Generic placeholder image

Current Chinese Chemistry

Editor-in-Chief

ISSN (Print): 2666-0016
ISSN (Online): 2666-0008

Mini-Review Article

Recent Advances of Calcium Carbide in Organic Reactions

Author(s): Fan-Lin Zeng, Qi-Yan Lv, Xiao-Lan Chen* and Bing Yu*

Volume 1, Issue 1, 2021

Published on: 17 August, 2020

Page: [3 - 10] Pages: 8

DOI: 10.2174/2666001601999200817111836

Abstract

Calcium carbide (CaC2) as an important raw material has been widely used in inorganic chemistry, nanomaterials, supramolecular and other fields. In recent years, calcium carbide has been applied as an inexpensive, safe, green, and sustainable acetylene source in organic synthesis. This mini-review summarizes the latest progress of calcium carbide as a surrogate of acetylene gas in organic reactions for the construction of C-C, C-N, C-S, and C-O bonds.

Keywords: Calcium carbide, organic reaction, acetylene, sustainable, palladium, copper.

Graphical Abstract

[1]
Hamberger, M.; Liebig, S.; Friedrich, U.; Korber, N.; Ruschewitz, U. Evidence of solubility of the acetylide ion C22−: syntheses and crystal structures of K2C22NH3, Rb2C22NH3, and Cs2C27NH3. Angew. Chem. Int. Ed., 2012, 51, 13006-13010.
[http://dx.doi.org/10.1002/anie.201206349] [PMID: 23161511]
[2]
Tedeschi, R.J. Acetylene-based chemicals from coal and other natural resources., 1982. United States.
[3]
Rodygin, K.S.; Vikenteva, Y.A.; Ananikov, V.P. Calcium-based sustainable chemical technologies for total carbon recycling. ChemSusChem, 2019, 12, 1483-1516.
[http://dx.doi.org/10.1002/cssc.201802412] [PMID: 30938099]
[4]
Trotuş, I-T.; Zimmermann, T.; Schüth, F. Catalytic reactions of acetylene: a feedstock for the chemical industry revisited. Chem. Rev., 2014, 114, 1761-1782.
[http://dx.doi.org/10.1021/cr400357r] [PMID: 24228942]
[5]
Rodygin, K.S.; Werner, G.; Kucherov, F.A.; Ananikov, V.P. Calcium carbide: a unique reagent for organic synthesis and nanotechnology. Chem. Asian J., 2016, 11, 965-976.
[http://dx.doi.org/10.1002/asia.201501323] [PMID: 26898248]
[6]
Fu, R.; Li, Z.; Gao, L. Direct synthesis of organic compounds using calcium carbide as the acetylene source. Prog. Chem., 2019, 31, 1303-1313.
[7]
Voronin, V.V.; Ledovskaya, M.S.; Bogachenkov, A.S.; Rodygin, K.S.; Ananikov, V.P. Acetylene in organic synthesis: recent progress and new uses. Molecules, 2018, 23, 2442.
[http://dx.doi.org/10.3390/molecules23102442] [PMID: 30250005]
[8]
Zhang, W.; Wu, H.; Liu, Z.; Zhong, P.; Zhang, L.; Huang, X.; Cheng, J. The use of calcium carbide in one-pot synthesis of symmetric diaryl ethynes. Chem. Commun., 2006, 46, 4826-4828.
[http://dx.doi.org/10.1039/b607809e] [PMID: 17345742]
[9]
Chuentragool, P.; Vongnam, K.; Rashatasakhon, P.; Sukwattanasinitt, M.; Wacharasindhu, S. Calcium carbide as a cost-effective starting material for symmetrical diarylethynes via Pd-catalyzed coupling reaction. Tetrahedron, 2011, 67, 8177-8182.
[http://dx.doi.org/10.1016/j.tet.2011.08.042]
[10]
Hosseini, A.; Pilevar, A.; Hogan, E.; Mogwitz, B.; Schulze, A.S.; Schreiner, P.R. Calcium carbide catalytically activated with tetra-n-butyl ammonium fluoride for Sonogashira cross coupling reactions. Org. Biomol. Chem., 2017, 15, 6800-6807.
[http://dx.doi.org/10.1039/C7OB01334E] [PMID: 28770930]
[11]
Fu, R.; Li, Z. Direct synthesis of symmetric diarylethynes from calcium carbide and arylboronic acids/esters. Eur. J. Org. Chem., 2017, 2017, 6648-6651.
[http://dx.doi.org/10.1002/ejoc.201701234]
[12]
Geyang, S.; Zheng, L. One-pot multi-component synthesis of triarylacrylonitriles directly by using CaC2 as a concise acetylene source and K4[Fe(CN)6] as an eco-friendly cyanide source. Eur. J. Org. Chem., 2018, 2018, 1326-1332.
[http://dx.doi.org/10.1002/ejoc.201701711]
[13]
Lu, H.; Li, Z. Palladium-catalyzed one-pot four-component synthesis of α-Cyano-α,β-unsaturated ketones using calcium carbide as an acetylene source and potassium hexacyanoferrate(II) as an eco-friendly cyanide source. Adv. Synth. Catal., 2019, 361, 4474-4482.
[http://dx.doi.org/10.1002/adsc.201900733]
[14]
Lin, Z.; Yu, D.; Sum, Y.N.; Zhang, Y. Synthesis of functional acetylene derivatives from calcium carbide. ChemSusChem, 2012, 5, 625-628.
[http://dx.doi.org/10.1002/cssc.201100649] [PMID: 22378645]
[15]
Yu, D.; Sum, Y.N.; Ean, A.C.C.; Chin, M.P.; Zhang, Y. Acetylide ion (C22−) as a synthon to link electrophiles and nucleophiles: a simple method for enaminone synthesis. Angew. Chem. Int. Ed., 2013, 52, 5125-5128.
[http://dx.doi.org/10.1002/anie.201301019] [PMID: 23576293]
[16]
Teong, S.P.; Yu, D.; Sum, Y.N.; Zhang, Y. Copper catalysed alkynylation of tertiary amines with CaC2 via sp3 C-H activation. Green Chem., 2016, 18, 3499-3502.
[http://dx.doi.org/10.1039/C6GC00872K]
[17]
Gao, L.; Li, Z. Direct synthesis of 1-Arylprop-1-ynes with calcium carbide as an acetylene source. Synlett, 2019, 30, 1580-1584.
[http://dx.doi.org/10.1055/s-0037-1610718]
[18]
Gao, L.; Li, Z. Synthesis of aromatic terminal allenes and aliphatic terminal alkynes from hydrazones using calcium carbide as an acetylene source. Org. Chem. Front., 2020, 7, 702-708.
[http://dx.doi.org/10.1039/C9QO01400D]
[19]
Coats, S.J.; Link, J.S.; Gauthier, D.; Hlasta, D.J. Trimethylsilyl-directed 1,3-dipolar cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles. Org. Lett., 2005, 7, 1469-1472.
[http://dx.doi.org/10.1021/ol047637y] [PMID: 15816729]
[20]
Wu, L.-Y.; Xie, Y.-X.; Chen, Z.-S.; Niu, Y.-N.; Liang, Y.-M. A convenient synthesis of 1-substituted 1,2,3-triazoles via CuI/Et3N catalyzed ‘Click Chemistry’ from azides and acetylene gas. Synlett, 2009, 2009, 1453-1456.
[http://dx.doi.org/10.1055/s-0029-1216745]
[21]
Jiang, Y.; Kuang, C.; Yang, Q. The use of calcium carbide in the synthesis of 1-monosubstituted aryl 1,2,3-triazole via click chemistry. Synlett, 2009, 2009, 3163-3166.
[http://dx.doi.org/10.1055/s-0029-1218346]
[22]
Gonda, Z.; Lőrincz, K.; Novák, Z. Efficient synthesis of deuterated 1,2,3-triazoles. Tetrahedron Lett., 2010, 51, 6275-6277.
[http://dx.doi.org/10.1016/j.tetlet.2010.09.097]
[23]
Yang, Q.; Jiang, Y.; Kuang, C. Facile one-pot synthesis of monosubstituted 1-Aryl-1H-1,2,3-triazoles from Arylboronic Acids and Prop-2-ynoic Acid (= Propiolic Acid) or Calcium Acetylide (= Calcium Carbide) as acetylene source. Helv. Chim. Acta, 2012, 95, 448-454.
[http://dx.doi.org/10.1002/hlca.201100256]
[24]
Lu, H.; Li, Z. Synthesis of 1,2,3-triazolyl-based ketoximes using calcium carbide as an acetylene source. Eur. J. Org. Chem., 2020, 2020, 845-851.
[http://dx.doi.org/10.1002/ejoc.201901712]
[25]
Fu, R.; Li, Z. Direct synthesis of 2-Methylbenzofurans from calcium carbide and salicylaldehyde p-Tosylhydrazones. Org. Lett., 2018, 20, 2342-2345.
[http://dx.doi.org/10.1021/acs.orglett.8b00676] [PMID: 29633847]
[26]
Hosseini, A.; Schreiner, P.R. Synthesis of exclusively 4-substituted β-Lactams through the kinugasa reaction utilizing calcium carbide. Org. Lett., 2019, 21, 3746-3749.
[http://dx.doi.org/10.1021/acs.orglett.9b01192] [PMID: 31059273]
[27]
Sum, Y.N.; Yu, D.; Zhang, Y. Synthesis of acetylenic alcohols with calcium carbide as the acetylene source. Green Chem., 2013, 15, 2718-2721.
[http://dx.doi.org/10.1039/c3gc41269e]
[28]
Li, Z.; He, L.; Fu, R.; Song, G.; Song, W.; Xie, D.; Yang, J. One-step construction of saturated six-membered rings directly using calcium carbide as an acetylene source: synthesis of 1,3,5-triaroylcyclohexanes. Tetrahedron, 2016, 72, 4321-4328.
[http://dx.doi.org/10.1016/j.tet.2016.05.071]
[29]
Kaewchangwat, N.; Sukato, R.; Vchirawongkwin, V.; Vilaivan, T.; Sukwattanasinitt, M.; Wacharasindhu, S. Direct synthesis of aryl substituted pyrroles from calcium carbide: an underestimated chemical feedstock. Green Chem., 2015, 17, 460-465.
[http://dx.doi.org/10.1039/C4GC01615G]
[30]
Yu, Y.; Huang, W.; Chen, Y.; Gao, B.; Wu, W.; Jiang, H. Calcium carbide as the acetylide source: transition-metal-free synthesis of substituted pyrazoles via [1,5]-sigmatropic rearrangements. Green Chem., 2016, 18, 6445-6449.
[http://dx.doi.org/10.1039/C6GC02776H]
[31]
Yu, Y.; Chen, Y.; Huang, W.; Wu, W.; Jiang, H. One-pot synthesis of spirocyclic or fused pyrazoles from cyclic ketones: calcium carbide as the carbon source in ring expansion. J. Org. Chem., 2017, 82, 9479-9486.
[http://dx.doi.org/10.1021/acs.joc.7b01496] [PMID: 28831796]
[32]
Rodygin, K.S.; Ananikov, V.P. An efficient metal-free pathway to vinyl thioesters with calcium carbide as the acetylene source. Green Chem., 2016, 18, 482-486.
[http://dx.doi.org/10.1039/C5GC01552A]
[33]
Rattanangkool, E.; Vilaivan, T.; Sukwattanasinitt, M.; Wacharasindhu, S. An atom-economic approach for vinylation of indoles and phenols using calcium carbide as acetylene surrogate. Eur. J. Org. Chem., 2016, 2016, 4347-4353.
[http://dx.doi.org/10.1002/ejoc.201600666]
[34]
Matake, R.; Adachi, Y.; Matsubara, H. Synthesis of vinyl ethers of alcohols using calcium carbide under superbasic catalytic conditions (KOH/DMSO). Green Chem., 2016, 18, 2614-2618.
[http://dx.doi.org/10.1039/C5GC02977E]
[35]
Teong, S.P.; Chua, A.Y.H.; Deng, S.; Li, X.; Zhang, Y. Direct vinylation of natural alcohols and derivatives with calcium carbide. Green Chem., 2017, 19, 1659-1662.
[http://dx.doi.org/10.1039/C6GC03579E]
[36]
Teong, S.P.; Lim, J.; Zhang, Y. Vinylation of aryl ether (Lignin β-O-4 Linkage) and epoxides with calcium carbide through C−O bond cleavage. ChemSusChem, 2017, 10, 3198-3201.
[http://dx.doi.org/10.1002/cssc.201701153] [PMID: 28730737]
[37]
Ledovskaya, M.S.; Voronin, V.V.; Rodygin, K.S.; Posvyatenko, A.V.; Egorova, K.S.; Ananikov, V.P. Direct synthesis of deuterium-labeled O-, S-, N-vinyl derivatives from calcium carbide. Synthesis, 2019, 51, 3001-3013.
[http://dx.doi.org/10.1055/s-0037-1611518]
[38]
Hosseini, A.; Seidel, D.; Miska, A.; Schreiner, P.R. Fluoride-assisted activation of calcium carbide: a simple method for the ethynylation of aldehydes and ketones. Org. Lett., 2015, 17, 2808-2811.
[http://dx.doi.org/10.1021/acs.orglett.5b01219] [PMID: 25997788]
[39]
Samzadeh-Kermani, A. Ethynylation of isoquinoline and quinoline derivatives with calcium carbide. Synlett, 2017, 28, 2126-2130.
[http://dx.doi.org/10.1055/s-0036-1590815]
[40]
Ledovskaya, M.S.; Rodygin, K.S.; Ananikov, V.P. Calcium-mediated one-pot preparation of isoxazoles with deuterium incorporation. Org. Chem. Front., 2018, 5, 226-231.
[http://dx.doi.org/10.1039/C7QO00705A]

© 2024 Bentham Science Publishers | Privacy Policy