Synlett, Inhaltsverzeichnis Synlett 2016; 27(06): 956-960DOI: 10.1055/s-0035-1561290 letter © Georg Thieme Verlag Stuttgart · New York An Efficient Biomimetic Aerobic Oxidation of Alcohols Catalyzed by Iron Combined with Amino Acids Guofu Zhang a College of Chemical Engineering, Zhejiang University of Technology, 18 Chaowang Road, Hangzhou 310014, P. R. of China eMail: dingcr@zjut.edu.cn , Shasha Li a College of Chemical Engineering, Zhejiang University of Technology, 18 Chaowang Road, Hangzhou 310014, P. R. of China eMail: dingcr@zjut.edu.cn , Jie Lei a College of Chemical Engineering, Zhejiang University of Technology, 18 Chaowang Road, Hangzhou 310014, P. R. of China eMail: dingcr@zjut.edu.cn , Guihua Zhang a College of Chemical Engineering, Zhejiang University of Technology, 18 Chaowang Road, Hangzhou 310014, P. R. of China eMail: dingcr@zjut.edu.cn , Xiaoqiang Xie a College of Chemical Engineering, Zhejiang University of Technology, 18 Chaowang Road, Hangzhou 310014, P. R. of China eMail: dingcr@zjut.edu.cn , Chengrong Ding* a College of Chemical Engineering, Zhejiang University of Technology, 18 Chaowang Road, Hangzhou 310014, P. R. of China eMail: dingcr@zjut.edu.cn , Renhua Liu* b School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: liurh@ecust.edu.cn › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A novel combination of FeCl3, l-valine and TEMPO is found to oxidize alcohols to the carbonyl compounds with dioxygen. A wide range of primary/secondary benzyl, allylic, and heterocyclic alcohols have been efficiently converted into aldehydes and ketones with good to excellent isolated yields. Key words Key wordsalcohols - aldehydes - amino acids - iron - ketones - oxidation Volltext Referenzen References and Notes 1a Bäckvall E. Modern Oxidation Methods . Wiley-VCH; Weinheim: 2004 1b Tojo G, Fernandez M. 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After the reaction, the residue was filtered off, and the solvent was removed under vacuum to give the crude product, which was purified by column chromatography on silica gel to give the pure product 1 (0.1093 g isolated yield 91%). 1H NMR (500 MHz, CDCl3): δ = 2.38 (s, 3 H), 7.27 (d, J = 4.3 Hz, 2 H), 7.73 (d, J = 4.0 Hz, 2 H), 9.91 (s, 1 H). 13C NMR (125 MHz, CDCl3): δ = 21.5, 129.4, 129.5, 134.0, 145.2, 191.6. 26 Typical Procedure for Secondary Alcohol Oxidation (1-Phenethyl Alcohol) A mixture of 1-phenethyl alcohol (0.1222 g, 1.0 mmol), l-valine (0.0117 g, 0.1 mmol), FeCl3 (0.0162 g, 0.1 mmol), TEMPO (0.0156 g, 0.1 mmol), toluene (4.0 mL), 4 Å MS (0.7000 g) were added to a 150 mL Schlenk tube. Then the resulting mixture was vigorously stirred under oxygen at reflux temperature for 24 h. After the reaction, the residue was filtered off, and the solvent was removed under vacuum to give the crude product, which was purified by column chromatography on silica gel to give the pure product 26 (0.1093 g isolated yield 91%). 1H NMR (500 MHz, CDCl3): δ = 2.52 (s, 3 H), 7.40 (t, J = 7.5 Hz, 2 H), 7.51 (t, J = 7.0 Hz, 1 H), 7.91 (d, J = 4.3 Hz, 2 H). 13C NMR (125 MHz, CDCl3): δ = 26.5, 128.2, 128.5, 133.0, 137.1, 198.1. Zusatzmaterial Zusatzmaterial Supporting Information
