Abstract
A facile, efficient and general synthesis of a broad range of structurally variant alkoxymethylphosphonium tetrafluoroborates (2a–e) is described. The reaction involves the triphenylphosphination of bis-alkoxy methanes in the presence of ethereal boron trifluoride at room temperature. Application of these new salts to carbon homologation of aldehydes is also studied.
Graphical abstract
Similar content being viewed by others
References
Maryanoff BE, Reitz AB (1989) The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects. Chem Rev 89(4):863–927
Effenberger F, Meller P, Ringsdorf H, Schlosser H (1991) Properties of amphiphilic terminally substituted conjugated nonaene-and 2-docosylnonaene carboxylic acids in monolayers at the air-water interface. Adv Mater 3(11):555–558
Kolodiazhnyi OI (1996) C-element-substituted phosphorus yelids. Tetrahedron 52(6):1855–1929
Hwang LK, Na Y, Lee J, Do Y, Chang S (2005) Tetraarylphosphonium halides as arylating reagents in Pd-catalyzed heck and cross-coupling reactions. Angew Chem Int Ed 44(38):6166–6169
Deng Z, Lin JH, Xiao JC (2016) Nucleophilic arylation with tetraarylphosphonium salts. Nat Commun 7:10337
Szymczyk M (2017) Unexpected course of Wittig reaction when using cinnamyl aldehyde as a substrate. Phosphorus Sulfur Silicon Relat Elem 192(3):264–266
Roy MN, Poupon JC, Charette AB (2009) Tetraarylphosphonium salts as soluble supports for oxidative catalysts and reagents. J Org Chem 74(22):8510–8515
Cao H, McNamee L, Alper H (2008) Palladium-catalyzed thiocarbonylation of iodoarenes with thiols in phosphonium salt ionic liquids. J Org Chem 73(9):3530–3534
Winkel A, Reddy PVG, Wilhelm R (2008) Recent advances in the synthesis and application of chiral ionic liquids. Synthesis 07:999–1016
McNulty J, Cheekoori S, Bender TP, Coggan JA (2007) A pronounced anionic effect in the Pd-catalyzed Buchwald–Hartwig amination reaction revealed in phosphonium salt ionic liquids. Eur J Org Chem 9:1423–1428
Zurawinski R, Donnadieu B, Mikolajczyk M, Chauvin R (2004) Palladium complexes of a chiral P, C-chelating phosphino-(sulfinylmethyl) phosphonium ylide ligand. J Organomet Chem 689(2):380–386
Ohta T, Sasayama H, Nakajima O, Kurahashi N, Fujii T, Furukawa I (2003) Asymmetric allylic substitution catalyzed by palladium—Yliphos complex. Tetrahedron Asymmetry 14(5):537–542
Leglaye P, Donnadieu B, Brunet JJ, Chauvin R (1998) Methyldiopium and methylbinapium, chiral phosphonium-phosphine ligands. Tetrahedron Lett 39(50):9179–9182
Laleu B, Bernardinelli G, Chauvin R, Lacour J (2006) Trimesitylmethylphosphonium cation. Supramolecular stereocontrol and simple enantiomerization mechanism determination. J Org Chem 71(19):7412–7416
Hamdi A, Nam KC, Ryu BJ, Kim JS, Vicens J (2004) Anion complexation. A ditriphenylphosphonium calix[4]arene derivative as a novel receptor for anions. Tetrahedron Lett 45(24):4689–4692
Shahbaz K, Mjalli FS, Hashim MA, AlNashef IM (2011) Using deep eutectic solvents based on methyltriphenyl phosphunium bromide for the removal of glycerol from palm-oil-based biodiesel. Energy Fuels 25(6):2671–2678
Kareem MA, Mjalli FS, Hashim MA, AlNashef IM (2010) Phosphonium-based ionic liquids analogues and their physical properties. J Chem Eng Data 55(11):4632–4637
Abbott AP, Harris RC, Ryder KS, D’Agostino C, Gladden LF, Mantle MD (2011) Glycerol eutectics as sustainable solvent systems. Green Chem 13(1):82–90
Zhang Q, Vigier KDO, Royer S, Jérôme F (2012) Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev 41(21):7108–7146
Russell MG, Warren S (1998) Wittig reactions in water. Synthesis of new water-soluble phosphonium salts and their reactions with substituted benzaldehydes. Tetrahedron Lett 39(43):7995–7998
Su Q, Panek JS (2005) Total synthesis of (+)-leucascandrolide A. Angew Chem In Ed 44(8):1223–1225
Kong K, Moussa Z, Lee C, Romo D (2011) Total synthesis of the spirocyclic imine marine toxin (−)-gymnodimine and an unnatural C4-epimer. J Am Chem Soc 133(49):19844–19856
Spallarossa M, Wang Q, Riva R, Zhu J (2016) Synthesis of vinyl isocyanides and development of a convertible isonitrile. Org Lett 18(7):1622–1625
Wiebe DA, Burton DJ (2012) Chemoselective halogenation of 2-hydroperfluoroalkyl aldehydes. J Fluorine Chem 139:4–11
Hayakawa I, Teruya T, Kigoshi H (2006) Revised structure of zamamistatin. Tetrahedron Lett 47(2):155–158
Gentile G, Di Fabio R, Pavone F, Sabbatini FM, St-Denis Y, Zampori MG, Worby A (2007) Novel substituted tetrahydrotriazaacenaphthylene derivatives as potent CRF 1 receptor antagonists. Bioorg Med Chem 17(18):5218–5221
Kerschgens IP, Claveau E, Wanner MJ, Ingemann S, vanMaarseveen JH, Hiemstra H (2012) Total syntheses of mitragynine, paynantheine and speciogynine via an enantioselective thiourea-catalysed Pictet-Spengler reaction. Chem Commun 48(100):12243–12245
Saedi M, Mojtahedi MM, Kaamyabi S (2000) Application of microwave irradiation techniques for the Witting reaction. J Sci Iran 11:21
Mangold SL, Carpenter RT, Kiessling LL (2008) Synthesis of fluorogenic polymers for visualizing cellular internalization. Org Lett 10(14):2997–3000
Montchamp JL (2013) Phosphinate chemistry in the 21st century: a viable alternative to the use of phosphorus trichloride in organophosphorus synthesis. Acc Chem Res 47(1):77–87
Lambert WT, Burke SD (2003) Halichondrin B: synthesis of a C1–C14 Model via desymmetrization of (+)-conduritol E. Org Lett 5(4):515–518
Li Y, Zhang Q, Wittlin S, Jin HX, Wu Y (2009) Synthesis and in vitro antimalarial activity of spiro-analogues of peroxyplakoric acids. Tetrahedron 65(34):6972–6985
Fujioka H, Goto A, Otake K, Kubo O, Sawama Y, Maegawa T (2011) An unusual reaction of α-alkoxyphosphonium salts with Grignard reagents under an O2 atmosphere. Chem Commun 47(35):9894–9896
Goto A, Otake K, Kubo O, Sawama Y, Maegawa T, Fujioka H (2012) Effects of phosphorus substituents on reactions of α-alkoxyphosphonium salts with nucleophiles. Chem Eur J 18(36):11423–11432
Ley SV, Lygo B, Organ HM, Wonnacott A (1985) Wittig and Horner–Wittig coupling reactions of 2-substituted cyclic ethers and their application to spiroketal synthesis. Tetrahedron 41(18):3825–3836
Adamek J, Mazurkiewicz R, Węgrzyk A, Erfurt K (2017) 1-Imidoalkylphosphonium salts with modulated Cα-P + bond strength: synthesis and application as new active α-imidoalkylating agents. Beilstein J Org Chem 13:1446–1455
Tuckmantel W, Oshima K, Utimoto K (1986) A Convenient preparation of α-methoxyalkyltriphenylphosphonium tetrafluoroborates. Tetrahedron Lett 27:5617
Fujioka H, Goto A, Otake K, Kubo O, Yahata K, Sawama Y, Maegawa T (2010) Remarkable effect of phosphine on the reactivity of O, P-acetal—efficient substitution reaction of O, P-acetal. Chem Commun 46(22):3976–3978
Mumtaz S, Wali KS, Zaidi JH, Iqbal A, Maqsood CZ, Khan K, Perveen S (2013) Synthesis of chiral menthoxymethyl ether of phenol and substituted phenol and their use in directed ortho metalation. Lett Org Chem 10(8):578–583
Gondal HY, Cheema ZM, Zaidi JH, Yousuf S, Choudhary MI (2018) Facile synthesis of α-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2. Chem Cent J 12(1):62
Pindur U, Lutz G, Rogge M (1995) First synthesis of chiral 3-vinylindoles as 4π-components for diels-alder reactions. J Heterocycl Chem 32(1):201–206
Acknowledgements
Authors are obliged to Pakistan Science Foundation (PSF) for generous support of this research project (P-US/Chem 427).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of Interest
There is no conflict of interests among all authors.
Rights and permissions
About this article
Cite this article
Gondal, H.Y., Cheema, Z.M., Siddiqui, H. et al. Facile Efficient Synthesis of New Alkoxymethylphosphonium Tetrafluoroborates; Valuable Alternative to Their Halide Analogues. Chemistry Africa 1, 97–102 (2018). https://doi.org/10.1007/s42250-018-0009-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s42250-018-0009-5