2,5-Dihydroxyterephthalic Acid Accelerated Cu(NO3)2.3H2O-Catalyzed Homocoupling Reaction of Arylboronic Acids

Author(s): Fengtian Wu, Chenlong Nan, Jianwei Xie, Mingyang Ma*

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 11 , 2020

Become EABM
Become Reviewer
Call for Editor

Graphical Abstract:


A catalyst system derived from commercially available Cu(NO3)2.3H2O and 2,5- dihydroxyterephthalic acid is applied to the homocoupling reaction of arylboronic acids. This transformation provides a convenient approach to symmetrical biaryls with good to excellent yields (39%- 95%), and exhibits good functional group compatibility. Furthermore, biaryl can be prepared in gram quantities in good yield.

Keywords: Arylboronic acid, biaryl, ligand, copper, homocoupling reaction, acid.

(a)Kozlowski, M.C.; Morgan, B.J.; Linton, E.C. Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling. Chem. Soc. Rev, 2009, 38(11), 3193-3207.
[http://dx.doi.org/10.1039/b821092f] [PMID: 19847351]
(b)Singh, F.V.; Vatsyayan, R.; Roy, U.; Goel, A. Arylanthranilodinitriles: a new biaryl class of antileishmanial agents. Bioorg. Med. Chem. Lett., 2006, 16(10), 2734-2737.
[http://dx.doi.org/10.1016/j.bmcl.2006.02.012] [PMID: 16503140]
(a)Nelson, R.A.; Pope, J.A., Jr; Luedemann, G.M.; McDaniel, L.E.; Schaffner, C.P. Crisamicin A, a new antibiotic from Micromonospora. I. Taxonomy of the producing strain, fermentation, isolation, physico-chemical characterization and antimicrobial properties J. Antibiot. (Tokyo), 1986, 39(3), 335-344.
[http://dx.doi.org/10.7164/antibiotics.39.335] [PMID: 3754547]
(b)Ezkai, M.; Iwami, M.; Yamashita, M.; Hashimoto, S.; Komori, T.; Umehara, K.; Mine, Y.; Kohsaka, M.; Aoki, H. J. Antibiot. (Tokyo), 1985, 38(11), 1453-1461.
[http://dx.doi.org/10.7164/antibiotics.38.1453] [PMID: 3841122]
(a)McFarland, S.A.; Finney, N.S. Fluorescent chemosensors based on conformational restriction of a biaryl fluorophore. J. Am. Chem. Soc, 2001, 123(6), 1260-1261.
[http://dx.doi.org/10.1021/ja005701a] [PMID: 11456693]
(b)Luque, R.; Baruwati, R.-S Green Chem., 2010, 12(9), 1540-1543.
(c)Wencel-Delord, J.; Panossian, A.; Leroux, F.R.; Colobert, F. Recent advances and new concepts for the synthesis of axially stereoenriched biaryls. Chem. Soc. Rev., 2015, 44(11), 3418-3430.
[http://dx.doi.org/10.1039/C5CS00012B] [PMID: 25904287]
Ostrowska, S.; Rogalski, S.; Lorkowski, J.; Walkowiak, J. Synlett, 2018, 29, 1735-1740.
(a)Jin, M-J.; Lee, D-H. Angew. Chem. Int. Ed., 2010, 49(7), 1137-1140.
(b)Gurung, S.K.; Thapa, S.; Kafle, A.; Dickie, D.A.; Giri, R. Copper-catalyzed Suzuki-Miyaura coupling of arylboronate esters: transmetalation with (PN)CuF and identification of intermediates. Org. Lett., 2014, 16(4), 1264-1267.
[http://dx.doi.org/10.1021/ol500310u] [PMID: 24499358]
(a)Mu, B.; Li, T.; Fu, Z.; Wu, Y. Catal. Commun., 2009, 10(11), 1497-1501.
(b)Ciric, A.; Mathey, F. Organometallics, 2010, 29(21), 4785-4786.
(a)Cheng, G.; Luo, M. Eur. J. Org. Chem., 2011, 13, 2519-2523.
(b)Lan, J-B.; Zhang, G-L.; Yu, X-Q.; You, J-S.; Chen, L.; Yan, M.; Xie, R-G. Synlett, 2004, 6, 1095-1097.
(c)Demir, A.S.; Reis, O.; Emrullahoglu, M. Role of copper species in the oxidative dimerization of arylboronic acids: synthesis of symmetrical biaryls. J. Org. Chem., 2003, 68(26), 10130-10134.
[http://dx.doi.org/10.1021/jo034680a] [PMID: 14682710]
(a)Roling, P.V.; Rausch, M.D. J. Org. Chem., 1972, 37(5), 729-732.
(b)Wang, W.; Shi, X.; Wang, S.; Van Hove, M.A.; Lin, N. Singlemolecule resolution of an organometallic intermediate in a surfacesupported Ullmann coupling reaction. J. Am. Chem. Soc., 2011, 133(34), 13264-13267.
[http://dx.doi.org/10.1021/ja204956b] [PMID: 21761920]
(c)Ullmann, F. Ber. Dtsch. Chem. Ges., 1903, 36(1), 2389-2391.
Cheng, G.; Luo, M. Eur. J. Org. Chem., 2011, 13, 2519-2523.
Kaboudin, B.; Abedi, Y.; Yokomatsu, T. Eur. J. Org. Chem., 2011, 33, 6656-6662.
Kaboudin, B.; Mostafalua, R.; Yokomatsu, T. Green Chem., 2013, 15(8), 2266-2274.
Dar, B.A.; Singh, S.; Pandey, N.; Singh, A.P.; Sharma, P.; Lazar, A.; Sharma, M.; Vishwakarma, R.A.; Singh, B. Appl. Catal. A Gen., 2014, 470, 232-238.
Puthiaraj, P.; Suresha, P.; Pitchumani, K. Green Chem., 2014, 16(5), 2865-2875.
Cao, Y-N.; Tian, X-C.; Chen, X-X.; Yao, Y-X.; Gao, F.; Zhou, X-L. Synlett, 2017, 28, 601-606.
(a)Wang, X.; Meng, F.; Zhang, J.; Xie, J.; Dai, B. Catal. Lett., 2018, 148(4), 1142-1149.
(b)Li, Z.; Meng, F.; Zhang, J.; Xie, J.; Dai, B. Efficient and recyclable copper-based MOF-catalyzed N-arylation of N-containing heterocycles with aryliodides. Org. Biomol. Chem., 2016, 14(46), 10861-10865.
[http://dx.doi.org/10.1039/C6OB02068B] [PMID: 27808320]
(c)Liu, X-G.; Li, Z-H.; Xie, J-W.; Liu, P.; Zhang, J.; Dai, B. Tetrahedron, 2016, 75(5), 653-657.
Li, G.; Jiang, D.; Liu, C.; Yu, C.; Jin, R. J. Catal., 2013, 306, 177-183.
Lee, G.S.; Ma, J.J.; Rocke, S.C.; Garcés, J.M. Catal. Lett., 1989, 2(4), 243-247.
Xu, X.; Gao, S.; Chen, W.; Gao, Z.; Luo, J. ChemistrySelect, 2018, 3(31), 8863-8866.
Nasir, B.R.B.; Varma, R.S. Green Chem., 2013, 15(2), 398-417.
Kar, B.; Bardhan, S.; Ghosh, P.; Ganguly, B.; Kundu, K.; Sarkar, S.; Paul, B.K.; Das, S. ChemistrySelect, 2017, 2(3), 1079-1088.

Rights & PermissionsPrintExport Cite as

Article Details

Year: 2020
Page: [877 - 883]
Pages: 7
DOI: 10.2174/1570178617666200210110041
Price: $65

Article Metrics

PDF: 26
PRC: 1