Silver-Catalyzed Efficient Synthesis of Vinylene Carbonate Derivatives from Carbon Dioxide

Rie Ugajin; Satoshi Kikuchi; Tohru Yamada

doi:10.1055/s-0033-1341047

Synlett, Table of Contents

Synlett 2014; 25(08): 1178-1180
DOI: 10.1055/s-0033-1341047

letter

Silver-Catalyzed Efficient Synthesis of Vinylene Carbonate Derivatives from Carbon Dioxide

Authors

Rie Ugajin

Department of Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan Fax: +81(45)5661716 Email: yamada@chem.keio.ac.jp
Satoshi Kikuchi

Department of Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan Fax: +81(45)5661716 Email: yamada@chem.keio.ac.jp
Tohru Yamada*

Department of Chemistry, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan Fax: +81(45)5661716 Email: yamada@chem.keio.ac.jp

Abstract

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Abstract

It was found that the silver salt and base was an efficient catalytic system for the reaction of the secondary propargylic alcohol with carbon dioxide to afford various corresponding vinylene carbonate derivatives in good to high yields under mild conditions.

Key words

alkynes - vinylene carbonates - carbon dioxide - silver - isomerization - Lewis acids

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References

References and Notes

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11 When the reaction was carried out under the balloon pressure, the yield was decreased into 77% yield.
12 General Procedure The reaction was performed using a pressure test tube equipped with a stirring bar in a 50 mL autoclave. To a solution of propargyl alcohol 1 (0.30 mmol) and AgOAc (0.030 mmol, 5.0 mg) in toluene (2.0 mL) was added DBU (0.12 mmol, 18 μL) under an inert gas. Immediately, CO₂ gas was purged, and the reaction mixture was stirred at 30 °C under 1.5 MPa CO₂ pressure. After the reaction was completed, the purification by column chromatography [SiO₂, eluted with n-hexane–EtOAc (100:1)] gave the corresponding carbonate 2.
13 Representative Experimental Data 4-Pentyl-5-phenyl-1,3-dioxol-2-one (2a) Reaction time 24 h; yield 96%; 66.9 mg; colorless oil. ¹H NMR (400 MHz, CDCl₃): δ = 0.91 (t, J = 7.1 Hz, 3 H), 1.37 (m, 4 H), 1.71 (m, 2 H), 2.69 (t, J = 7.6 Hz, 2 H), 7.37–7.48 (m, 5 H). ¹³C NMR (100 MHz, CDCl₃): δ = 13.9, 22.3, 24.8, 26.5, 31.1, 125.2, 125.6, 128.9, 129.0, 137.2, 139.2, 152.4. IR (KBr): 2958, 2932, 2862, 1821, 1449, 1248, 1188, 1098, 1057, 1026, 977, 760, 692. ESI-HRMS: m/z calcd for C₁₄H₁₇O₃ ⁺ [M + H]⁺: 233.1172; found: 233.1177.

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Supplementary Material

Supporting Information (PDF)