Iron-Catalyzed Oxidative Arylmethylation of Activated Alkenes Using a Peroxide as the Methyl Source

Jian-Hong Fan; Ming-Bo Zhou; Yu Liu; Wen-Ting Wei; Xuan-Hui Ouyang; Ren-Jie Song; Jin-Heng Li

doi:10.1055/s-0033-1340665

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(5): 657-660
DOI: 10.1055/s-0033-1340665

letter

Iron-Catalyzed Oxidative Arylmethylation of Activated Alkenes Using a Peroxide as the Methyl Source

Authors

Jian-Hong Fan

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Fax: +86(731)88713642 eMail: jhli@hnu.edu.cn eMail: srj0731@hnu.edu.cn
Ming-Bo Zhou

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Fax: +86(731)88713642 eMail: jhli@hnu.edu.cn eMail: srj0731@hnu.edu.cn
Yu Liu

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Fax: +86(731)88713642 eMail: jhli@hnu.edu.cn eMail: srj0731@hnu.edu.cn
Wen-Ting Wei

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Fax: +86(731)88713642 eMail: jhli@hnu.edu.cn eMail: srj0731@hnu.edu.cn
Xuan-Hui Ouyang

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Fax: +86(731)88713642 eMail: jhli@hnu.edu.cn eMail: srj0731@hnu.edu.cn
Ren-Jie Song*

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Fax: +86(731)88713642 eMail: jhli@hnu.edu.cn eMail: srj0731@hnu.edu.cn
Jin-Heng Li*

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China Fax: +86(731)88713642 eMail: jhli@hnu.edu.cn eMail: srj0731@hnu.edu.cn

Abstract

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Abstract

A novel, simple route for the synthesis of oxindoles is presented via iron-catalyzed oxidative arylmethylation of activated alkenes with peroxides. This work is realized by the use of a peroxide as the methyl source and 1,4-diazabicyclo[2.2.2]octane as the ligand and represents a new access to oxindoles through an alkene oxidative difunctionalization process.

Key words

iron - alkenes - peroxides - difunctionalization - methylation - oxindoles

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Referenzen

References and Notes

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8 Typical Experimental Procedure for the Iron-Catalyzed Oxidative Arylmethylation of Alkenes with Peroxides To a Schlenk tube were added alkenes 1 (0.3 mmol), Fe(OAc)₂ (5 mol%), DABCO (10 mol%), DCP 2d (2 equiv), and DMSO (2 mL). Then the tube was charged with argon and was stirred at 120 °C (oil-bath temp) for the indicated time until complete consumption of starting material as monitored by TLC and GC–MS analysis. After the reaction was finished, the reaction mixture was cooled to r.t., diluted with EtOAc, and washed with brine. The aqueous phase was re-extracted with EtOAc. The combined organic extracts were dried over Na₂SO₄ and concentrated in vacuum, and the resulting residue was purified by silica gel column chromatography (hexane–EtOAc, 20:1) to afford the desired products 3. 3-Ethyl-1,3-dimethylindolin-2-one (3aa)^5d Yield 35.2 mg, 62%; yellow oil. ¹H NMR (400 MHz, CDCl₃): δ = 7.26 (t, J = 6.4 Hz, 1 H), 7.17 (d, J = 7.2 Hz, 1 H), 7.07 (t, J = 7.2 Hz, 1 H), 6.84 (d, J = 8.0 Hz, 1 H), 3.22 (s, 3 H), 1.97–1.89 (m, 1 H), 1.82–1.73 (m, 1 H), 1.35 (s, 3 H), 0.59 (t, J = 7.6 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 180.8, 143.5, 133.9, 127.6, 122.5, 122.4, 107.8, 48.9, 31.4, 26.0, 23.3, 8.8. IR (KBr): 1722, 1461 cm^–1. LRMS (EI, 70 eV): m/z (%) = 189 (21) [M⁺], 161 (100), 190 (6). ESI-HRMS: m/z calcd for C₁₂H₁₆NO [M + H]⁺: 190.1154; found: 190.1161.

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