Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Letter Article

Aerobic Oxidation of Aldehydes to Carboxylic Acids Catalyzed by Recyclable Ag/C3N4 Catalyst

Author(s): Min Yu, Chaolong Wu, Li Zhou, Li Zhu* and Xiaoquan Yao*

Volume 18, Issue 3, 2021

Published on: 07 August, 2020

Page: [167 - 175] Pages: 9

DOI: 10.2174/1570178617999200807210137

Price: $65

Abstract

The oxidation of aldehydes is an efficient methodology for the synthesis of carboxylic acids. Herein we hope to report a simple, efficient and recyclable protocol for aerobic oxidation of aldehydes to carboxylic acid by using C3N4 supported silver nanoparticles (Ag/C3N4) as a catalyst in aqueous solution under mild conditions. Under standard conditions, the corresponding carboxylic acids can be obtained in good to excellent yields. In addition, Ag/C3N4 is convenient for recovery and could be reused three times with satisfactory yields.

Keywords: Ag/C3N4, silver nanoparticles, aerobic oxidation, aldehydes, carboxylic acids, water.

Next »
Graphical Abstract
[1]
Crabb, D.W.; Matsumoto, M.; Chang, D.; You, M. Proc. Nutr. Soc., 2004, 63(1), 49-63.
[http://dx.doi.org/10.1079/PNS2003327] [PMID: 15099407]
[2]
(a)Shao, Z.H.; Wang, Y.J.; Liu, Y.Q.; Wang, Q.; Fu, X.L.; Liu, Q. Org. Chem. Front., 2018, 5, 1248-1256.
[http://dx.doi.org/10.1039/C8QO00023A]
(b)Gianetti, T.L.; Annen, S.P.; Santiso-Quinones, G.; Reiher, M.; Driess, M.; Grützmacher, H. Angew. Chem. Int. Ed. 2016 55, 1854-1858.,
[http://dx.doi.org/10.1002/anie.201509288]
(c)Santilli, C.; Makarov, I.S.; Fristrup, P.; Madsen, R. J. Org. Chem., 2016, 81(20), 9931-9938.
[http://dx.doi.org/10.1021/acs.joc.6b02105] [PMID: 27685175]
(d)Davis, S.E.; Ide, M.S.; Davis, R.J. Green Chem, 2013, 15, 17-45.
[http://dx.doi.org/10.1039/C2GC36441G.]
(e)Naimi-Jamal, M.R.; Hamzeali, H.; Mokhtari, J.; Boy, J.; Kaupp, G. ChemSusChem, 2009, 2(1), 83-88.
[http://dx.doi.org/10.1002/cssc.200800193] [PMID: 19115303]
(f)Zweifel, T.; Naubron, J.V.; Grützmacher, H. Angew. Chem. Int. Ed., 2009, 48, 559-563.,
[http://dx.doi.org/10.1002/anie.200804757]
(g)Patel, S.; Mishra, B.K. Tetrahedron, 2007, 63, 4367-4406,
[http://dx.doi.org/10.1016/j.tet.2007.02.073]
(h)Mazitschek, R.; Mülbaier, M.; Giannis, A. Angew. Chem. Int. Ed., 2002, 41, 4059-4061.
[http://dx.doi.org/10.1002/1521-3773(20021104)41:21<4059:AID-ANIE4059>3.0.CO;2-R]
[3]
(a)Shaikh, T.M.; Hong, F.E. Tetrahedron, 2013, 69, 8929-8935.
[http://dx.doi.org/10.1016/j.tet.2013.07.101]
(b)Rafiee, M.; Konz, Z.M.; Graaf, M.D.; Koolman, H.F.; Stahl, S.S. ACS Catal., 2018, 8, 6738-6744.
[http://dx.doi.org/10.1021/acscatal.8b01640]
(c)Liu, K.J.; Fu, Y.L.; Xie, L.Y.; Wu, C.; He, W.B.; Peng, S.; Wang, Z.; Bao, W.H.; Cao, Z.; Xu, X.H.; He, W.M. ACS Sustain. Chem.& Eng., 2018, 6, 4916-4921.
[http://dx.doi.org/10.1021/acssuschemeng.7b04400]
[4]
(a)Shriner, R.L.; Kleiderer, E.C. Org. Synth., 1930, 2, 538.
(b)Ruhoff, J.R. Org. Synth., 1936, 2, 315.
[5]
Sandborn, L.T. Org. Synth., 1921, 1, 340.
[6]
Hunsen, M. Synthesis, 2005, 2487-2490.
[http://dx.doi.org/10.1055/s-2005-872085]
[7]
Travis, B.R.; Sivakumar, M.; Hollist, G.O.; Borhan, B. Org. Lett., 2003, 5(7), 1031-1034.
[http://dx.doi.org/10.1021/ol0340078] [PMID: 12659566]
[8]
Fehling, H. Ann. Chem. Pharm., 1849, 72, 106-113.
[http://dx.doi.org/10.1002/jlac.18490720112]
[9]
Oshima, K.; Tollens, B. Ber. Dtsch. Chem. Ges., 1901, 34, 1425-1426.
[http://dx.doi.org/10.1002/cber.19010340212]
[10]
(a)Liang, Y.F.; Jiao, N. Acc. Chem. Res., 2017, 50(7), 1640-1653.
[http://dx.doi.org/10.1021/acs.accounts.7b00108] [PMID: 28636366]
(b)Mallat, T.; Baiker, A. Chem. Rev., 2004, 104(6), 3037-3058.,
[http://dx.doi.org/10.1021/cr0200116] [PMID: 15186187]
(c)Ahmed, M.S.; Mannel, D.S.; Root, T.W.; Stahl, S.S. Org. Process Res. Dev., 2017, 21, 1388-1393.
[http://dx.doi.org/10.1021/acs.oprd.7b00223]
(d)Jiang, X.; Zhang, J.; Ma, S. J. Am. Chem. Soc., 2016, 138(27), 8344-8347.
[http://dx.doi.org/10.1021/jacs.6b03948] [PMID: 27304226]
(e)Han, L.; Xing, P.; Jiang, B. Org. Lett., 2014, 16(13), 3428-3431.,
[http://dx.doi.org//10.1021/ol501353q] [PMID: 24937233]
(f)Kim, S.M.; Kim, D.W.; Yang, J.W. Org. Lett., 2014, 16(11), 2876-2879.,
[http://dx.doi.org/10.1021/ol501012f] [PMID: 24831968]
(g)Zope, B.N.; Hibbitts, D.D.; Neurock, M.; Davis, R. J. Sci., 2010, 330, 74-78.
[11]
Yoshida, M.; Katagiri, Y.; Zhu, W.B.; Shishido, K. Org. Biomol. Chem., 2009, 7(19), 4062-4066.
[http://dx.doi.org/10.1039/b910187j] [PMID: 19763312]
[12]
(a)Lu, T.L.; Du, Z.T.; Liu, J.X.; Ma, H.; Xu, J. Green Chem., 2013, 15, 2215-2221.,
[http://dx.doi.org/10.1039/c3gc40730f]
(b)Rass, H.A.; Essayem, N.; Besson, M. Green Chem., 2013, 15, 2240-2251,
[http://dx.doi.org/10.1039/c3gc40727f]
(c)Yamada, Y.M.A.; Arakawa, T.; Hocke, H.; Uozumi, Y. Angew. Chem., 2007, 46, 704-706.,
[http://dx.doi.org/10.1002/anie.200603900]
(d)Stahl, S.S. Science, 2005, 309(5742), 1824-1826.,
[http://dx.doi.org/10.1126/science.1114666] [PMID: 16166508]
(e)Brink, G.J.; Arends, I.W.; Sheldon, R.A. Science, 2000, 287, 1636-1639.
[http://dx.doi.org/10.1126/science.287.5458.1636] [PMID: 10698735]
[13]
Liu, M.; Wang, H.; Zeng, H.; Li, C. J. Sci. Adv., 2015, 1e1500020,
[http://dx.doi.org/10.1126/sciadv.1500020]
[14]
Liu, M.X.; Li, C-J. Angew. Chem. Int. Ed., 2016, 55, 10806-10810.
[http://dx.doi.org/10.1002/anie.201604847]
[15]
Dai, P.F.; Qu, J.P.; Kang, Y.B. Org. Lett., 2019, 21(5), 1393-1396.
[http://dx.doi.org/10.1021/acs.orglett.9b00101] [PMID: 30763111]
[16]
Tian, Q.; Shi, D.; Sha, Y. Molecules, 2008, 13(4), 948-957.
[http://dx.doi.org/10.3390/molecules13040948] [PMID: 18463597]
[17]
ACS Catal., 2016, 6, 7979-7988.
[18]
(a)Xu, H.; Wu, K.Y.; Tian, J.; Zhu, L.; Yao, X. Green Chem., 2018, 20, 793-797.,
[http://dx.doi.org/10.1039/C7GC03120C]
(b)Xu, H.; Wang, J.; Wang, P.; Niu, X.Y.; Luo, Y.D.; Zhu, L.; Yao, X. RSC Advances, 2018, 8, 32942-32947.,
[http://dx.doi.org/10.1039/C8RA06613B]
(c)Yu, M.; Liu, G.X.; Han, C.Y.; Zhu, L.; Yao, X. Lett. Org. Chem., 2018, 15, 70-77.
[http://dx.doi.org/10.2174/1570178615666180110161450]
(d)Wang, X.W.; Wu, C.L.; Sun, Y.W.; Yao, X. Tetrahedron Lett., 2017, 58, 3164-3167,
[http://dx.doi.org/10.1016/j.tetlet.2017.07.001]
(e)Xu, D.J.; Meng, L.C.; Xu, H.; Yao, X. Youji Huaxue, 2017, 37, 1205-1212.,
[http://dx.doi.org/10.6023/cjoc201701051]
(f)Wang, Y.; Wu, C.L.; Nie, S.J.; Xu, D.J.; Yu, M.; Yao, X. Tetrahedron Lett., 2015, 56, 6827-6832.,
[http://dx.doi.org/10.1016/j.tetlet.2015.10.078]
(g)Zeng, S.W.; Xu, S.; Wang, Y.; Yu, M.; Zhu, L.; Yao, X. Youji Huaxue, 2015, 35, 827-834.,
[http://dx.doi.org/10.6023/cjoc201412045]
(h)Lv, W.; Tian, J.; Deng, N.; Wang, Y.; Zhu, X.S.; Yao, X. Tetrahedron Lett., 2015, 56, 1312-1316.
[http://dx.doi.org/10.1016/j.tetlet.2015.01.177]
(i)Han, C.; Yu, M.; Sun, W.; Yao, X. Synlett, 2011, 2363-2368.
[19]
(a)Wang, L.; Yu, M.; Wu, C.L.; Deng, N.; Wang, C.; Yao, X. Adv. Synth. Catal., 2016, 358, 2631-2641.,
[http://dx.doi.org/10.1002/adsc.201600138]
(b)Wang, C.; Deng, N.; Wang, L.L.; Xu, D.J.; Yao, X. Youji Huaxue, 2016, 36, 1034-1043.,
[http://dx.doi.org/10.6023/cjoc201512018]
(c)Yu, M.; Wang, Y.; Sun, W.J.; Yao, X. Adv. Synth. Catal., 2012, 354, 71-76.,
[http://dx.doi.org/10.1002/adsc.201100518]
(d)Yu, M.; Lin, M.D.; Han, C.Y.; Zhu, L.; Li, C-J.; Yao, X. Tetrahedron Lett., 2010, 51, 6722-6725.
[http://dx.doi.org/10.1016/j.tetlet.2010.10.065]
[20]
(a)Yu, M.; Wang, Y.; Li, C-J.; Yao, X. etrahedron Lett., 2009, 50, 6791-6794.,
[http://dx.doi.org/10.1016/j.tetlet.2009.09.095]
(b)Yao, X.; Li, C-J. Org. Lett., 2006, 8(9), 1953-1955,
[http://dx.doi.org/10.1021/ol060645p] [PMID: 16623593]
(c)Yao, X.; Li, C-J. Org. Lett., 2005, 7(20), 4395-4398.
[http://dx.doi.org/10.1021/ol051575+] [PMID: 16178542]
[21]
(a)Ahmadi, M.; Mistry, H.; Roldan Cuenya, B. J. Phys. Chem. Lett., 2016, 7(17), 3519-3533.
[http://dx.doi.org/10.1021/acs.jpclett.6b01198] [PMID: 27530730]
(b)Morgan, K.; Goguet, A.; Hardacre, C. ACS Catal., 2015, 5, 3430-3445.,
[http://dx.doi.org/10.1021/acscatal.5b00535]
(c)Molnár, Á.A. Coordin. Chem. Rev., 2017, 349, 1-65.
[22]
(a)Zavras, A.; Khairallah, G.N.; Connell, T.U.; White, J.M.; Edwards, A.J.; Mulder, R.J.; Donnelly, P.S.; O’Hair, R.A.J. Inorg. Chem., 2014, 53(14), 7429-7437,
[http://dx.doi.org/10.1021/ic5007499] [PMID: 24991699]
(b)Liu, C.W.; Chang, H.W.; Sarkar, B.; Saillard, J.Y.; Kahlal, S.; Wu, Y.Y. Inorg. Chem., 2010, 49(2), 468-475.
[http://dx.doi.org/10.1021/ic901408n] [PMID: 20025253]
[23]
Nie, S.J.; Wang, J.; Huang, X.; Niu, X.Y.; Zhu, L. X. ACS Appl. Nano Mater., 2018, 1(12), 6567-6574,,
[http://dx.doi.org/10.1021/acsanm.8b01607,]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy