Generic placeholder image

Current Microwave Chemistry

Author(s): Debasish Kundu*, Anup Roy, Subir Panja and Raj K. Singh

DOI: 10.2174/2213335607666200212101502

DownloadDownload PDF Flyer Cite As
Microwave-assisted Cobalt-copper Dual Catalyzed Ligand Free C-Se Cross-coupling

Page: [157 - 163] Pages: 7

  • * (Excluding Mailing and Handling)

Abstract

Background: Organoselenides are important building blocks of several biologically important molecules and natural products. Several protocols have been developed by chemists for their synthesis. Transition metal-catalyzed cross-coupling is a powerful tool for this purpose in the last two decades. Various transition metal catalysts e.g. Pd, Ni, Cu, In etc. have been used for performing C-Se cross-coupling in the presence or absence of ligands.

Objective: Development of a sustainable protocol for transition metal-catalyzed C-Se cross-coupling is the main objective of this research. Recently, Cobalt has been applied as a cheap and sustainable transition metal catalyst in several organic reactions. This protocol is focused on applying cobalt salt as a catalyst for performing C-Se cross-coupling for the first time.

Methods: Co(acac)2 has been successfully employed for performing Se-arylations in the presence of CuI, which acts as a co-catalyst under microwave irradiation. NMP was used as solvent and KOH as a reductant in this reaction.

Results: Both iodo-and bromoarenes have been used to perform C-Se cross-coupling with diaryl diselenide under this Co/Cu dual catalytic system. The reaction was successful with both electrondonating and withdrawing groups in ortho-, meta-, and para-positions in the aromatic ring of Bromo and iodoarenes.

Conclusion: This is an effective protocol for the preparation of organoselenides, catalyzed by cobalt in the presence of copper. The mechanism has been established by several experimental techniques.

Keywords: Cobalt, copper, cross-coupling, organoselenides, green chemistry, dual catalysis.

Graphical Abstract

[1]
Mugesh, G.; du Mont, W.W.; Sies, H. Chemistry of biologically important synthetic organoselenium compounds. Chem. Rev., 2001, 101(7), 2125-2179.
[http://dx.doi.org/10.1021/cr000426w] [PMID: 11710243]
[2]
Nogueira, C.W.; Zeni, G.; Rocha, J.B.T. Organoselenium and organotellurium compounds: toxicology and pharmacology. Chem. Rev., 2004, 104(12), 6255-6285.
[http://dx.doi.org/10.1021/cr0406559] [PMID: 15584701]
[3]
Okamoto, Y. The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S; Rappoport, Z., Ed.; Wiley: Chichester, U. K., 1986, Vol. 1, p. 10.
[4]
Rotruck, J.T.; Pope, A.L.; Ganther, H.E.; Swanson, A.B.; Hafeman, D.G.; Hoekstra, W.G. Selenium: biochemical role as a component of glutathione peroxidase. Science, 1973, 179(4073), 588-590.
[http://dx.doi.org/10.1126/science.179.4073.588] [PMID: 4686466]
[5]
(a)Beletskaya, I.P.; Sigeev, A.S.; Peregudov, A.S.; Petrovskii, P.V. New approaches to the synthesis of unsymmetrical diaryl selenides J. Org. Chem.,, 2000, 605, 96-101.
[http://dx.doi.org/10.1016/S0022-328X(00)00265-5]
(b)Zhao, H.; Hao, W.; Xi, Z.; Cai, M. Palladium-catalyzed crosscoupling of PhSeSnBu3 with aryl and alkyl halides in ionic liquids: a practical synthetic method of diorganyl selenides. New J. Chem, 2011, 35, 2661-2665.
[http://dx.doi.org/10.1039/c1nj20514e]
(c)Senol, E.; Scattolin, T.; Schoenebeck, F. selenolation of aryl iodides and bromides enabled by a bench-stable PdI dimer Chemistry, 2019, 25(40), 9419-9422.
[http://dx.doi.org/10.1002/chem.201900951] [PMID: 30913326]
(d)Grenader, K.; Schüpbach, B.; Peters, A.; Kümmel, O.; Halter, O.; Terfort, A. Catalytic C-Se bond formation under very mild conditions for the two-step, one-pot synthesis of aryl selenoacetates Adv. Synth. Catal, 2012, 354, 2653.
[http://dx.doi.org/10.1002/adsc.201200486]
(e)Bonaterra, M.; Rossi, R.A.; Martín, S.E. Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1- Naphthyl Triflate Organometallics, 2009, 28, 933-936.
[http://dx.doi.org/10.1021/om8009816]
(f)Bonaterra, M.; Martín, S.E.; Rossi, R.A. Palladium-catalyzed phenyl-selenylation with n-Bu3SnSePh in one-pot two-step reactions Tetrahedron Lett, 2006, 47, 3511-3515.
[http://dx.doi.org/10.1016/j.tetlet.2006.03.106]
(g)Wallner, O.A.; Szabó, K.J. Employment of palladium pincer-complexes in phenylselenylation of organohalides. J. Org. Chem., 2005, 70(23), 9215-9221.
[http://dx.doi.org/10.1021/jo051266x] [PMID: 16268593]
[6]
Wang, M.; Ren, K.; Wang, L. Iron-Catalyzed ligand free carbonselenium (or Tellurium) coupling of arylboronic acids with diselenides and ditellurides. Adv. Synth. Catal., 2009, 351, 1586.
[http://dx.doi.org/10.1002/adsc.200900095]
[7]
Cristau, H.J.; Chaband, B.; Labaudiniere, R.; Christol, H. Synthesis of aryl phenyl and heteroaryl phenyl selenides by nickel (II)-catalyzed arylation of sodium benzeneselenolate. Organometallics, 1985, 4, 657.
[http://dx.doi.org/10.1021/om00123a007]
[8]
(a)Dandapat, A.; Korupalli, C.; Prasad, D.J.C.; Singh, R.; Sekar, G. An efficient copper (I) iodide catalyzed synthesis of diaryl selenides through CAr-Se bond formation using solvent acetonitrile as ligand. Synthesis, 2011, 2297-2302.
(b)Li, Y.; Wang, H.; Li, X.; Chen, T.; Zhao, D. CuS/Fe: a novel and highly efficient catalyst system for coupling reaction of aryl halides with diaryl diselenides Tetrahedron, 2010, 66, 8583-8586.
[http://dx.doi.org/10.1016/j.tet.2010.09.061]
(c)Wang, L.; Wang, M.; Huang, F. A simple copper salt-catalyzed synthesis of unsymmetrical diaryl selenides and tellurides from arylboronic acids with diphenyl diselenide and ditelluride. Synlett, 2005, 2007-2010.
(d)Singh, D.; Alberto, E.E.; Rodrigues, O.E.D.; Braga, A.L. Eco-friendly cross-coupling of diaryl diselenides with aryl and alkyl bromides catalyzed by CuO nanopowder in ionic liquid. Green Chem, 2009, 11, 1521-1524.
[http://dx.doi.org/10.1039/b916266f]
(e)Chatterjee, T.; Ranu, B.C. Solvent-controlled halo-selective selenylation of aryl halides catalyzed by Cu(II) supported on Al2O3. A general protocol for the synthesis of unsymmetrical organo mono- and bis-selenides. J. Org. Chem., 2013, 78(14), 7145-7153.
[http://dx.doi.org/10.1021/jo401062k] [PMID: 23786642]
[9]
(a)Kundu, D.; Mukherjee, N.; Ranu, B. C A general and green procedure for the synthesis of organochalcogenides by CuFe2O4 nanoparticle catalysed coupling of organoboronic acids and dichalcogenides in PEG-400 RSc Adv., 2013, 3, 117-125.
[http://dx.doi.org/10.1039/C2RA22415A]
(b)Didehban, K.; Vessally, E.; Hosseinian, A.; Edjlali, E.; Khosroshahi, E.S. Nano catalysts for C-Se crosscoupling reactions RSC Advances, 2018, 8, 291-301.
[http://dx.doi.org/10.1039/C7RA12663H]
(c)Swapna, K.; Murthy, S.N.; Durga Negeswar, Y.V. Magnetically separable and reusable copper ferrite nanoparticles for cross-coupling of aryl halides with diphenyl diselenide. Eur. J. Org. Chem., 2011, 10, 1940-1946.
[http://dx.doi.org/10.1002/ejoc.201001639]
[10]
Wong, Y-C.; Jayanth, T.T.; Cheng, C.H. Cobalt-catalyzed aryl-sulfur bond formation. Org. Lett., 2006, 8(24), 5613-5616.
[http://dx.doi.org/10.1021/ol062344l] [PMID: 17107085]
[11]
Lan, M-T.; Wu, W-Y.; Huang, S-H.; Luo, K-L.; Tsai, F-Y. Reusable and efficient CoCl2 •6H2O/cationic 2,2′-bipyridyl system-catalyzed S-arylation of aryl halides with thiols in water under air. RSC Advances, 2011, 1, 1751-1755.
[http://dx.doi.org/10.1039/c1ra00406a]
[12]
Teo, Y-C.; Chua, G-L. Cobalt-catalyzed N-arylation of nitrogen nucleophiles in water. Chemistry, 2009, 15(13), 3072-3075.
[http://dx.doi.org/10.1002/chem.200802483] [PMID: 19219864]
[13]
Peng, J.; Zong, C.; Ye, M.; Chen, T.; Gao, D.; Wang, Y.; Chen, C. Direct transition-metal-free intramolecular C-O bond formation: synthesis of benzoxazole derivatives. Org. Biomol. Chem., 2011, 9(4), 1225-1230.
[http://dx.doi.org/10.1039/C0OB00454E] [PMID: 21186392]
[14]
Kundu, D.; Tripathy, M.; Maity, P.; Ranu, B.C. Cobalt-catalyzed intermolecular C(sp(2))-O cross-coupling. Chemistry, 2015, 21(24), 8727-8732.
[http://dx.doi.org/10.1002/chem.201500058] [PMID: 25926040]
[15]
Ghosh, T.; Maity, P.; Kundu, D.; Ranu, B.C. Cobalt catalysed, copper assisted C(sp2)–P cross coupling. New J. Chem., 2016, 40, 9556-9564.
[http://dx.doi.org/10.1039/C6NJ02247B]
[16]
Wang, T.; Chen, J.; Wang, J.; Xu, S.; Lin, A.; Yao, H.; Jiang, S.; Xu, J. Cobalt-catalyzed carbon-sulfur/selenium bond formation: synthesis of benzo[b]thio/selenophene-fused imidazo[1,2-a]pyridines. Org. Biomol. Chem., 2018, 16(20), 3721-3725.
[http://dx.doi.org/10.1039/C8OB00743H] [PMID: 29737996]
[17]
King, A.E.; Ryland, B.L.; Brunold, T.C.; Stahl, S.S. Kinetic and spectroscopic studies of aerobic copper(II)-catalyzed methoxylation of arylboronic esters and insights into aryl transmetalation to copper(II). Organometallics, 2012, 31(22), 7948-7957.
[http://dx.doi.org/10.1021/om300586p] [PMID: 23204631]
[18]
(a)Bhattacharjee, M.N.; Chaudhuri, M.K.; Ghosh, S.K.; Hiese, Z.; Roy, N. Direct synthesis of bis(acetylacetonato)nickel(II) dihydrate and isolation of α,α,β,β-tetra-acetylethane as the oxidation product of acetylacetone J. Chem. Soc. Dalton Trans., 1983, 2561-2562.
[http://dx.doi.org/10.1039/DT9830002561]
(b)Kundu, D.; Maity, P.; Ranu, B.C. Copper-assisted nickel catalyzed ligand-free C(sp2)-O cross-coupling of vinyl halides and phenols. Org. Lett., 2014, 16(4), 1040-1043.
[http://dx.doi.org/10.1021/ol500134p] [PMID: 24502267]
[19]
Mukherjee, N.; Chatterjee, T.; Ranu, B.C. Reaction under ball-milling: solvent-, ligand-, and metal-free synthesis of unsymmetrical diaryl chalcogenides. J. Org. Chem., 2013, 78(21), 11110-11114.
[http://dx.doi.org/10.1021/jo402071b] [PMID: 24116379]