Visible-Light-Mediated Oxidative Decarboxylative Coupling of Cinnamic Acid Derivatives with Tetrahydrofuran

Abstract

A visible-light-mediated protocol for direct oxidative decarboxylative coupling of various cinnamic acid derivatives with tetrahydrofuran was developed, leading to simple preparations of a range of vinyltetrahydrofurans under operationally mild and convenient conditions.

Key words

alkenes - coupling - oxidations - carboxylic acids - photochemistry - radical reactions - decarboxylations

• References

• 1a Gooßen LJ, Rodríguez N, Gooßen K. Angew. Chem. Int. Ed. 2008; 47: 3100
• 1b Rodríguez N, Gooßen LJ. Chem. Soc. Rev. 2011; 40: 5030
• 1c Park K, Lee S. RSC Adv. 2013; 3: 14165
• 1d Dzik WI, Lange PP, Gooßen LJ. Chem. Sci. 2012; 3: 2671
• 2a Meerwein H, Bückner E, van Emster K. J. Prakt. Chem. 1939; 152: 237
• 2b Brunner WH, Kustatscher J. Monatsh. Chem. 1951; 82: 100
• 2c Rondestvedt CS. Jr. Org. React. (N. Y.) 1976; 24: 225
• 3a Zhao J, Zhou W, Han J, Li G, Pan Y. Tetrahedron Lett. 2013; 54: 6507
• 3b Zhang F, Greaney MF. Angew. Chem. Int. Ed. 2010; 49: 2768
• 3c Wang Z, Ding Q, He X, Wu J. Org. Biomol. Chem. 2009; 7: 863
• 3d Kim H, Lee PH. Adv. Synth. Catal. 2009; 351: 2827
• 3e Bhunia S, Ghorpade S, Huple DB, Liu R.-S. Angew. Chem. Int. Ed. 2012; 51: 2939
• 3f Bloom S, Pitts CR, Woltornist R, Griswold A, Holl MG, Lectka T. Org. Lett. 2013; 15: 1722
• 3g Liu X, Sun B, Xie Z, Qin X, Liu L, Lou H. J. Org. Chem. 2013; 78: 3104
• 4 Singh R, Allam BK, Singh N, Kumari K, Singh SK, Singh KN. Org. Lett. 2015; 17: 2656
• 5a Noble A, McCarver SJ, MacMillan DW. C. J. Am. Chem. Soc. 2015; 137: 624
• 5b Ventre S, Petronijevic FR, MacMillan DW. C. J. Am. Chem. Soc. 2015; 137: 5654
• 5c Chu L, Lipshultz JM, MacMillan DW. C. Angew. Chem. Int. Ed. 2015; 54: 7929
• 5d Zuo Z, MacMillan DW. C. J. Am. Chem. Soc. 2014; 136: 5257
• 5e Chu L, Ohta C, Zuo Z, MacMillan DW. C. J. Am. Chem. Soc. 2014; 136: 10886
• 6 Xie J, Xu P, Li H, Xue Q, Jin H, Cheng Y, Zhu C. Chem. Commun. 2013; 49: 5672
• 7a Rye CE, Barker D. Synlett 2009; 3315
• 7b Miles SM, Marsden SP, Leatherbarrow RJ, Coates WJ. J. Org. Chem. 2004; 69: 6874
• 7c Mammoli V, Bonifazi A, Del Bello F, Diamanti E, Giannella M, Hudson AL, Mattioli L, Perfumi M, Piergentili A, Quaglia W, Titomanlio F, Pigini M. Bioorg. Med. Chem. 2012; 20: 2259
• 7d Liu D, Liu C, Li H, Lei A. Angew. Chem. Int. Ed. 2013; 52: 4453
• 7e Vilotijevic I, Jamison TF. Angew. Chem. Int. Ed. 2009; 48: 5250
• 7f Wolfe JP, Hay MB. Tetrahedron 2007; 63: 261
• 8 Wan M, Meng Z, Lou H, Liu L. Angew. Chem. Int. Ed. 2014; 53: 13845
• 9 Li J, Zhang J, Tan H, Wang DZ. Org. Lett. 2015; 17: 2522
• 10a Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785
• 10b Yoon TP, Ischay MA, Du JN. Nat. Chem. 2010; 2: 527
• 10c Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617
• 10d Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
• 10e Xie J, Jin H, Xu P, Zhu C. Tetrahedron Lett. 2014; 55: 36
• 10f Schultz DM, Yoon TP. Science 2014; 343: 1239176
• 11 2-Arylvinyl Ethers 3; General Procedure Ru(bpy)₃Cl₂·6H₂O (2 mol%, 6 mg), cinnamic acid derivative 1 (1 equiv, 0.5 mmol), benzoyl peroxide (2.8 equiv, 1.4 mmol), anhyd ether 2 (3 mL), and anhyd MeCN (3 mL) were added to a 10 mL reaction vessel equipped with a magnetic stirrer bar. The mixture was irradiated with a 46 W CFL at r.t. for 4–6 h. The yield was determined by isolation of the product using flash chromatography. 2-[(E)-2-Phenylvinyl]tetrahydrofuran (3a) Colorless oil; yield: 63.4 mg (73%). ¹H NMR (400 MHz, CDCl₃): δ = 7.38 (d, J = 7.3 Hz, 2 H), 7.34–7.27 (m, 2 H), 7.25–7.17 (m, 1 H), 6.59 (d, J = 15.9 Hz, 1 H), 6.21 (dd, J = 15.9, 6.6 Hz, 1 H), 4.48 (dd, J = 6.9 Hz, 1 H), 3.98 (dd, J = 14.5, 7.4 Hz, 1 H), 3.85 (dd, J = 14.2, 7.8 Hz, 1 H), 2.13 (ddd, J = 14.5, 9.6, 6.1 Hz, 1 H), 2.07–1.87 (m, 2 H), 1.79–1.68 (m, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 136.83, 130.49, 130.41, 128.47, 127.45, 126.42, 79.63, 68.14, 32.36, 25.88. HRMS: m/z [M + H]⁺ calcd for C₁₂H₁₅O: 175.1117; found: 175.1120. 2-[(E)-2-(4-Fluorophenyl)vinyl]tetrahydrofuran (3c) Colorless oil; yield: 57.6 mg (60%). ¹H NMR (400 MHz, CDCl₃): δ = 7.40–7.29 (m, 2 H), 6.99 (t, J = 8.7 Hz, 2 H), 6.54 (d, J = 15.8 Hz, 1 H), 6.12 (dd, J = 15.8, 6.6 Hz, 1 H), 4.45 (dd, J = 13.4, 6.7 Hz, 1 H), 3.97 (dd, J = 14.5, 7.4 Hz, 1 H), 3.84 (dd, J = 14.2, 7.8 Hz, 1 H), 2.17–2.07 (m, 1 H), 2.04–1.91 (m, 2 H), 1.70 (ddd, J = 15.8, 12.0, 7.5 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 132.99, 130.24, 129.31, 127.93, 115.49, 115.28, 79.57, 68.17, 32.37, 25.91. HRMS: m/z [M + H]⁺ calcd for C₁₂H₁₄FO: 193.1023; found: 193.1024. 2-[(E)-2-(5-Bromo-2-fluorophenyl)vinyl]tetrahydrofuran (3l) Colorless oil; yield: 58.4 mg (43%). ¹H NMR (400 MHz, CDCl₃): δ = 7.48 (dd, J = 8.8, 5.4 Hz, 1 H), 7.22 (dd, J = 9.8, 3.0 Hz, 1 H), 6.87 (d, J = 15.7 Hz, 1 H), 6.85–6.79 (m, 1 H), 6.16 (dd, J = 15.7, 6.4 Hz, 1 H), 4.53 (dd, J = 12.8, 6.4 Hz, 1 H), 3.99 (dd, J = 14.6, 7.3 Hz, 1 H), 3.86 (dd, J = 14.2, 7.8 Hz, 1 H), 2.19–2.10 (m, 1 H), 2.05–1.92 (m, 2 H), 1.73 (ddd, J = 15.5, 12.1, 7.3 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 160.79, 138.54 (d, J = 7.7 Hz), 134.88, 134.03 (d, J = 8.2 Hz), 128.32, 117.69 (d, J = 3.0 Hz), 115.94 (d, J = 22.7 Hz), 113.74 (d, J = 23.3 Hz), 79.12, 68.32, 32.29, 25.82. HRMS: m/z [M + H]⁺ calcd for C₁₂H₁₃BrFO: 271.0128; found: 271.0131.
• 12 Campagna S, Puntoriero F, Nastasi F, Bergamini G, Balzani V. Top. Curr. Chem. 2007; 280: 117
• 13 Johnson WS, Hein WE. J. Am. Chem. Soc. 1949; 71: 2913