Synlett, Table of Contents Synlett 2023; 34(01): 63-66DOI: 10.1055/a-1937-9185 letter Potassium Persulfate/Tributylamine-Mediated Alkylation/Annulation of N-Arylacrylamides with Alkyl Iodides Authors Huimin Chen Zetian Sun Hui Yang Fenghua Mao Xinhuan Yan Xiaoqing Li∗ Xiangsheng Xu∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract We report a catalyst-free method for the alkylation/annulation of N-arylacrylamides to give the corresponding 3-alkyl-2-oxo-2,3-dihydro-1H-indoles by using alkyl iodides as precursors of alkyl radicals. These reactions occur at moderate temperatures and are mediated by easily accessible K2S2O8 and Bu3N. Key words Key wordsarylacrylamides - cyclization - oxindoles - halogen-atom transfer - alkylation Full Text References References and Notes 1a Kiefer S, Mertz AC, Koryakina A, Hamburger M, Küenzi P. Eur. J. Pharm. 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Science 2020; 367: 1021 15 tert-Butyl 4-[(1,3-Dimethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)methyl]piperidine-1-carboxylate (3a); Typical Procedure A dried reaction tube charged with 1a (35 mg, 0.2 mmol), 2a (124.5 mg, 0.4mmol), and K2S2O8 (0.6 mmol) was evacuated and backfilled with argon three times. MeCN (1.6 mL), H2O (0.4 mL), and Bu3N (1 mmol) were injected into the tube by syringe, and the mixture was heated at 70 ℃ for 12 h. The crude product was purified by column chromatography [silica gel, PE–EtOAc (4:1)] to give a brown oil; yield: 55.4 mg (80%); Rf = 0.3 (PE–EtOAc, 4:1). 1H NMR (500 MHz, CDCl3): δ = 7.28 (d, J = 7.7 Hz, 1 H), 7.16 (d, J = 7.4 Hz, 1 H), 7.07 (t, J = 7.5 Hz, 1 H), 6.85 (d, J = 7.8 Hz, 1 H), 3.84 (s, 2 H), 3.22 (s, 3 H), 2.51–2.32 (m, 2 H), 1.98 (dd, J = 14.1, 6.2 Hz, 1 H), 1.76 (dd, J = 14.1, 5.4 Hz, 1 H), 1.39 (s, 9 H), 1.32 (s, 3 H), 1.25 (s, 1 H), 1.15–1.00 (m, 3 H), 0.91–0.83 (m, 1 H). 16 Li X, Xu X, Hu P, Xiao X, Zhou C. J. Org. Chem. 2013; 78: 7343 Supplementary Material Supplementary Material Supporting Information (PDF) (opens in new window)
