European Journal of Chemistry

Benzoin condensation of aromatic aldehydes catalyzed by N-heterocyclic carbenes under mild conditions

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Published: Mar 31, 2019
DOI: https://doi.org/10.5155/eurjchem.10.1.1-6.1826
Keywords:
Aldehydes, Heterocycles, Organocatalysis, Room temperature, Benzoin condensation, N-heterocyclic carbenes
Section
Research Article
Issue
Vol. 10 No. 1 (2019): March 2019
Dates
Received 2018-12-13
Accepted 2019-01-01
Published 2019-03-31
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Isabel Monreal-Leyva
Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA
http://orcid.org/0000-0002-7270-7502
Breanna Rose Attema
Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA
http://orcid.org/0000-0002-5231-9430
Nuri Bae
Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA
Haishi Cao
Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA
http://orcid.org/0000-0002-6789-0998
Hector Palencia
Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849, USA
http://orcid.org/0000-0001-8634-8232

Abstract

The benzoin condensation was used to evaluate the catalytic activity of different N-heterocyclic carbenes as a function of their structure and N-substituents. There is a correlation between the length of an N-alkyl substituent and its performance as an organocatalyst. Heteroaromatic aldehydes were found to be the most reactive, among the screened substrates, finishing the reaction in 30 minutes, with almost quantitative yields. On the other hand, p-nitrobenzaldehyde, a strongly electrophilic aldehyde, was the least reactive. Electronic effects have little influence on the reaction yield but steric effects can dramatically reduce it. The preformed organocatalyst reacts faster than the generated in situ, with minimum solvent.


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Monreal-Leyva, I.; Attema, B. R.; Bae, N.; Cao, H.; Palencia, H. Benzoin Condensation of Aromatic Aldehydes Catalyzed by N-Heterocyclic Carbenes under Mild Conditions. Eur. J. Chem. 2019, 10, 1-6.

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References

[1]. Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T. Chem. Rev. 2015, 115, 9307-9387.
https://doi.org/10.1021/acs.chemrev.5b00060

[2]. Feroci, M.; Chiarotto, I.; Orsini, M.; Pelagalli, R.; Inesi, A. Chem. Commun. 2012, 48, 5361-5363.
https://doi.org/10.1039/c2cc30371j

[3]. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511-3522.
https://doi.org/10.1039/c2cs15333e

[4]. Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem. Int. Ed. 2007, 46, 2988-3000.
https://doi.org/10.1002/anie.200603380

[5]. Fu, Z.; Xu, J.; Zhu, T.; Leong, W. W. Y.; Chi, Y. R. Nat. Chem. 2013, 5, 835-839.
https://doi.org/10.1038/nchem.1710

[6]. Biju, A. T.; Kuhl, N.; Glorius, F. Accounts Chem. Res. 2011, 44, 1182-1195.
https://doi.org/10.1021/ar2000716

[7]. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606-5655.
https://doi.org/10.1021/cr068372z

[8]. Yetra, S. R.; Bhunia, A.; Patra, A.; Mane, M. V.; Vanka, K.; Biju, A. T. Adv. Synth. Catal. 2013, 355, 1089-1097.
https://doi.org/10.1002/adsc.201300219

[9]. Chauhan, P.; Enders, D. Angew. Chem. Int. Ed. 2014, 53, 1485-1487.
https://doi.org/10.1002/anie.201309952

[10]. Dell'Amico, L.; Rassu, G.; Zambrano, V.; Sartori, A.; Curti, C.; Battistini, L.; Pelosi, G.; Casiraghi, G.; Zanardi, F. J. Am. Chem. Soc. 2014, 136, 11107-11114.
https://doi.org/10.1021/ja5054576

[11]. Zhu, T.; Mou, C.; Li, B.; Smetankova, M.; Song, B. -A.; Chi, Y. R. J. Am. Chem. Soc. 2015, 137, 5658-5661.
https://doi.org/10.1021/jacs.5b02219

[12]. Herzberger, J.; Niederer, K.; Pohlit, H.; Seiwert, J.; Worm, M.; Wurm, F. R.; Frey, H. Chem. Rev. 2016, 116, 2170-2243.
https://doi.org/10.1021/acs.chemrev.5b00441

[13]. Coulembier, O.; Degee, P.; Hedrick, J. L.; Dubois, P. Prog. Polym. Sci. 2006, 31, 723-747.
https://doi.org/10.1016/j.progpolymsci.2006.08.004

[14]. Nyce, G. W.; Glauser, T.; Connor, E. F.; Moeck, A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2003, 125, 3046-3056.
https://doi.org/10.1021/ja021084+

[15]. Connor, E. F.; Nyce, G. W.; Myers, M.; Moeck, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 124, 914-915.
https://doi.org/10.1021/ja0173324

[16]. He, M.; Struble Justin, R.; Bode Jeffrey, W. J. Am. Chem. Soc. 2006, 128, 8418-8420.
https://doi.org/10.1021/ja062707c

[17]. Cheng, J.; Huang, Z.; Chi, Y. R. Angew. Chem. Int. Ed. 2013, 52, 8592-8596.
https://doi.org/10.1002/anie.201303247

[18]. Lee, A.; Younai, A.; Price, C. K.; Izquierdo, J.; Mishra, R. K.; Scheidt, K. A. J. Am. Chem. Soc. 2014, 136, 10589-10592.
https://doi.org/10.1021/ja505880r

[19]. Ryan, S. J.; Candish, L.; Lupton, D. W. Chem. Soc. Rev. 2013, 42, 4906-4917.
https://doi.org/10.1039/c3cs35522e

[20]. Ugai, T.; Tanaka, S.; Dokawa, S. Yakugaku Zasshi 1943, 64, 296-300.

[21]. Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726.
https://doi.org/10.1021/ja01547a064

[22]. Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem. Int. Ed. 2007, 46, 2988-3000.
https://doi.org/10.1002/anie.200603380

[23]. Johnson, J. S. Angew. Chem., Int. Ed. 2004, 43, 1326-1328.
https://doi.org/10.1002/anie.200301702

[24]. Hayat, F.; Kang, L.; Lee, C. Y.; Shin, D. Tetrahedron 2015, 71, 2945-2950.
https://doi.org/10.1016/j.tet.2015.03.023

[25]. Malik, N.; Zhang, Z.; Erhardt, P. J. Nat. Prod. 2015, 78, 2940-2947.
https://doi.org/10.1021/acs.jnatprod.5b00607

[26]. Siddiqui, S. A.; Narkhede, U. C.; Palimkar, S. S.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Tetrahedron 2005, 61, 3539-3546.
https://doi.org/10.1016/j.tet.2005.01.116

[27]. Shimakawa, Y.; Morikawa, T.; Sakaguchi, S. Tetrahedron Lett. 2010, 51, 1786-1789.
https://doi.org/10.1016/j.tetlet.2010.01.103

[28]. Joo, C.; Kang, S.; Kim, S. M.; Han, H.; Yang, J. W. Tetrahedron Lett. 2010, 51, 6006-6007.
https://doi.org/10.1016/j.tetlet.2010.09.028

[29]. Mirjalili, B. B. F.; Bamoniri, A.; Akbari, A. Chem. Heterocycl. Comp. 2011, 47, 487-491.
https://doi.org/10.1007/s10593-011-0785-1

[30]. Kadam, H. K.; Khan, S.; Kunkalkar, R. A.; Tilve, S. G. Tetrahedron Lett. 2013, 54, 1003-1007.
https://doi.org/10.1016/j.tetlet.2012.12.041

[31]. Li, J. J.; Norton, M. B.; Reinhard, E. J.; Anderson, G. D.; Gregory, S. A.; Isakson, P. C.; Koboldt, C. M.; Masferrer, J. L.; Perkins, W. E.; Seibert, K.; Zhang, Y.; Zweifel, B. S.; Reitz, D. B. J. Med. Chem. 1996, 39, 1846-1856.
https://doi.org/10.1021/jm950878e

[32]. Singh, D. P.; Kumar, R.; Singh, J. Eur. J. Med. Chem. 2009, 44, 1731-1736.
https://doi.org/10.1016/j.ejmech.2008.03.007

[33]. Muccioli, G. G.; Martin, D.; Scriba, G. K. E.; Poppitz, W.; Poupaert, J. H.; Wouters, J.; Lambert, D. M. J. Med. Chem. 2005, 48, 2509-2517.
https://doi.org/10.1021/jm049263k

[34]. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541.
https://doi.org/10.1021/ar030050j

[35]. Fevre, M.; Pinaud, J.; Gnanou, Y.; Vignolle, J.; Taton, D. Chem. Soc. Rev. 2013, 42, 2142-2172.
https://doi.org/10.1039/c2cs35383k

[36]. Iwamoto, K. -I.; Hamaya, M.; Hashimoto, N.; Kimura, H.; Suzuki, Y.; Sato, M. Tetrahedron Lett. 2006, 47, 7175-7177.
https://doi.org/10.1016/j.tetlet.2006.07.153

[37]. Hervert, B.; McCarthy, P. D.; Palencia, H. Tetrahedron Lett. 2014, 55, 133-136.
https://doi.org/10.1016/j.tetlet.2013.10.135

[38]. Broekemier, N. W.; Broekemier, N. C.; Short, R. T.; Palencia, H. Eur. J. Chem. 2014, 5(1), 162-166.
https://doi.org/10.5155/eurjchem.5.1.162-166.940

[39]. Liu, J.; Chen, J.; Zhao, J.; Zhao, Y.; Li, L.; Zhang, H. Synthesis-Stuttgart 2003, 2661-2666.

[40]. Delaude, L.; Szypa, M.; Demonceau, A.; Noels, A. F. Adv. Synth. Catal. 2002, 344 (6-7), 749-756.
https://doi.org/10.1002/1615-4169(200208)344:6/7<749::AID-ADSC749>3.0.CO;2-T

[41]. Amyes, T. L.; Diver, S. T.; Richard, J. P.; Rivas, F. M.; Toth, K., J. Am. Chem. Soc. 2004, 126 (13), 4366-4374.
https://doi.org/10.1021/ja039890j

[42]. Cai, G.; Feng, J.; Zhu, J.; Wilkie, C. A. Polym. Degrad. Stabil. 2014, 99, 204-210.
https://doi.org/10.1016/j.polymdegradstab.2013.11.004

[43]. Vora, H. U.; Lathrop, S. P.; Reynolds, N. T.; Kerr, M. S.; Read de Alaniz, J.; Rovis, T.; Chennamadhavuni, S.; Davies, H. M. L. Org. Synth. 2010, 87, 350-361.
https://doi.org/10.15227/orgsyn.087.0350

[44]. Rehbein, J.; Ruser, S. M.; Phan, J. Chem. Sci. 2015, 6(10), 6013-6018.
https://doi.org/10.1039/C5SC02186C

[45]. De Luca, L.; Mezzetti, A. Angew. Chem. Int. Ed. 2017, 56 (39), 11949-11953.
https://doi.org/10.1002/anie.201706261

[46]. Arifin, K.; Minggu, L. J.; Daud, W. R. W.; Yamin, B. M.; Daik, R.; Kassim, M. B. Spectrochim. Acta A 2014, 120, 208-215.
https://doi.org/10.1016/j.saa.2013.09.069

[47]. Myles, L.; Gathergood, N.; Connon, S. J. Chem. Commun. 2013, 49 (46), 5316-5318.
https://doi.org/10.1039/c3cc41588k

[48]. Iwamoto, K. -i.; Kimura, H.; Oike, M.; Sato, M. Org. Biomol. Chem. 2008, 6 (5), 912-915.
https://doi.org/10.1039/b719430g

[49]. Plummer, C. W.; Finke, P. E.; Mills, S. G.; Wang, J.; Tong, X.; Doss, G. A.; Fong, T. M.; Lao, J. Z.; Schaeffer, M. -T.; Chen, J.; Shen, C. P.; Stribling, D. S.; Shearman, L. P.; Strack, A. M.; Van der Ploeg, L. H. T. Bioorg. Med. Chem. Lett. 2005, 15(5), 1441-1446.
https://doi.org/10.1016/j.bmcl.2004.12.078

[50]. Procuranti, B.; Connon, S. J. Chem. Commun. 2007, 14, 1421-1423.
https://doi.org/10.1039/b618792g

[51]. Collett, C. J.; Massey, R. S.; Maguire, O. R.; Batsanov, A. S.; O'Donoghue, A. C.; Smith, A. D. Chem. Sci. 2013, 4, 1514-1522.
https://doi.org/10.1039/c2sc22137c

[52]. Haghshenas, P.; Gravel, M. Org. Lett. 2016, 18, 4518-4521.
https://doi.org/10.1021/acs.orglett.6b02123

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