Advances in Dearomative Carboxylation of Aromatic Compounds with Carbon Dioxide

doi:10.6023/cjoc202405030

Abstract

Dearomative carboxylation of aromatic compounds with carbon dioxide (CO₂) could be utilized for the synthesis of cyclic carboxylative frameworks. The dearomative carboxylation exhibits advantages such as reconstitution molecular spatial structure, environmental friendliness, mild conditions, high yield, and high selectivity, and is of significant importance in pharmaceutical synthesis and natural product chemistry. The recent advancements in the dearomative carboxylation of aromatics with CO₂ are summarized, including elucidation of the reaction characteristics and the scope of substrates via transition-metal catalysis, photoredox catalysis, and electropromoted chemistry.

Key words: dearomative carboxylation, aromatic compound, carbon dioxide, metal catalysis, photocatalysis, electropromoted chemistry

Cite this article

Jiayuan Li, Yaping Yi, Chanjuan Xi. Advances in Dearomative Carboxylation of Aromatic Compounds with Carbon Dioxide[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3136-3146.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 19

Figure 1. Selected cyclic carboxylic acid derivatives in pharmaceuticals

Figure 2. Aromatic stabilization energies of common aromatic/heteroaromatic rings

Scheme 1. Pd-catalyzed dearomative carboxylation of 3-indole- methanol with CO2

Scheme 2. Pd-catalyzed formation of dicarboxylation products through dearomative carboxylation of 3-indolemethanol with CO2

Scheme 3. Radical trifluoromethylative dearomatization of indoles with CO2

Figure 3. General process of photocatalytic redox cycle

Scheme 4. Visible-light-induced reductive catalytic dearomatization and carboxylation of CO2 via SSET mechanism

Scheme 5. Direct photo-induced dearomatization and bifunctionalization reaction of heteroaromatics

Scheme 6. Reaction of indoles or benzofurans with sodium difluoromethanesulfinate as the radical precursor

Scheme 7. Photocatalyzed α-aminomethyl/dearomative carboxylation of indoles with CO2 and α-aminoalkyl radical precursors

Scheme 8. Dearomatization and carboxylation of inactive aromatics with CO2 constructed via RPCC strategy

Scheme 9. Dearomative carboxylation reaction leading to spirocyclic acid compounds

Scheme 10. Dearomative dicarboxylation of heteroarenes via CO2?-

Scheme 11. Dearomative carboxylation reaction of benzofuran with HCO2Cs

Scheme 12. Dearomative carboxylation of 2-naphthyl-acetoni- trile with HCO2Cs via Birch-type reaction

Scheme 13. Dearomative dicarboxylation reported by Zhu et al.

Scheme 14. Electro-dicarboxylation of CO2 with polycyclic aromatics

Scheme 15. Electrochemical dearomative dicarboxylation of heteroaromatics with CO2

Scheme 16. Electrochemical dearomative carboxylation of electron-deficient naphthalene with CO2

References 59

[1]	Bhutani, P.; Joshi, G.; Raja, N.; Bachhav, N.; Rajanna, P. K.; Bhutani, H.; Paul, A. T.; Kumar, R. J. Med. Chem. 2021, 64, 2339.
[2]	Kang, G.; Strassfeld, D. A.; Sheng, T.; Chen, C.-Y.; Yu, J.-Q. Nature 2023, 618, 519.
[3]	(a) Wertjes, W. C.; Southgate, E. H.; Sarlah, D. Chem. Soc. Rev. 2018, 47, 7996.
	(b) James, M. J.; O'Brien, P.; Taylor, R. J. K.; Unsworth, W. P. Chem. Eur. J. 2016, 22, 2856.
[4]	(a) Zheng, C.; You, S.-L. Nat. Prod. Rep. 2019, 36, 1589. doi: 10.1039/c8np00098k pmid: 30839047
	(b) Liu, Y.-Z.; Song, H.; Zheng, C.; You, S.-L. Nat. Synth. 2022, 1, 203. pmid: 30839047
	(c) Zheng, C.; You, S.-L. ACS Cent. Sci. 2021, 7, 432. pmid: 30839047
[5]	(a) Birch, A. J. Nature 1946, 158, 585.
	(b) Chatterjee, A.; König, B. Angew. Chem., Int. Ed. 2019, 58, 14289.
[6]	(a) Buchner, E.; Curtius, T. Ber. Dtsch. Chem. Ges. 1885, 18, 2371.
	(b) Shi, C.-Y.; Zhu, G.-Y.; Xu, Y.; Teng, M.-Y.; Ye, L.-W. Chin. Chem. Lett. 2023, 34, 108441.
[7]	Reimer, K.; Tiemann, F. Ber. Dtsch. Chem. Ges. 1876, 9, 824.
[8]	Gao, W.; Deng, W.; Gao, Y.; Liang, R.; Jia, Y. Acta Chim. Sinica 2024, 82, 1. (in Chinese)
	(高炜洋, 邓伟超, 高扬, 梁仁校, 贾义霞, 化学学报, 2024, 82, 1.)
[9]	Harman, W. D.; Taube, H. J. Am. Chem. Soc. 1988, 110, 7906.
[10]	Ohno, H.; Maeda, S.; Okumura, M.; Wakayama, R.; Tanaka, T. Chem. Commun. 2002, 316.
[11]	López Ortiz, F.; Iglesias, M. J.; Fernández, I.; Andújar Sánchez, C. M.; Ruiz Gómez, G. Chem. Rev. 2007, 107, 1580.
[12]	Bariwal, J.; Voskressensky, L. G.; Van der Eycken, E. V. Chem. Soc. Rev. 2018, 47, 3831.
[13]	(a) Correa, A.; Martin, R. Angew. Chem., Int. Ed. 2009, 48, 6201.
	(b) Gui, Y.-Y.; Zhou, W.-J.; Ye, J.-H.; Yu, D.-G. ChemSusChem 2017, 10, 1337.
	(c) James, M. J.; Schwarz, J. L.; Strieth-Kalthoff, F.; Wibbeling, B.; Glorius, F. J. Am. Chem. Soc. 2018, 140, 8624.
	(d) Zhu, M.; Zheng, C.; Zhang, X.; You, S.-L. J. Am. Chem. Soc. 2019, 141, 2636.
[14]	Wang, L.; Qi, C.; Xiong, W; Jiang, H. Chin. J. Catal. 2022, 43, 1598. doi: 10.1016/S1872-2067(21)64029-9
[15]	Ran, C.-K.; Xiao, H.-Z.; Liao, L.-L.; Ju, T.; Zhang, W.; Yu, D.-G. Natl. Sci. Open. 2023, 2, 20220024.
[16]	Ran, C.-K.; Chen, X.-W.; Gui, Y.-Y.; Liu, J.; Song, L.; Ren, K.; Yu, D.-G. Sci. China Chem. 2020, 63, 1336.
[17]	(a) Roche, S. P.; Porco Jr., J. A. Angew. Chem., nt. Ed. 2011, 50, 4068.
	(b) Bringezu, S. J. Ind. Ecol. 2014, 18, 327.
	(c) Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nat. Commun. 2015, 6, 5933.
	(d) Klankermayer, J.; Wesselbaum, S.; Beydoun, K.; Leitner, W. Angew. Chem., Int. Ed. 2016, 55, 7296.
	(e) Artz, J.; Müller, T. E.; Thenert, K. Kleinekorte, J.; Meys, R.; Sternberg, A.; Bardow, A.; Leitner, W. Chem. Rev. 2018, 118, 434.
[18]	Ran, C.-K.; Liao, L.-L.; Gao, T.-Y.; Gui, Y.-Y.; Yu, D.-G. Curr. Opin. Green Sustainable Chem. 2021, 32, 100525.
[19]	Wang, S.; Du, G.; Xi, C. Org. Biomol. Chem. 2016, 14, 3666.
[20]	Fan, Z.; Zhang, Z.; Xi, C. ChemSusChem 2020, 13, 6201.
[21]	Senboku, H.; Katayama, A. Curr. Opin. Green Sustainable Chem. 2017, 3, 50.
[22]	Juliá-Hernández, F.; Moragas, T.; Cornella, J.; Martin, R. Nature 2017, 545, 84.
[23]	Hong, J.; Li, M.; Zhang, J.; Sun, B; Mo, F. ChemSusChem 2019, 12, 6.
[24]	Bertuzzi, G.; Cerveri, A.; Lombardi, L.; Bandini, M. Chin. J. Chem. 2021, 39, 3116.
[25]	Buttard, F.; Guinchard, X. ACS Catal. 2023, 13, 9442.
[26]	Mita, T.; Ishii, S.; Higuchi, Y.; Sato, Y. Org. Lett. 2018, 20, 7603.
[27]	Ye, J.-H.; Zhu, L.; Yan, S.-S; Miao, M.; Zhang, X.-C.; Zhou, W.-J.; Li, J.; Lan, Y.; Yu, D.-G. ACS Catal. 2017, 7, 8324.
[28]	(a) McCusker, J. K. Science 2001, 293, 1599. pmid: 11533464
	(b) Zheng, Y.; Pan, Z.-M.; Wang, X.-C. Chin. J. Catal. 2013, 34, 524. pmid: 11533464
	(c) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176. pmid: 11533464
[29]	Okumura, M.; Sarlah, D. Eur. J. Org. Chem. 2020, 1259.
[30]	Gong, E.; Ali, S.; Hiragond, C. B.; Kim, H. S.; Powar, N. S.; Kim, D.; Kim, H.; In, S. Energy Environ. Sci. 2022, 15, 880.
[31]	Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[32]	Zhu, M.; Zhang, X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2022, 55, 2510.
[33]	Yatham, V. R.; Shen, Y.; Martin, R. Angew. Chem., Int. Ed. 2017, 56, 10915.
[34]	Hou, J.; Ee, A.; Cao, H.; Ong, H.-W.; Xu, J.-H.; Wu, J. Angew. Chem. Int. Ed. 2018, 57, 17220.
[35]	Fu, Q.; Bo, Z.-Y.; Ye, J.-H.; Ju, T.; Huang, H.; Liao, L.-L.; Yu, D.-G. Nat. Commun. 2019, 10, 3592.
[36]	Wang, H.; Gao, Y.; Zhou, C.; Li, G. J. Am. Chem. Soc. 2020, 142, 8122. doi: 10.1021/jacs.0c03144 pmid: 32309942
[37]	Zhou, W.-J.; Wang, Z.-H.; Liao, L.-L.; Jiang, Y.-X.; Cao, K.-G.; Ju, T.; Li, Y.; Cao, G.-M.; Yu, D.-G. Nat. Commun. 2020, 11, 3263.
[38]	Yi, Y.; Fan, Z.; Xi, C. Green Chem. 2022, 24, 7894.
[39]	Gao, W.; Yang, Q.; Yang, H.; Yao, Y.; Bai, J.; Sun, J.; Sun, S. Org. Lett. 2024, 26, 467.
[40]	Gao, Y.; Wang, H.; Chi, Z.; Yang, L.; Zhou, C.; Li, G. CCS Chem. 2022, 4, 1565.
[41]	Yi, Y.; Xi, C. Chin. J. Catal. 2022, 43, 1652.
[42]	Otero, M. D.; Batanero, B.; Barba, F. Tetrahedron Lett. 2006, 47, 2171.
[43]	Gui, Y.-Y.; Yan, S.-S.; Wang, W.; Chen, L.; Zhang, W.; Ye, J.-H.; Yu, D.-G. Sci. Bull. 2023, 68, 3124.
[44]	Tan, G.; Das, M.; Keum, H.; Bellotti, P.; Daniliuc, C.; Glorius, F. Nat. Chem. 2022, 14, 1174.
[45]	Yang, Z.; Yu, Y.; Lai, L.; Zhou, L.; Ye, K.; Chen, F.-E. Green Synth. Catal. 2021, 2, 19.
[46]	Cao, Y.; He, X.; Wang, N.; Li, H.-R.; He, L.-N. Chin. J. Chem. 2018, 36, 644.
[47]	Huang, H.; Ye, J.-H.; Zhu, L.; Ran, C.-K.; Miao, M.; Wang, W.; Chen, H.; Zhou, W.-J.; Lan, Y.; Yu, B.; Yu, D.-G. CCS Chem. 2020, 3, 1746.
[48]	Ye, J.-H.; Ju, T.; Huang, H.; Liao, L.-L.; Yu, D.-G. Acc. Chem. Res. 2021, 54, 2518.
[49]	Hang, W.; Li, D.; Zou, S.; Xi, C. J. Org. Chem. 2022, 88, 5007. doi: 10.1021/acs.joc.2c01840 pmid: 36126282
[50]	Liu, C.; Shen, N.; Shang, R. Nat. Commun. 2022, 13, 354.
[51]	Liu, C.; Li, K.; Shang, R. ACS Catal. 2022, 12, 4103.
[52]	Chmiel, A. F.; Williams, O. P.; Chernowsky, C. P.; Yeung, C. S.; Wickens, Z. K. J. Am. Chem. Soc. 2021, 143, 10882. doi: 10.1021/jacs.1c05988 pmid: 34255971
[53]	Ju, T.; Zhou, Y.-Q.; Cao, K.-G.; Fu, Q.; Ye, J.-H.; Sun, G.-Q.; Liu, X.-F.; Chen, L.; Liao, L.-L.; Yu, D.-G. Nat. Catal. 2021, 4, 304.
[54]	Mangaonkar, S. R.; Hayashi, H.; Takano, H.; Kanna, W.; Maeda, S.; Mita, T. ACS Catal. 2023, 13, 2482.
[55]	Xu, P.; Wang, S.; Xu, H.; Liu, Y.-Q.; Li, R.-B.; Liu, W.-W.; Wang, X.-Y.; Zou, M.-L.; Zhou, Y.; Guo, D.; Zhu, X. ACS Catal. 2023, 13, 2149.
[56]	Yuan, G.; Li, L.; Jiang, H.; Qi, C.; Xie, F. Chin. J. Chem. 2010, 28, 1983.
[57]	You, Y.; Kanna, W.; Takano, H.; Hayashi, H.; Maeda, S.; Mita, T. J. Am. Chem. Soc. 2022, 144, 3685.
[58]	(a) Li, C.; Yuan, G.; Jiang, H. Chin. J. Chem. 2010, 28, 1685.
	(b) Li, C.-H.; Yuan, G.-Q.; Ji, X.-C.; Wang, X.-J.; Ye, J.-S.; Jiang, H.-F. Electrochim. Acta. 2011, 56, 1529.
	(c) Matthessen, R.; Fransaer, J.; Binnemans, K.; Vos, D. E. D. RSC Adv. 2013, 3, 4634.
	(d) Gui, Y.-Y.; Chen, X.-W.; Mo, X.-Y.; Yue, J.-P.; Yuan, R.; Liu, Y.; Liao, L.-L.; Ye, J.-H.; Yu, D.-G. J. Am. Chem. Soc. 2024, 146, 2919.
[59]	Rawat, V. K.; Hayashi, H.; Katsuyama, H.; Mangaonkar, S. R.; Mita, T. Org. Lett. 2023, 25, 4231.

二氧化碳参与的芳香化合物去芳构化羧化反应研究进展