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16 Typical Procedure for t-BuONa-Mediated Autoxidation of Diarylmethanes to Ketones: To a predried 5-mL round-bottom flask diarylmethane 1a (0.4 mmol, 67 mg, 1 equiv), anhyd DMSO (0.4 mol/L), and t-BuONa (0.8 mmol, 77 mg, 2 equiv) were subsequently added as soon as possible. The reaction system was sealed by a rubber septum with a needle connected to an O₂ balloon, and then stirred at 50 °C for 1 h. During this period, the reaction system suffered complex color changes. The usual workup afforded the desired ketone 2a as a white solid (yield: 92%, 67 mg); mp 48–49 °C. ¹H NMR (400 MHz, CDCl₃): δ = 7.81 (d, J = 7.7 Hz, 4 H), 7.59 (t, J = 7.3 Hz, 2 H), 7.48 (t, J = 7.5 Hz, 4 H). ¹³C NMR (101 MHz, CDCl₃): δ = 196.8, 137.6 (2 × C), 132.4 (2 × C), 130.1 (4 × C), 128.3 (4 × C). EI–MS: m/z = 182.0 [M]⁺.

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