Recent Advances in C-C and C-N Bond Forming Reactions Catalysed by Polystyrene-Supported Copper Complexes

. 2017 May 24 ; 22 (6) : . [epub] 20170524

Jazyk angličtina Země Švýcarsko Médium electronic

Typ dokumentu časopisecké články, přehledy

Perzistentní odkaz   https://www.medvik.cz/link/pmid28538656

This present mini-review covers recently published results on Cu(I) and Cu(II) complexes immobilized on polystyrene carriers, which are used as heterogeneous, eco-friendly reusable catalysts applied for carbon-carbon and carbon-nitrogen forming reactions. Recent advances and trends in this area are demonstrated in the examples of oxidative homocoupling of terminal alkynes, the synthesis of propargylamines, nitroaldolization reactions, azide alkyne cycloaddition, N-arylation of nitrogen containing compounds, aza-Michael additions, asymmetric Friedel-Crafts reactions, asymmetric Mukaiyama aldol reactions, and asymmetric 1,3-dipolar cycloaddition of azomethine ylides. The type of polystyrene matrix used for the immobilization of complexes is discussed in this paper, and particularly, the efficiency of the catalysts from the point of view of the overall reaction yield, and possible enantioselectivity and potential reusing, is reviewed.

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Van Santen R., Khoe D., Vermeer B. 2030 Technology that will Change the World. Oxford University Press; New York, NY, USA: 2010. Sustainable materials.

Anastas P.T., Warner J.C. Green Chemistry: Theory and Practice. Oxford University Press; New York, NY, USA: 2000. Tools of Green Chemistry.

Cozzi F. Immobilization of organic catalysts: When, why, and how. Adv. Synth. Catal. 2006;348:1367–1390. doi: 10.1002/adsc.200606096. DOI

Benaglia M. Recoverable and Recyclable Catalysts. John Wiley & Sons; Wiltshire, UK: 2009. Insoluble Resin-supported Catalysts.

Jimeno C., Sayalero S., Pericàs M.A. Covalent Heterogenization of Asymmetric Catalysts on Polymers and Nanoparticles. In: Barbaro P., Liguori F., editors. Heterogenized Homogenous Catalysts for Fine Chemicals Production: Materials and Processes. Springer Science and Business Media; Dordrecht, the Netherlands: 2010.

Merrifield R.B.J. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 1963;85:2149–2154. doi: 10.1021/ja00897a025. DOI

Kristensen T.E., Hansen T. Polymer-supported chiral organocatalysts: Synthetic strategies for the road towards affordable polymeric immobilization. Eur. J. Org. Chem. 2010:3179–3204. doi: 10.1002/ejoc.201000319. DOI

Glaser C. Beiträge zur Kenntniss des Acetenylbenzols. Ber. Dtsch. Chem. Ges. 1869;2:422–424. doi: 10.1002/cber.186900201183. DOI

Sindhu K.S., Anilkumar G. Recent advances and applications of Glaser coupling employing greener protocols. RSC Adv. 2014;4:27867–27887. doi: 10.1039/c4ra02416h. DOI

Yan S., Pan S., Osako T., Uozumi Y. Recyclable polystyrene-supported copper catalysts for the aerobic oxidative homocoupling of terminal alkynes. Synlett. 2016;27:1232–1236. doi: 10.1002/chin.201639051. DOI

Sun Q., Lv Z., Du Y., Wu Q., Wang L., Zhu L., Meng X., Chen W., Xiao F.-S. Recyclable porous polymer-supported copper catalysts for Glaser and Huisgen 1,3-dipolar cycloaddition reactions. Chem. Asian J. 2013;8:2822–2827. doi: 10.1002/asia.201300690. PubMed DOI

Barot N., Patel S.B., Kaur H. Nitro resin supported copper nanoparticles: An effective heterogeneous catalyst for C–N cross coupling and oxidative C–C homocoupling. J. Mol. Catal. A Chem. 2016;423:77–84. doi: 10.1016/j.molcata.2016.06.009. DOI

Kodicherla B., Perumgani P.C., Mandapati M.R. A reusable polystyrene-supported copper(II) catalytic system for N-arylation of indoles and Sonogashira coupling reactions in water. Appl. Catal. A Gen. 2014;483:110–115. doi: 10.1016/j.apcata.2014.07.001. DOI

Doyle M.P., McKervey M.A., Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides. Wiley-VCH; Weinheim, Germany: 1998. Catalysts for Metal Carbene Transformations.

Mandoli A., Orlandi S., Pini D., Salvadori P. A reusable, insoluble polymer-bound bis(oxazoline) (IPB-box) for highly enantioselective heterogeneous cyclopropanation reactions. Chem. Commun. 2003:2466–2467. doi: 10.1039/b306483b. PubMed DOI

Mandoli A., Garzelli R., Orlandi S., Pini D., Lessi M., Salvadori P. Some factors affecting the catalytic efficiency in the enantioselective cyclopropanation of olefins by the use of insoluble polystyrene-bound bisoxazoline-copper(I) complex. Catal. Today. 2009;140:51–57. doi: 10.1016/j.cattod.2008.07.007. DOI

Burguete M.I., Fraile J.M., García J.I., García-Verdugo E., Herrerías C.I., Luis S.V., Mayoral J.A. Bis(oxazoline)copper complexes covalently bonded to insoluble support as catalysts in cyclopropanation reactions. J. Org. Chem. 2001;66:8893–8901. doi: 10.1021/jo0159338. PubMed DOI

Knight J., Belcher P.E. 2-Aryl-5,5-bisoxazolin-2-yl[1,3]dioxanes as solution phase and immobilised ligands for highly enantioselective cyclopropanations. Tetrahedron Asymmetry. 2005;16:1415–1418. doi: 10.1016/j.tetasy.2005.02.026. DOI

Werner H., Herrerías C.I., Glos M., Gissibl A., Fraile J.M., Péres I., Mayoral J.A., Reiser O. Synthesis of polymer bound azabis(oxazoline) ligands and their application in asymmetric cyclopropanations. Adv. Synth. Catal. 2006;348:125–132. doi: 10.1002/adsc.200505197. DOI

Burguete M.I., Fraile J.M., García-Verdugo E., Luis S.V., Martínez-Merino V., Mayoral J.A. Polymer-supported bis(oxazolines) and related systems: Toward new heterogeneous enantioselective catalysts. Ind. Eng. Chem. Res. 2006;44:8580–8587. doi: 10.1021/ie0488288. DOI

Maestre L., Ozkal E., Ayats C., Beltrán A., Díaz-Requejo M.M., Pérez P.J., Pericàs M.A. A fully recyclable heterogenized Cu catalyst for the general carbene transfer reaction in batch and flow. Chem. Sci. 2015;6:1510–1515. doi: 10.1039/C4SC03277B. PubMed DOI PMC

Peshkov V.A., Pereshivko O.P., Van der Eycken E.V. A walk around the A3-coupling. Chem. Soc. Rev. 2012;41:3790–3807. doi: 10.1039/c2cs15356d. PubMed DOI

Wang L., Cai C. Reusable polymer-anchored amino acid copper complex for the synthesis of propargylamines. J. Chem. Res. 2008;32:538–541. doi: 10.3184/030823408X349989. DOI

Islam M., Roy A.S., Islam S.M. Functionalized polystyrene supported copper(I) complex as an effective and reusable catalyst for propargylamines synthesis in aqueous medium. Catal. Lett. 2016;146:1128–1137. doi: 10.1007/s10562-016-1728-3. DOI

Kodicherla B., Perumgani P.C., Mandapati M.R. Polymer-anchored copper(II) complex: An efficient reusable catalyst for the synthesis of propargylamines. Appl. Organometal. Chem. 2014;28:756–759. doi: 10.1002/aoc.3193. DOI

Perumgani P.C., Keesara S., Parvathaneni S., Mandapati M.R. Polystyrene supported N-phenylpiperazine–Cu(II) complex: An efficient and reusable catalyst for KA2-coupling reactions under solvent-free conditions. New J. Chem. 2016;40:5113–5120. doi: 10.1039/C5NJ03272E. DOI

Gommermann N., Knochel P. Practical highly enantioselective synthesis of propargylamines through a copper-catalyzed one-pot three-component condensation reaction. Chem. Eur. J. 2006;12:4380–4392. doi: 10.1002/chem.200501233. PubMed DOI

Nakamura S., Ohara M., Nakamura Y., Shibata N., Toru T. Copper-catalyzed enantioselective three-component synthesis of optically active propargylamines from aldehydes, amines, and aliphatic alkynes. Chem. Eur. J. 2010;16:2360–2362. doi: 10.1002/chem.200903550. PubMed DOI

Naeimi H., Moradian M. Thioether-based copper(I) Schiff base complex as a catalyst for a direct and asymmetric A3-coupling reaction. Tetrahedron Asymmetry. 2014;25:427–434. doi: 10.1016/j.tetasy.2014.02.002. DOI

Drabina P., Funk P., Růžička A., Hanusek J., Sedlák M. Synthesis, copper(II) complexes and catalytic activity of substituted 6-(1,3-oxazolin-2-yl)pyridine-2-carboxylates. Transit. Met. Chem. 2010;35:363–371. doi: 10.1007/s11243-010-9336-3. DOI

Zeng T., Yang L., Hudson R., Song G., Moores A.R., Li C.-J. Fe3O4 Nanoparticle-supported copper(I) pybox catalyst: Magnetically recoverable catalyst for enantioselective direct-addition of terminal alkynes to imines. Org. Lett. 2011;13:442–445. doi: 10.1021/ol102759w. PubMed DOI

Sasai H., Suzuki T., Arai S., Arai T., Shibasaki M. Basic character of rare earth metal alkoxides. Utilization in catalytic C–C bond-forming reactions and catalytic asymmetric nitroaldol reactions. J. Am. Chem. Soc. 1992;114:4418–4420. doi: 10.1021/ja00037a068. DOI

Ananthi N., Velmathi S. Asymmetric Henry reaction catalyzed by transition metal complexes: A short review. Ind. J. Chem. 2013;52:87–108.

Corey E.J., Zhang F. re- and si-Face-selective nitroaldol reactions catalyzed by a rigid chiral quaternary ammonium salt: A highly stereoselective synthesis of the HIV protease inhibitor Amprenavir (Vertex 478) Angew. Chem. Int. Ed. 1999;38:1931–1934. doi: 10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO;2-4. PubMed DOI

Drabina P., Harmand L., Sedlák M. Enantioselective Henry reaction catalyzed by supported transition metal complexes. Curr. Org. Synth. 2014;11:879–888. doi: 10.2174/1570179411666140806005556. DOI

Harmand L., Drabina P., Pejchal V., Husáková L., Sedlák M. Recyclable catalyst for the asymmetric Henry reaction based on functionalized imidazolidine-4-one-copper(II) complexes supported by a polystyrene copolymer. Tetrahedron Lett. 2015;56:6240–6243. doi: 10.1016/j.tetlet.2015.09.112. DOI

Panov I., Drabina P., Padělková Z., Šimůnek P., Sedlák M. Highly enantioselective nitroaldol reactions catalyzed by copper(II) complexes derived from substituted 2-(pyridin-2-yl)imidazolidin-4-one ligands. J. Org. Chem. 2011;76:4787–4793. doi: 10.1021/jo200703j. PubMed DOI

Nováková G., Drabina P., Frumarová B., Sedlák M. Recyclable enantioselective catalysts based on copper(II) complexes of 2-(pyridine-2-yl)imidazolidine-4-thione: Their application in asymmetric Henry reactions. Adv. Synth. Catal. 2016;358:2541–2552. doi: 10.1002/adsc.201600198. DOI

Arai T., Yokoyama N., Yanagisawa A. A library of chiral imidazoline–aminophenol ligands: Discovery of an efficient reaction sphere. Chem. Eur. J. 2008;14:2052–2059. doi: 10.1002/chem.200701439. PubMed DOI

Desyatkin V.G., Anokhin M.V., Rodionov V.O., Beletskaya I.P. Polystyrene-supported Cu(II)-R-Box as recyclable catalyst in asymmetric Friedel–Crafts reaction. Russ. J. Org. Chem. 2016;52:1717–1727. doi: 10.1134/S1070428016120010. DOI

Orlandi S., Mandoli A., Pini D., Salvadori P. An insoluble polymer-bound bis-oxazoline copper(II) complex: A highly efficient heterogeneous catalyst for the enantioselective Mukaiyama aldol reaction. Angew. Chem. Int. Ed. 2001;40:2519–2521. doi: 10.1002/1521-3773(20010702)40:13<2519::AID-ANIE2519>3.0.CO;2-D. PubMed DOI

Fraile J.M., Pérez I., Mayoral J.A. Comparison of immobilized Box and azaBox–Cu(II) complexes as catalysts for enantioselective Mukaiyama aldol reactions. J. Catal. 2007;252:303–311. doi: 10.1016/j.jcat.2007.09.010. DOI

Huisgen R. 1,3-Dipolar Cycloadditions. Proc. Chem. Soc. 1961:357–396.

Tornøe C.W., Christensen C., Medal M. Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002;67:3057–3064. PubMed

Rostovtset V.V., Green L.G., Fokin V.V., Sharpless K.B.A. Stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes. Angew. Chem. Int. Ed. 2002;41:2596–2599. doi: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4. PubMed DOI

Kolb H.C., Finn M.G., Sharpless K.B.A. Click chemistry: Diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 2001;40:2004–2021. doi: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5. PubMed DOI

Girard C., Onen E., Aufort M., Beauviere S., Samson E., Herscovici J. Reusable polymer-supported catalyst for the [3+2] Huisgen cycloaddition in automation protocols. Org. Lett. 2006;8:1689–1692. doi: 10.1021/ol060283l. PubMed DOI

Chassaing S., Bénéteau V., Pale P. When CuAAC Click Chemistry′ goes heterogenous. Catal. Sci. Technol. 2016;6:923–957. doi: 10.1039/C5CY01847A. DOI

Movassagh B., Rezaei N. Polystyrene resin-supported CuI-cryptand 22 complex: A highly efficient and reusable catalyst for three-component synthesis of 1,4-disubstituted 1,2,3-triazoles under aerobic conditions in water. Tetrahedron. 2014;70:8885–8892. doi: 10.1016/j.tet.2014.09.092. DOI

Rezaei N., Movassagh B. Polystyrene resin-supported CuI-cryptand 22 complex: A highly efficient and reusable catalyst for the formation of aryl-sulfur bonds in aqueous media. Tetrahedron Lett. 2016;57:1625–1628. doi: 10.1016/j.tetlet.2016.03.005. DOI

Tavassoli M., Landarani-Isfahani A., Moghadam M., Tangestaninejad S., Valliolah Mirkhani V., Mohammadpoor-Baltork I. Polystyrene-supported ionic liquid copper complex: A reusable catalyst for one-pot three-component click reaction. Appl. Catal. A. 2015;503:186–195. doi: 10.1016/j.apcata.2015.07.015. DOI

Martín-Matute B., Pereira S.I., Peña-Cabrera E., Adrio J., Silva A.M.S., Carretero J.C. Synthesis of polymer-supported Fesulphos ligands and their application in asymmetric catalysis. Adv. Synth. Catal. 2007;349:1714–1724. doi: 10.1002/adsc.200600647. DOI

Maurya M.R., Sikarwar S., Joseph T., Halligudi S.B. Bis(2-[α-hydroxyethyl]benzimidazolato)copper(II) anchored onto chloromethylated polystyrene for the biomimetic oxidative coupling of 2-aminophenol to 2-aminophenoxazine-3-one. J. Mol. Catal. A Chem. 2005;236:132–138. doi: 10.1016/j.molcata.2005.02.034. DOI

Hassan J., Sévignon M., Gozzi C., Schulz E., Lemaire M. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction. Chem. Rev. 2002;102:1359–1470. doi: 10.1021/cr000664r. PubMed DOI

Ullmann F., Jean Bielecki J. Ueber Synthesen in der Biphenylreihe. Chem. Ber. 1901;34:2174–2185. doi: 10.1002/cber.190103402141. DOI

Lan J.-B., Chen L., Yu X.-Q., You J.-S., Xie R.-G. A simple copper salt catalyzed the coupling of imidazole with arylboronic acids in protic solvent. Chem. Commun. 2004:188–189. doi: 10.1039/b307734a. PubMed DOI

Islam S.M., Mondal S., Mondal P., Roy A.S., Tuhina K, Salam N., Mobarak M. A reusable polymer supported copper catalyst for the C–N and C–O bond cross-coupling reaction of aryl halides as well as arylboronic acids. J. Organomet. Chem. 2012;696:4264–4274. doi: 10.1016/j.jorganchem.2011.10.004. DOI

Islam S.M., Mondal S., Mondal P., Roy A.S., Tuhina K., Salam N., Sumantra P., Hossain D., Mobarok M. An efficient polymer-supported copper(II) catalyst for the N-arylation reaction of N(H)-heterocycles with aryl halides as well as arylboronic acids. Transit. Met. Chem. 2011;36:447–458. doi: 10.1007/s11243-011-9489-8. DOI

Islam M., Salam N., Mondal P., Roy A.S., Ghosh K., Tuhina K. A highly active reusable polymer anchored copper catalyst for C–O, C–N and C–S cross coupling reactions. J. Mol. Catal. A Chem. 2014;387:7–19. doi: 10.1016/j.molcata.2014.02.007. DOI

Nasrollahzadeh M., Zahraei A., Pourbasheer E. Catalytic activity and antibacterial properties of nanopolymer-supported copper complex for C–N coupling reactions of amines and nitrogen-containing heterocycles with aryl halides. Monatsh. Chem. 2015;146:1329–1334. doi: 10.1007/s00706-014-1367-6. DOI

Islam M.M., Halder H., Roy A.S., Chatterjee S., Bhaumik A., Islam S.M. Copper(II) incorporated functionalized polystyrene catalyzed N-arylation of amides under solvent free condition with broad substrate scope. RSC Adv. 2016;6:109692–109701. doi: 10.1039/C6RA24459A. DOI

Huang L., Yu R., Zhu X., Wan Y. A recyclable Cu-catalyzed C–N coupling reaction in water and its application to synthesis of imidazo[1,2-a]quinoxaline. Tetrahedron. 2013;69:8974–8977. doi: 10.1016/j.tet.2013.07.036. DOI

Cardillo G., Tomasini C. Asymmetric synthesis of β-amino acids and α-substituted β-amino acids. Chem. Soc. Rev. 1996;25:117–128. doi: 10.1039/CS9962500117. DOI

Li L., Liu Z., Ling Q., Xing X. Polystyrene-supported CuI–imidazole complex catalyst for aza-Michael reaction of imidazoles with α,β-unsaturated compounds. J. Mol. Catal. A Chem. 2012;353:178–184. doi: 10.1016/j.molcata.2011.11.023. DOI

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