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Synlett 2016; 27(03): 427-431
DOI: 10.1055/s-0035-1560830
DOI: 10.1055/s-0035-1560830
letter
Iron-Catalyzed Oxidative Sulfonylation of Enol Acetates: An Environmentally Benign Approach to β-Keto Sulfones
Further Information
Publication History
Received: 26 August 2015
Accepted after revision: 05 October 2015
Publication Date:
18 November 2015 (online)
Abstract
The first application of iron-catalyzed sulfonylation of aryl enol acetates with sulfonyl hydrazides for the construction of β-keto sulfones under aerobic conditions is reported. The present protocol, which utilizes an inexpensive iron salt as the catalyst, readily available sulfonyl hydrazides as the sulfonylating reagents, and air as oxidant under mild conditions, provides a cost-effective and environmentally benign approach to various β-keto sulfones.
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- 22 General Procedure for the Synthesis of β-Keto Sulfones 3 Enol acetate 1 (1 mmol), sulfonyl hydrazide 2 (1.5 mmol), FeCl3 (10 mol%), and THF (3 mL) were added to a flask open to the air, and the mixture was stirred at 70 °C for 5–6 h (Scheme 2). After completion of the reaction (monitoring by TLC), H2O (5 mL) was added, and the mixture was extracted with EtOAc (3 × 5 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography using a mixture of hexane–EtOAc (4:1) as eluent to afford an analytically pure sample of product 3. All the compounds 3 are known and were characterized by comparison of their spectroscopic data with those reported in the literature.4d,5b,19d,21 Characterization Data of Representative Compounds 3 Compound 3a:4d,5b solid; 91% yield. 1H NMR (400 MHz, CDCl3): δ = 7.95 (d, J = 7.6 Hz, 2 H), 7.80 (t, J = 8.5 Hz, 2 H), 7.61 (t, J = 7.5 Hz, 1 H), 7.44 (t, J = 7.8 Hz, 2 H), 7.35 (d, J = 7.8 Hz, 2 H), 4.71 (s, 2 H), 2.47 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 188.27, 145.53, 135.85, 135.84, 134.43, 129.98, 129.46, 128.96, 128.73, 63.86, 21.87. MS (EI): m/z = 274 [M+]. Anal. Calcd for C15H14O3S: C, 65.67; H, 5.14; S, 11.69. Found: C, 65.89; H, 4.93; S, 11.53. Compound 3i:19d,21b solid; 92% yield. 1H NMR (400 MHz, CDCl3): δ = 7.86 (d, J = 8.4 Hz, 2 H), 7.81 (d, J = 8.4 Hz, 2 H), 7.30–7.26 (m, 2 H), 7.24–7.20 (m, 2 H), 4.70 (s, 2 H), 2.44 (s, 3 H), 2.44 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 187.65, 145.38, 145.15, 136.11, 133.46, 129.70, 129.39, 129.37, 128.50, 63.56, 21.59, 21.52. MS (EI): m/z = 288 [M+]. Anal. Calcd for C16H16O3S: C, 66.64; H, 5.59; S, 11.12. Found: C, 66.80; H, 5.43; S, 11.39. Compound 3j: 4d,21a solid; 86% yield. 1H NMR (400 MHz, CDCl3): δ = 7.91–7.87 (m, 4 H), 7.73 (t, J = 7.5 Hz, 1 H), 7.54 (t, J = 7.6 Hz, 2 H), 7.46 (d, J = 8.5 Hz, 2 H), 4.73 (s, 2 H). 13C NMR (100 MHz, CDCl3): δ = 186.97, 141.30, 138.67, 134.51, 134.15, 130.89, 129.41, 129.38, 128.66, 63.69. MS (EI): m/z = 294, 296 [M+, M+ + 2]. Anal. Calcd for C14H11ClO3S: C, 57.05; H, 3.76; S, 10.88. Found: C, 57.33; H, 3.89; S, 10.98.