Application of Nanocatalysts in C-Te Cross-Coupling Reactions: An Overview

Document Type: Review Article

Authors

1 Payame Noor University

2 University of Tehran

Abstract

Synthesis of organo-telluride compounds through nanoparticles catalyzed C-Te cross-coupling reactions has drawn considerable attention in the past several years. This mini review is an attempt to highlight the most important advances and contributions in this fast-growing research field with the emphasis on the mechanistic aspects of the reactions. The reactions are classified based on the type (e.g. coupling of organic halides with elemental Te(0), coupling of terminal acetylenes with ditellurides). Literature has been surveyed from 2009 to end of 2018

Graphical Abstract

Application of Nanocatalysts in C-Te Cross-Coupling Reactions: An Overview

Keywords


[1] a) S. Sarhandi, M. Daghagheleh, M. Vali, R. Moghadami, E. Vessally, New insight in Hiyama cross-coupling reactions: Decarboxylative, denitrogenative and desulfidative couplings: A review, Chem. Rev. Lett. 1 (2018) 9-15; b) M. Daghagheleh, M. Vali, Z. Rahmani, S. Sarhandi, E. Vessally, A review on the CO2 incorporation reactions using arynes, Chem. Rev. Lett. 1 (2018) 23-30.

[2] a) M. Fañanás-Mastral, Copper-catalyzed arylation with diaryliodonium salts, Synthesis, 49 (2017) 1905-1930.

[3] F.-S. Han, Transition-metal-catalyzed Suzuki–Miyaura cross-coupling reactions: a remarkable advance from palladium to nickel catalysts, Chem. Soc. Rev., 42 (2013) 5270-5298; b) C.C. Johansson Seechurn, M.O. Kitching, T.J. Colacot, V. Snieckus, Palladium‐catalyzed cross‐coupling: a historical contextual perspective to the 2010 Nobel Prize, Angew. Chem. Int. Ed., 51 (2012) 5062-5085.

[4] I.P. Beletskaya, V.P. Ananikov, Transition-metal-catalyzed C−S, C−Se, and C−Te bond formation via cross-coupling and atom-economic addition reactions, Chem. Rev., 111 (2011) 1596-1636.

[5] M.-L. Louillat, F.W. Patureau, Oxidative C–H amination reactions, Chem. Soc. Rev., 43 (2014) 901-910.

[6] X. Zhu, S. Chiba, Copper-catalyzed oxidative carbon–heteroatom bond formation: a recent update, Chem. Soc. Rev., 45 (2016) 4504-4523.

[7] Y. Nishibayashi, C.S. Cho, S. Uemura, Palladium-catalyzed cross-coupling reactions between organic tellurides and alkenes, J. Organomet. Chem., 507 (1996) 197-200.

[8] M. Palomba, L. Bagnoli, F. Marini, C. Santi, L. Sancineto, Recent advances in the chemistry of vinylchalcogenides, Phosphorus Sulfur Silicon Relat Elem., 191 (2016) 235-244.

[9] S. Koguchi, Y. Shibuya, Y. Igarashi, H. Takemura, C–Te cross-coupling of diaryl ditellurides with arylboronic acids by using copper (I) thiophene-2-carboxylate under mild conditions, Synlett, (2018).

[10] N. Budisa, W. Karnbrock, S. Steinbacher, A. Humm, L. Prade, T. Neuefeind, L. Moroder, R. Huber, Bioincorporation of telluromethionine into proteins: a promising new approach for X-ray structure analysis of proteins1, J. Mol. Biol., 270 (1997) 616-623.

[11] J.L. Princival, A.A.D. Santos, J.V. Comasseto, Reactive organometallics from organotellurides: application in organic synthesis, J. Brazil, Chem. Soc., 21 (2010) 2042-2054.

[12] V. Polshettiwar, R.S. Varma, Green chemistry by nano-catalysis, Green Chem., 12 (2010) 743-754.

[13] A. Fihri, M. Bouhrara, B. Nekoueishahraki, J.-M. Basset, V. Polshettiwar, Nanocatalysts for Suzuki cross-coupling reactions, Chem. Soc. Rev., 40 (2011) 5181-5203.

[14] T. Cheng, D. Zhang, H. Li, G. Liu, Magnetically recoverable nanoparticles as efficient catalysts for organic transformations in aqueous medium, Green Chem., 16 (2014) 3401-3427.

[15] a) E. Vessally, H. Saeidian, A. Hosseinian, L. Edjlali, A. Bekhradnia, A review on synthetic applications of oxime esters, Curr.Org. Chem., 21 (2017) 249-271; b) E. Vessally, L. Edjlali, A. Hosseinian, A. Bekhradnia, M.D. Esrafili, Novel routes to quinoline derivatives from N-propargylamines, RSC Adv., 6 (2016) 49730-49746; c) E. Vessally, A. Hosseinian, L. Edjlali, A. Bekhradnia, M.D. Esrafili, New page to access pyridine derivatives: synthesis from N-propargylamines, RSC Adv., 6 (2016) 71662-71675; d) E. Vessally, A. Hosseinian, L. Edjlali, A. Bekhradnia, M. D Esrafili, New page to access pyrazines and their ring fused analogues: Synthesis from N-propargylamines, Curr.Org. Synth., 14 (2017) 557-567; e) E. Vessally, A. Hosseinian, L. Edjlali, A. Bekhradnia, M.D. Esrafili, New route to 1, 4-oxazepane and 1, 4-diazepane derivatives: synthesis from N-propargylamines, RSC Adv., 6 (2016) 99781-99793; f) E. Vessally, S. Soleimani-Amiri, A. Hosseinian, L. Edjlali, A. Bekhradnia, New protocols to access imidazoles and their ring fused analogues: synthesis from N-propargylamines, RSC Adv., 7 (2017) 7079-7091; g) M. Babazadeh, S. Soleimani-Amiri, E. Vessally, A. Hosseinian, L. Edjlali, Transition metal-catalyzed [2+2+2] cycloaddition of nitrogen-linked 1, 6-diynes: a straightforward route to fused pyrrolidine systems, RSC Adv., 7 (2017) 43716-43736; g) E. Vessally, A. Hosseinian, L. Edjlali, E. Ghorbani-Kalhor, R. Hosseinzadeh-Khanmiri, Intramolecular cyclization of N-propargyl anilines: a new synthetic entry into highly substituted indoles, J. Iran. Chem. Soc., 14 (2017) 2339-2353; h) E. Vessally, A. Hosseinian, L. Edjlali, M. Babazadeh, R. Hosseinzadeh-Khanmiri, New strategy for the synthesis of morpholine cores: synthesis from N-propargylamines, Iran. J. Chem. Chem. Eng., 36 (2017) 1-13; i) S. Arshadi, E. Vessally, M. Sobati, A. Hosseinian, A. Bekhradnia, Chemical fixation of CO2 to N-propargylamines: a straightforward route to 2-oxazolidinones, J. CO2 Util., 19 (2017) 120-129; j) E. Vessally, M. Babazadeh, K. Didehban, A. Hosseinian, L. Edjlali, Intramolecular ipso-Cyclization of N-Arylpropiolamides: A Novel and Straightforward Synthetic Approach for Azaspiro [4.5] decatrien-2-ones, Curr. Org. Chem., 22 (2018) 286-297; k) E. Vessally, M. Babazadeh, K. Didehban, A. Hosseinian, L. Edjlali, Intramolecular Cyclization of N-Arylpropiolamides: A New Strategy for the Synthesis of Functionalized 2-Quinolones, Curr. Org. Chem., 21 (2017) 2561-2572; l) S. Shahidi, P. Farajzadeh, P. Ojaghloo, A. Karbakhshzadeh, A. Hosseinian, Nanocatalysts for conversion of aldehydes/alcohols/amines to nitriles: A review, Chem. Rev. Lett. 1 (2018) 37-44.

[16] a) S. Soleimani-Amiri, E. Vessally, M. Babazadeh, A. Hosseinian, L. Edjlali, Intramolecular cyclization of N-allyl propiolamides: a facile synthetic route to highly substituted γ-lactams (a review), RSC Adv., 7 (2017) 28407-28418; b) E. Vessally, M. Babazadeh, A. Hosseinian, L. Edjlali, L. Sreerama, Recent Advances in Synthesis of Functionalized β-Lactams through Cyclization of N-Propargyl Amine/Amide Derivatives, Curr. Org. Chem., 22 (2018) 199-205; c) E. Vessally, A. Hosseinian, M. Babazadeh, L. Edjlali, R. Hosseinzadeh-Khanmiri, Metal Catalyzed Carboxylative Coupling of Terminal Alkynes, Organohalides and Carbon Dioxide: A Novel and Promising Synthetic Strategy toward 2-Alkynoates (A Review), Curr. Org. Chem., 22 (2018) 315-322; d) E. Vessally, M. Nikpasand, S. Ahmadi, P.D.K. Nezhad, A. Hosseinian, Transition metal-catalyzed intramolecular cyclization of N-Boc-protected propargyl/ethynyl amines: a novel and convenient access to 2-oxazolidinone/oxazolone derivatives, J. Iran. Chem. Soc., (2018) DOI: 10.1007/s13738-018-1542-5; e) S. Arshadi, E. Vessally, A. Hosseinian, S. Soleimani-amiri, L. Edjlali, Three-component coupling of CO2, propargyl alcohols, and amines: An environmentally benign access to cyclic and acyclic carbamates (A Review), J. CO2 Util., 21 (2017) 108-118; f) E. Vessally, S. Soleimani-Amiri, A. Hosseinian, L. Edjlali, M. Babazadeh, Chemical fixation of CO2 to 2-aminobenzonitriles: a straightforward route to quinazoline-2, 4 (1H, 3H)-diones with green and sustainable chemistry perspectives, J. CO2 Util., 21 (2017) 342-352; g) E. Vessally, M. Babazadeh, A. Hosseinian, S. Arshadi, L. Edjlali, Nanocatalysts for chemical transformation of carbon dioxide, J. CO2 Util., 21 (2017) 491-502; h) E. Vessally, K. Didehban, M. Babazadeh, A. Hosseinian, L. Edjlali, Chemical fixation of CO2 with aniline derivatives: A new avenue to the synthesis of functionalized azole compounds (A review), J. CO2 Util., 21 (2017) 480-490; i) E. Vessally, A. Hosseinian, L. Edjlali, M. Babazadeh, K. Didehban, Chemical Fixation of CO2 to Allylic (α-Allenylic) Amines: A Green Route to Synthesis of Functionalized 2-Oxazolidones, Mini-Rev. Org. Chem., 15 (2018) 315-323; j) A. Hosseinian, M. Babazadeh, L. Edjlali, Z. Rahmani, E. Vessally, Intramolecular Cyclization of Aryl Propargyl Ethers: A Straightforward and Convenient Approach to Benzofuran Derivatives, Curr. Org. Synth., 15 (2018) 972-981; k) E. Vessally, R. Mohammadi, A. Hosseinian, L. Edjlali, M. Babazadeh, Three component coupling of amines, alkyl halides and carbon dioxide: An environmentally benign access to carbamate esters (urethanes), J. CO2 Util., 24 (2018) 361-368; l) E. Vessally, K. Didehban, R. Mohammadi, A. Hosseinian, M. Babazadeh, Recent advantages in the metal (bulk and nano)-catalyzed S-arylation reactions of thiols with aryl halides in water: a perfect synergy for eco-compatible preparation of aromatic thioethers, J. Sulfur Chem., 39 (2018) 332-349; m) K. Didehban, E. Vessally, A. Hosseinian, L. Edjlali, E.S. Khosroshahi, Nanocatalysts for C–Se cross-coupling reactions, RSC Adv., 8 (2018) 291-301; n) E. Vessally, R. Mohammadi, A. Hosseinian, K. Didehban, L. Edjlali, S-arylation of 2-mercaptobenzazoles: a comprehensive review, J. Sulfur Chem., 39 (2018) 443-463; o) A. Hosseinian, S. Farshbaf, R. Mohammadi, A. Monfared, E. Vessally, Advancements in six-membered cyclic carbonate (1, 3-dioxan-2-one) synthesis utilizing carbon dioxide as a C1 source, RSC Adv., 8 (2018) 17976-17988; p) A. Hosseinian, S. Farshbaf, L.Z. Fekri, M. Nikpassand, E. Vessally, Cross-Dehydrogenative Coupling Reactions Between P (O)–H and X–H (X= S, N, O, P) Bonds, Top. Curr. Chem., 376 (2018) 23; q) F.A.H. Nasab, L.Z. Fekri, A. Monfared, A. Hosseinian, E. Vessally, Recent advances in sulfur–nitrogen bond formation via cross-dehydrogenative coupling reactions, RSC Adv., 8 (2018) 18456-18469; r) A. Hosseinian, S. Ahmadi, A. Monfared, P.D. Nezhad, E. Vessally, Nano-structured Catalytic Systems in Cyanation of Aryl Halides with K4 [Fe (CN) 4], Curr. Org. Chem., 22 (2018) 1862-1874; s) A. Hosseinian, L. Zare Fekri, A. Monfared, E. Vessally, M. Nikpassand, Transition-metal-catalyzed C–N cross-coupling reactions of N-unsubstituted sulfoximines: a review, J. Sulfur Chem., 39 (2018) 674-698; t) A. Hosseinian, S. Ahmadi, F.A.H. Nasab, R. Mohammadi, E. Vessally, Cross-Dehydrogenative C–H/S–H Coupling Reactions, Top. Curr. Chem., 376 (2018) 39; u) A. Hosseinian, F.A.H. Nasab, S. Ahmadi, Z. Rahmani, E. Vessally, Decarboxylative cross-coupling reactions for P (O)–C bond formation, RSC Adv., 8 (2018) 26383-26398.

 [17] D. Singh, A.M. Deobald, L.R. Camargo, G. Tabarelli, O.E. Rodrigues, A.L. Braga, An efficient one-pot synthesis of symmetrical diselenides or ditellurides from halides with CuO nanopowder/Se0 or Te0/base, Org. Lett., 12 (2010) 3288-3291.

[18] G.V. Botteselle, M. Godoi, F.Z. Galetto, L. Bettanin, D. Singh, O.E. Rodrigues, A.L. Braga, Microwave-assisted one-pot synthesis of symmetrical diselenides, ditellurides and disulfides from organoyl iodides and elemental chalcogen catalyzed by CuO nanoparticles, J. Mol. Catal., 365 (2012) 186-193.

[19] M.Z. Kassaee, E. Motamedi, B. Movassagh, S. Poursadeghi, Iron-catalyzed formation of C–Se and C–Te bonds through cross coupling of aryl halides with Se(0) and Te(0)/nano-Fe3O4@GO, Synthesis, 45 (2013) 2337-2342.

[20] M. Godoi, E.W. Ricardo, T.E. Frizon, M.S. Rocha, D. Singh, M.W. Paixao, A.L. Braga, An efficient synthesis of alkynyl selenides and tellurides from terminal acetylenes and diorganyl diselenides or ditellurides catalyzed by recyclable copper oxide nanopowder, Tetrahedron, 68 (2012) 10426-10430.

[21] M. Godoi, D.G. Liz, E.W. Ricardo, M.S. Rocha, J.B. Azeredo, A.L. Braga, Magnetite (Fe3O4) nanoparticles: an efficient and recoverable catalyst for the synthesis of alkynyl chalcogenides (selenides and tellurides) from terminal acetylenes and diorganyl dichalcogenides, Tetrahedron, 70 (2014) 3349-3354.

[22] D. Alves, C.G. Santos, M.W. Paixão, L.C. Soares, D. de Souza, O.E. Rodrigues, A.L. Braga, CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids, Tetrahedron Lett., 50 (2009) 6635-6638.

[23] D. Kundu, N. Mukherjee, B.C. Ranu, 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., 3 (2013) 117-125.

[24] B. Mohan, C. Yoon, S. Jang, K.H. Park, Copper nanoparticles catalyzed Se(Te)-Se(Te) bond activation: A straightforward route towards unsymmetrical organochalcogenides from boronic acids, ChemCatChem, 7 (2015) 405-412.

[25] S. Roy, T. Chatterjee, S.M. Islam, Solvent selective phenyl selenylation and phenyl tellurylation of aryl boronic acids catalyzed by Cu (II) grafted functionalized polystyrene, Tetrahedron Lett., 56 (2015) 779-783.