CAN-Catalyzed Rapid C–O Bond Formation towards α-Aminoxylation of 
Ketones

Peng Feng; Song Song; Li-He Zhang; Ning Jiao

doi:10.1055/s-0034-1379102

Synlett, Table of Contents

Synlett 2014; 25(19): 2717-2720
DOI: 10.1055/s-0034-1379102

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CAN-Catalyzed Rapid C–O Bond Formation towards α-Aminoxylation of Ketones

Authors

Peng Feng

^aState Key Laboratory of Natural and Biomimetic Drugs, Peking University, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China Fax: +86(10)82805297 Email: jiaoning@bjmu.edu.cn
Song Song

^aState Key Laboratory of Natural and Biomimetic Drugs, Peking University, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China Fax: +86(10)82805297 Email: jiaoning@bjmu.edu.cn
Li-He Zhang

^aState Key Laboratory of Natural and Biomimetic Drugs, Peking University, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China Fax: +86(10)82805297 Email: jiaoning@bjmu.edu.cn
Ning Jiao*

^aState Key Laboratory of Natural and Biomimetic Drugs, Peking University, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, P. R. of China Fax: +86(10)82805297 Email: jiaoning@bjmu.edu.cn

^bShanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai 200062, P. R. of China

Abstract

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Abstract

A simple and efficient approach towards α-oxyaminated ketones has been developed through CAN-catalyzed C–O bond formation with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). The environmentally friendly transformation is practical due to the use of commercial available catalyst, easy operating procedures, the broad substrate scope, and short reaction time.

Key words

CAN - ketone - α-aminoxylation - C–O bond formation - TEMPO

Full Text

References

References

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8 Typical Procedure for the Synthesis of 1,3-Diphenyl-2-[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]propane-1,3-dione (2a)^6b CAN (32.6 mg, 0.06 mmol), TEMPO (46.8 mg, 0.3 mmol), and 1a (67.2 mg, 0.3 mmol) in EtOAc (3.0 mL) was mixed under air. The mixture was stirred at 60 °C for 10–30 min using TLC detection with iodine. After cooling down and concentrating in vacuum, the residue was purified by flash chromatography on silica gel (eluent: PE–EtOAc, 30:1) to afford 102.5 mg (90%) of 2a. Analytical Data for Compound 2a Solid. ¹H NMR (400 MHz, CDCl₃): δ = 8.19 (d, J = 7.8 Hz, 4 H), 7.56–7.54 (m, 2 H), 7.53–7.43 (m, 4 H), 6.29 (s, 1 H), 1.48–1.38 (m, 6 H), 1.13 (s, 6 H), 0.95 (s, 6 H). ¹³C NMR (100 MHz, CDCl₃): δ = 195.0, 134.7, 133.7, 130.2, 128.4, 99.1, 60.2, 40.1, 32.9, 20.2, 17.0. MS (EI): m/z = 379.2 (100) [M]⁺.

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Supplementary Material

Supporting Information (PDF)