Synlett 2013; 24(14): 1848-1850
DOI: 10.1055/s-0033-1339309
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Carbonylative Cyclization of β-Bromo-α,β-unsaturated Carboxylic Acids Leading to Maleic Anhydrides

Yeon Kyu Bae
Department of Applied Chemistry, Kyungpook National University, Daegu 702-701, Republic of Korea   Fax: +82(53)9506594   eMail: cscho@knu.ac.kr
,
Chan Sik Cho*
Department of Applied Chemistry, Kyungpook National University, Daegu 702-701, Republic of Korea   Fax: +82(53)9506594   eMail: cscho@knu.ac.kr
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Publikationsverlauf

Received: 13. Mai 2013

Accepted after revision: 02. Juni 2013

Publikationsdatum:
01. August 2013 (online)


Abstract

β-Bromo-α,β-unsaturated carboxylic acids are carbonylatively cyclized under carbon monoxide pressure in acetic acid in the presence of a catalytic amount of a palladium catalyst along with a base to give the corresponding maleic anhydrides in high yields.

 
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  • 13 Yields of Several β-Bromo-α,β-unsaturated Carboxylic Acids from the Corresponding β-Bromo-α,β-unsaturated Aldehydes and Spectroscopic DataCompound 1c: 250 mg (89%); solid; mp 136–137 °C. 1H NMR (400 MHz, CDCl3): δ = 1.89–2.02 (m, 2 H), 2.45–2.54 (m, 1 H), 2.76–2.83 (m, 3 H), 2.87–2.95 (m, 1 H), 7.20–7.25 (m, 3 H), 7.30–7.34 (m, 2 H). 13C NMR (100 MHz, CDCl3): δ = 30.98, 36.37, 38.71, 39.04, 126.88, 126.95, 128.85, 129.22, 129.75, 144.59, 171.93.Compound 1f: 246 mg (85%); solid; mp 116–117 °C. 1H NMR (400 MHz, CDCl3): δ = 1.33–1.38 (m, 12 H), 1.55–1.61 (m, 2 H), 1.72–1.78 (m, 2 H), 2.44–2.48 (m, 2 H), 2.58–2.62 (m, 2 H). 13C NMR (100 MHz, CDCl3): δ = 22.47, 22.82, 24.34, 24.39, 24.44, 24.58, 25.72, 25.98, 28.66, 33.91, 128.44, 134.84, 173.57.Compound 1g: 127 mg (50%); solid; mp 123–124 °C. 1H NMR (400 MHz, CDCl3): δ = 2.72–2.76 (m, 2 H), 2.86–2.90 (m, 2 H), 7.15–7.17 (m, 1 H), 7.27–7.34 (m, 2 H), 7.85–7.89 (m, 1 H). 13C NMR (100 MHz, CDCl3): δ = 27.51, 27.79, 127.27, 127.39, 128.68, 129.52, 129.58, 130.34, 133.53, 137.56, 172.32.Compound 1h: 159 mg (63%); solid; mp 133–134 °C. 1H NMR (400 MHz, CDCl3): δ = 2.87–2.91 (m, 2 H), 2.96–3.00 (m, 2 H), 7.14–7.17 (m, 1 H), 7.22–7.25 (m, 3 H). 13C NMR (100 MHz, CDCl3): δ = 28.99, 34.70, 124.43, 124.63, 127.29, 128.09, 128.59, 130.76, 133.01, 133.39, 172.51.
  • 14 General Procedure for the Palladium-Catalyzed Carbonylative Cyclization of β-Bromo-α,β-unsaturated Carboxylic Acids Leading to Maleic AnhydridesTo a 50 mL stainless steel autoclave were added β-bromo-α,β-unsaturated carboxylic acid 1 (0.5 mmol), PdCl2 (0.025 mmol), dppp (0.03 mmol), Et3N (2 mmol), and AcOH (8 mL). After the system was flushed and then pressurized with CO to 10 atm, the reaction mixture was allowed to react at 120 °C for 3 h. The reaction mixture was poured into H2O and extracted with EtOAc twice. The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude mixture was purified by column chromatography (silica gel, hexane–EtOAc mixture) to afford maleic anhydrides 2. Except for 2f, all products are known.Compound 2f: 117 mg (99%); white solid; mp 87–88 °C. 1H NMR (400 MHz, CDCl3): δ = 1.27–1.34 (m, 4 H), 1.38–1.44 (m, 8 H), 1.75–1.81 (m, 4 H), 2.50 (t, J = 7.1 Hz, 4 H). 13C NMR (100 MHz, CDCl3): δ = 22.09, 22.23, 24.34, 25.14, 25.48, 145.10, 166.05. Anal. Calcd (%) for C14H20O3: C, 71.16; H, 8.53. Found: C, 71.11; H, 8.67.