Dess–Martin Periodinane/Brønsted Acid-Mediated Tandem Oxidation/Cyclization of Homopropargylic Alcohols for Synthesis of Trisubstituted Furans

Abstract

A facile, efficient, and metal-free single-flask procedure for the synthesis of trisubstituted furans from simple readily available homopropargylic alcohols is described. A combination of Dess–Martin periodinane, H₂O, and TsOH·H₂O plays a crucial role in the formation of the trisubstituted furans. The advantages of this method include operational ease, mild reaction conditions, and good functional-group tolerance.

Key words

furans - Dess–Martin oxidation - 5-endo-dig cyclization - Brønsted acids - homopropargylic alcohols

Publikationsverlauf

Eingereicht: 16. Februar 2023

Angenommen nach Revision: 06. März 2023

Accepted Manuscript online:
06. März 2023

Artikel online veröffentlicht:
20. März 2023

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• 23 5-Ethyl-3-(2-methoxyphenyl)-2-phenylfuran (2b); Typical Procedure Homopropargylic alcohol 1b (0.3 mmol) and TsOH·H₂O (5 mol%) were dissolved in anhyd CH₂Cl₂ (3 mL) under argon in a 10 mL vial equipped with a magnetic stirrer bar and a septum. Distilled H₂O (0.9 mmol) and Dess–Martin periodinane (0.6 mmol) were successively added to the stirred solution at ambient temperature. The septum was replaced with a screw cap under argon, and the resulting mixture (0.1 M) was stirred in an oil bath at 30 °C for 60 h until the reaction was complete (TLC). The reaction was quenched with sat. aq NaHCO₃ (1 mL) and Na₂S₂O₃ (1 mL), and the resulting mixture was stirred for 30 min. The separated aqueous layer was extracted with CHCl₃, and the combined organic layers were washed with brine, dried (MgSO₄), and concentrated in vacuo. The resulting crude residue was purified by flash chromatography (silica gel) to give a colorless oil; yield: 60.1 mg (72%), R_f = 0.59 (EtOAc–hexane, 3:7). ¹H NMR (400 MHz, CDCl₃): δ = 7.51 (dd, J = 1.2, 8.4 Hz, 2 H), 7.41–7.28 (m, 4 H), 7.22 (tt, J = 1.2, 7.6 Hz, 1 H), 7.03 (d, J = 7.2 Hz, 2 H), 6.20 (t, J = 1.2 Hz, 1 H), 3.77 (s, 3 H), 2.83 (dq, J = 1.2, 7.2 Hz, 2 H), 1.39 (t, J = 7.2 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 156.7, 156.5, 147.4, 132.1, 131.5, 128.8, 128.2, 126.7, 125.3, 123.9, 120.8, 119.0, 111.3, 109.6, 55.5, 21.6, 12.2. HRMS (ESI-TOF): m/z [M + H]⁺ calcd for C₁₉H₁₉O₂: 279.1385; found: 279.1391.

For selected examples of oxidative ring-opening reaction of furans see:
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