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.
Graphical Abstract
[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]
[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]
[http://dx.doi.org/10.1021/ja005701a] [PMID: 11456693]
(b)Luque, R.; Baruwati, R.-S Green Chem., 2010, 12(9), 1540-1543.
[http://dx.doi.org/10.1039/c0gc00083c]
(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]
[http://dx.doi.org/10.1055/s-0036-1591602]
[http://dx.doi.org/10.1002/ange.200905626]
(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]
[http://dx.doi.org/10.1016/j.catcom.2009.04.002]
(b)Ciric, A.; Mathey, F. Organometallics, 2010, 29(21), 4785-4786.
[http://dx.doi.org/10.1021/om100423r]
[http://dx.doi.org/10.1002/ejoc.201001729]
(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]
[http://dx.doi.org/10.1021/jo00970a013]
(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.
[http://dx.doi.org/10.1002/ejoc.201001729]
[http://dx.doi.org/10.1002/ejoc.201100994]
[http://dx.doi.org/10.1039/c3gc40753e]
[http://dx.doi.org/10.1016/j.apcata.2013.10.048]
[http://dx.doi.org/10.1039/c4gc00056k]
[http://dx.doi.org/10.1055/s-0036-1590808]
[http://dx.doi.org/10.1007/s10562-018-2321-8]
(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.
[http://dx.doi.org/10.1016/j.tet.2015.12.006]
[http://dx.doi.org/10.1016/j.jcat.2013.06.017]
[http://dx.doi.org/10.1007/BF00766213]
[http://dx.doi.org/10.1002/slct.201801714]
[http://dx.doi.org/10.1039/C2GC36455G]
[http://dx.doi.org/10.1002/slct.201601986]