Organic Base-Mediated Carboxylation of (Hetero)aromatic Compounds Using Supercritical Carbon Dioxide (scCO₂)

Abstract

A straightforward site-selective method for the direct carboxylation of resorcinols (3-hydroxyphenol derivatives), phenols, and indoles is reported. The products were obtained in moderate to high yields using supercritical carbon dioxide as an electrophile and solvent under basic conditions. This method offers solvent and metal free conditions without the cumbersome exclusion of air or water with convenient purification.

Key words

supercritical carbon dioxide - Kolbe–Schmitt - C–H carboxylation - metal free - solvent free

Publication History

Received: 26 May 2022

Accepted after revision: 08 July 2022

Accepted Manuscript online:
08 July 2022

Article published online:
16 August 2022

• References

• 1a Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
• 1b Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
• 2 Luo J, Larrosa I. ChemSusChem 2017; 10: 3317
• 3a Storace L, Anzalone L, Confalone PN, Davis WP, Fortunak JM, Giangiordano M, Haley JJ, Kamholz K, Li H.-Y, Ma P. Org. Process Res. Dev. 2002; 6: 54
• 3b Ratni H, Rogers-Evans M, Bissantz C, Grundschober C, Moreau J.-L, Schuler F, Fischer H, Alvarez Sanchez R, Schnider P. J. Med. Chem. 2015; 58: 2275
• 3c Park SY, Oh YJ, Lho Y, Jeong JH, Liu K.-H, Song J, Kim S.-H, Ha E, Seo YH. Eur. J. Med. Chem. 2018; 143: 390
• 3d Woodhead AJ, Angove H, Carr MG, Chessari G, Congreve M, Coyle JE, Cosme J, Graham B, Day PJ, Downham R. J. Med. Chem. 2010; 53: 5956
• 4a Friis SD, Andersen TL, Skrydstrup T. Org. Lett. 2013; 15: 1378
• 4b Zhang M, Xie J, Zhu C. Nat. Commun. 2018; 9: 1
• 5 Juliá-Hernández F, Moragas T, Cornella J, Martin R. Nature 2017; 545: 84
• 6a Laserna V, Martin E, Escudero-Adán EC, Kleij AW. Adv. Synth. Catal. 2016; 358: 3832
• 6b Tominaga K.-i, Sasaki Y. J. Mol. Catal. A: Chem. 2004; 220: 159
• 6c Aresta M, Tommasi I. Energy Convers. Manag. 1997; 38: S373
• 7 Tominaga K.-i. Catal. Today 2006; 115: 70
• 8 Lindsey AS, Jeskey H. Chem. Rev. 1957; 57: 583
• 9 Stark A, Huebschmann S, Sellin M, Kralisch D, Trotzki R, Ondruschka B. Chem. Eng. Technol. 2009; 32: 1730
• 10 Kolbe H. J. Prakt. Chem. 1874; 10: 89
• 11 Schmitt R. J. Prakt. Chem. 1885; 31: 397
• 12 Marasse S. German Patent 73259, 1893
• 13 Krtschil U, Hessel V, Reinhard D, Stark A. Chem. Eng. Technol. 2009; 32: 1774
• 14 Baine O, Adamson GF, Barton JW, Fitch JL, Swayampati DR, Jeskey H. J. Org. Chem. 1954; 19: 510
• 15a Luo J, Preciado S, Xie P, Larrosa I. Chem. Eur. J. 2016; 22: 6798
• 15b Yoo W.-J, Capdevila MG, Du X, Kobayashi S. Org. Lett. 2012; 14: 5326
• 15c Nemoto K, Onozawa S, Egusa N, Morohashi N, Hattori T. Tetrahedron Lett. 2009; 50: 4512
• 15d Nemoto K, Tanaka S, Konno M, Onozawa S, Chiba M, Tanaka Y, Sasaki Y, Okubo R, Hattori T. Tetrahedron 2016; 72: 734
• 16a Rayner CM, Rose PM, Barnes DC. Synthetic Organic Chemistry in Supercrtical Fluids . In Handbook of Green Chemistry, Vol. 4. Anastas PT, Crabtree RH. Wiley-VCH; Weinheim: 2010: 189-241
• 16b Knez Ž, Pantić M, Cör D, Novak Z, Hrnčič MK. Chem. Eng. Process 2019; 141: 107532
• 16c Amandi R, Hyde JR, Ross SK, Lotz TJ, Poliakoff M. Green Chem. 2005; 7: 288
• 17a Pena-Pereira F, Kloskowski A, Namieśnik J. Green Chem. 2015; 17: 3687
• 17b Sheldon RA. Curr. Opin. Green Sustain. Chem. 2019; 18: 13
• 18a Gupta P, Mahajan A. RSC Adv. 2015; 5: 26686
• 18b Suresh P, Basu PK. J. Pharm. Innov. 2008; 3: 175
• 19 Constable DJ, Dunn PJ, Hayler JD, Humphrey GR, Leazer JL. Jr, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells A. Green Chem. 2007; 9: 411
• 20 Shanthi B, Palanivelu K. Ultrason. Sonochem. 2015; 27: 268
• 21 Plasch K, Hofer G, Keller W, Hay S, Heyes DJ, Dennig A, Glueck SM, Faber K. Green Chem. 2018; 20: 1754
• 22 Sadamitsu Y, Okumura A, Saito K, Yamada T. Chem. Commun. 2019; 55: 9837
• 23 Iijima T, Yamaguchi T. Tetrahedron Lett. 2007; 48: 5309
• 24a Iijima T, Yamaguchi T. Appl. Catal., A. 2008; 345: 12
• 24b Iijima T, Yamaguchi T. J. Mol. Catal. A: Chem. 2008; 295: 52
• 25a Qu R.-Y, Liu Y.-C, Wu Q.-Y, Chen Q, Yang G.-F. Tetrahedron 2015; 71: 8123
• 25b Blaisdell TP, Morken JP. J. Am. Chem. Soc. 2015; 137: 8712
• 26 Hale DK, Hawdon AR, Jones JI, Packham DI. J. Chem. Soc. 1952; 3503
• 27 Calvo-Castañera F, Álvarez-Rodríguez J, Candela N, Maroto-Valiente Á. Nanomaterials 2021; 11: 190
• 28a Lin H, Doebelin C, Patouret R, Garcia-Ordonez RD, Chang MR, Dharmarajan V, Bayona CR, Cameron MD, Griffin PR, Kamenecka TM. Bioorg. Med. Chem. Lett. 2018; 28: 1313
• 28b Congreve MS, Callaghan O, Chessari G, Cowan SR, Frederickson M, Murray CW, Vinkovic M. Patent WO2007072041, 2007
• 28c Nishi T, Hasegawa M, Nakamoto Y, Ochiai Y, Kitazawa R, Susaki H. Patent WO2011024933, 2011
• 29 Yoo W.-J, Nguyen TV, Capdevila MG. J. Heterocycl. Chem. 2015; 90: 1196
• 30 Dunetz JR, Magano J, Weisenburger GA. Org. Process Res. Dev. 2016; 20: 140
• 31 Shen G, Blagg BS. J. Org. Lett. 2005; 7: 2157
• 32 Castro-Godoy WD, Schmidt LC, Argüello JE. Eur. J. Org. Chem. 2019; 3035
• 33 Wu Y.-Q, Lu H.-J, Zhao W.-T, Zhao H.-Y, Lin Z.-Y, Zhang D.-F, Huang H.-H. Synth. Commun. 2020; 50: 813
• 34 Lang M, Mühlbauer A, Gräf C, Beyer J, Lang-Fugmann S, Polborn K, Steglich W. Eur. J. Org. Chem. 2008; 816
• 35 Komiyama M, Sugigura I, Hirai H. J. Mol. Catal. 1986; 36: 271
• 36 Fujiwara AN, Acton EM. Can. J. Chem. 1970; 48: 1346
• 37 Sreenivasulu R, Tej MB, Jadav SS, Sujitha P, Kumar CG, Raju RR. J. Mol. Struct. 2020; 1208: 127875
• 38 Martin JS, Mackenzie CJ, Gilbert IH. J. Org. Chem. 2021; 86: 11333
• 39 Velavan A, Sumathi S, Balasubramanian K. Eur. J. Org. Chem. 2013; 3148