Facile synthesis of α-alkoxymethyltriphenylphosphonium iodides: new application of PPh3/I2

Springer Science and Business Media LLC - Tập 12 - Trang 1-10 - 2018
Humaira Yasmeen Gondal1, Zain Maqsood Cheema2, Javid Hussain Zaidi3, Sammer Yousuf4, M. Iqbal Choudhary4
1Department of Chemistry, University of Sargodha, Sargodha, Pakistan
2Department of Chemistry, University of Sheffield, Sheffield, UK
3Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan
4H.E.J. Research Institute of Chemistry, ICCBS, University of Karachi, Karachi, Pakistan

Tóm tắt

An efficient one pot method for the synthesis of α-alkoxymethylphosphonium iodides is developed by using PPh3/I2 combination at room temperature. Reaction conditions are found general to synthesize wide range of structurally variant alkoxymethylphosphonium iodides in high yield (70–91%). These new functionalized phosphonium salts are further used in stereoselective synthesis of vinyl ethers as well as in carbon homologation of aldehydes.

Tài liệu tham khảo

Bahadori L, Manan NS, Chakrabarti MH, Hashim MA, Mjalli FS, AlNashef IM, Hussain MA, Low CT (2013) The electrochemical behaviour of ferrocene in deep eutectic solvents based on quaternary ammonium and phosphonium salts. Phys Chem Chem Phys 15(5):1707–1714 Hayyan M, Hashim MA, Al-Saadi MA, Hayyan A, AlNashef IM, Mirghani ME (2013) Assessment of cytotoxicity and toxicity for phosphonium-based deep eutectic solvents. Chemosphere 93(2):455–459 Marsden SP (2009) Organic synthesis: the Wittig reaction cleans up. Nat Chem 1(9):685 Zaragoza F (2002) One-step conversion of alcohols into nitriles with simultaneous two-carbon chain elongation. (Cyanomethyl) trimethylphosphonium iodide as a reagent with a dual mode of action. J Org Chem 67(14):4963–4964 Hayyan A, Hashim MA, Mjalli FS, Hayyan M, AlNashef IM (2013) A novel phosphonium-based deep eutectic catalyst for biodiesel production from industrial low grade crude palm oil. Chem Eng Sci 5(92):81–88 Wang P, Liao S, Zhu JB, Tang Y (2014) Double γ-alkylation of allylic phosphorus ylides: a unique access to oxa-bicyclic [3.3.0] diene skeletons. Chem Comm 50(7):808–810 Okada H, Mori T, Saikawa Y, Nakata M (2009) Formation of α-hydroxyketones via irregular Wittig reaction. Tetrahedron Lett 50(12):1276–1278 Gentile G, Di Fabio R, Pavone F, Sabbatini FM, St-Denis Y, Zampori MG, Vitulli G, Worby A (2007) Novel substituted tetrahydrotriazaacenaphthylene derivatives as potent CRF 1 receptor antagonists. Bioorg Med Chem Lett 17(18):5218–5221 Fröhlich J, Sauter F, Hametner C, Pfalz M (2009) Synthesis of novel 3-heterospiro [5.5] undecanes. ARKIVOC 1(6):298–308 Wiebe DA, Burton DJ (2012) Chemoselective halogenation of 2-hydroperfluoroalkyl aldehydes. J Fluorine Chem 1(139):4–11 Ko KY, Wagner S, Yang SH, Furkert DP, Brimble MA (2015) Improved synthesis of the unnatural amino acids AHMOD and AMD, components of the anticancer peptaibol culicinin D. J Org Chem 80(17):8631–8636 Pindur U, Lutz G, Rogge M (1995) First synthesis of chiral 3-vinylindoles as 4π-components for Diels–Alder reactions. J Heterocyclic Chem 32(1):201–206 Lambert WT, Hanson GH, Benayoud F, Burke SD (2005) Halichondrin B: synthesis of the C1–C22 subunit. J Org Chem 70(23):9382–9398 Assefa H, Nimrod A, Walker L, Sindelar R (2001) Enantioselective synthesis and complement inhibitory assay of A/B-ring partial analogues of oleanolic acid. Bioorg Med Chem Lett 11(13):1619–1623 Treu M, Jordis U (2002) 4a,5,9,10,11,12-Hexahydro-6H-benzo[a]cyclohepta[hi] benzofuran-synthesis of unnatural galanthamine analogs. Molecules 7(4):374–381 Poschalko A, Welzig S, Treu M, Nerdinger S, Mereiter K, Jordis U (2002) Synthesis of (±)-6H-benzofuro[3a,3,2, ef][3]benzazepine: an unnatural analog of (−)-galanthamine. Tetrahedron 58(8):1513–1518 Mangold SL, Carpenter RT, Kiessling LL (2008) Synthesis of fluorogenic polymers for visualizing cellular internalization. Org Lett 10(14):2997–3000 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 Comm 46(22):3976–3978 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 Comm 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 Deng Z, Lin JH, Xiao JC (2016) Nucleophilic arylation with tetraarylphosphonium salts. Nat Commun 29(7):10337 Szymczyk M (2017) Unexpected course of Wittig reaction when using cinnamylaldehyde as a substrate. Phosphorus Sulfur 192(3):264–266 Wittig G, Schlosser M (1961) Über die Herstellung von Vinyläthern, Vinylthioäthern und Vinylhalogeniden auf der Phosphylen-Basis; IV. Mitteil. über Phosphin-alkylene als olefinbildende Reagenzien. Eur J Inorg Chem 94(5):1373–1383 Mazurek MA (1978) A new efficient synthesis of iodomethyl methyl ether. Synthesis 08:588–589 Morcillo SP, Alvarez de Cienfuegos L, Mota AJ, Justicia J, Robles R (2011) Mild method for the selective esterification of carboxylic acids based on the Garegg–Samuelsson reaction. J Org Chem 76(7):2277–2281 Xu F, Wang NG, Tian YP, Chen YM, Liu WC (2012) Ph3P/I2-catalyzed beckmann rearrangement of ketoximes into amides. Synth Commun 42(23):3532–3539 Lockman JW, Klimova Y, Anderson MB, Willardsen JA (2012) Synthesis of substituted quinazolines: application to the synthesis of verubulin. Synth Commun 42(12):1715–1723 Kumar A, Akula HK, Lakshman MK (2010) Simple synthesis of amides and Weinreb amides using PPh3 or polymer-supported PPh3 and iodine. Eur J Org Chem 2010(14):2709–2715 Samimi HA, Kiyani H, Shams Z (2013) Stereo-controlled deamination of ketoaziridines using Ph3P/I2. J Chem Res 37(5):282–284 Duangkamol C, Wangngae S, Pattarawarapan M, Phakhodee W (2014) Acyloxyphosphonium versus aminophosphonium intermediates: application to the synthesis of N-acylbenzotriazoles. Eur J Org Chem 32:7109–7112 Wangngae S, Duangkamol C, Pattarawarapan M, Phakhodee W (2015) Significance of reagent addition sequence in the amidation of carboxylic acids mediated by PPh3 and I2. RSC Adv 5(33):25789–25793 Sun G, Lv X, Zhang Y, Lei M, Hu L (2017) Palladium-catalyzed formylation of Aryl iodides with HCOOH as CO source. Org let 19(16):4235–4238 Mumtaz S, Wali KS, Zaidi J, Iqbal A, Maqsood CZ, Mohammed KK, 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 Pruess DL, Scannell JP, Kellett M, Ax HA, Janecek J, Williams TH, Berger J (1947) Antimetabolites produced by microorganisms. X. J Antibio 27(4):229–233 González-Coloma A, Escoubas P, Mizutani J, Lajide L (1994) Insect growth inhibitors from Machilus japonica. Phytochemistry 35(3):607–610 Nebois P, Greene AE (1999) Novel enantioselective approach to γ-lactams from chiral enol ethers: synthesis of (−)-statine. J Org Chem 61(16):5210–5211 Corey EJ (2002) Catalytic enantioselective Diels–Alder reactions: methods, mechanistic fundamentals, pathways, and applications. Angew Chem Int Ed 41:1650–1667 Tian J, Moeller Kevin D (2005) Electrochemically assisted Heck reactions. Org Lett 24:5381–5383 Miyaura N, Maeda K, Suginome H (1982) Palladium-catalyzed cross-coupling of (2-ethoxyvinyl) boranes with aryl and benzyl halides. A new method for conversion of organic halides into aldehydes with two more carbon atoms. J Org Chem 47(11):2117–2120 Fuwa H, Sasaki M (2007) An efficient method for the synthesis of enol ethers and enecarbamates. Total syntheses of isoindolobenzazepine alkaloids, lennoxamine and chilenine. Org Biomol Chem 5(12):1849–1853 Satoh M, Miyaura N, Suzuki A (1987) Palladium-catalyzed cross-coupling reaction of (1-ethoxy-1-alken-2-yl) boranes with ortho-functionalized iodoarenes. A novel and convenient synthesis of benzo-fused heteroaromatic compounds. Synthesis 04:373–377 Sakamoto T, Kondo Y, Yasuhara A, Yamanaka H (1991) Condensed heteroaromatic ring systems. XVIII. Palladium-catalyzed cross-coupling reaction of aryl bromides with (Z)-1-ethoxy-2-tributylstannylethene and its utilization for construction of condensed heteroaromatics. Tetrahedron 47:1877–1886 Beletskaya IP, Cheprakov AV (2000) The Heck reaction as a sharpening stone of palladium catalysis. Chem Rev 100:3009–3066 Fürstner A (2000) Olefin metathesis and beyond. Angew Chem Int Ed 39:3012–3043 Rehbein J, Hiersemann M (2013) Claisen rearrangement of aliphatic allyl vinyl ethers from 1912 to 2012: 100 years of electrophilic catalysis. Synthesis 45(09):1121–1159 Hansen HJ, Schmid H (1974) Stereochemie von [3.3]-und [5.5]-sigmatropischen umlagerungen. Tetrahedron 30(13):1959–1969 He W, Herrick IR, Atesin TA, Caruana PA, Kellenberger CA, Frontier AJ (2008) Polarizing the Nazarov cyclization: the impact of dienone substitution pattern on reactivity and selectivity. J Am Chem Soc 130(3):1003–1011 Malona JA, Cariou K, Frontier AJ (2009) Nazarov cyclization initiated by peracid oxidation: the total synthesis of (±)-rocaglamide. J Am Chem Soc 131(22):7560–7561 Aoshima S, Kanaoka S (2009) A renaissance in living cationic polymerization. Chem Rev 109(11):5245–5287 Friesen RW (2001) Generation and reactivity of α-metalated vinyl ethers. J Chem Soc Perkin Trans 17:1969–2001 Dehli JR, Legros J, Bolm C (2005) Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions. Chem Commun 8:973–986 Winternheimer DJ, Shade RE, Merlic CA (2010) Methods for vinyl ether synthesis. Synthesis 15:2497–2511 Wan Z, Jones CD, Koenig TM, Pu YJ, Mitchell D (2003) Vinyl aryl ethers from copper-catalyzed coupling of vinyl halides and phenols. Tetrahedron Lett 44(45):8257–8259 Shade RE, Hyde AM, Olsen JC, Merlic CA (2010) Copper-promoted coupling of vinyl boronates and alcohols: a mild synthesis of allyl vinyl ethers. J Am Chem Soc 132(4):1202–1203 Kondo M, Kochi T, Kakiuchi F (2010) Rhodium-catalyzed anti-Markovnikov intermolecular hydroalkoxylation of terminal acetylenes. J Am Chem Soc 133(1):32–34 Moyano A, Charbonnier F, Greene AE (1987) Simple preparation of chiral acetylenic ethers. J Org Chem 52(13):2919–2922 Keegstra MA (1992) Copper catalysed preparation of vinyl ethers from unactivated vinylic halides. Tetrahedron 48(13):2681–2690 Ronson TO, Voelkel MH, Taylor RJ, Fairlamb IJ (2015) Macrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems. Chem Commun 51(38):8034–8036 Lam PY, Vincent G, Bonne D, Clark CG (2003) Copper-promoted/catalyzed C–N and C–O bond cross-coupling with vinylboronic acid and its utilities. Tetrahedron Lett 44(26):4927–4931 Dussault PH, Sloss DG, Symonsbergen DJ (1998) Application of the Sonogashira coupling reaction to the stereoselective synthesis of chiral 1,3-dienol ethers. Synlett 12:1387–1389 Maeda K, Shinokubo H, Oshima K, Utimoto K (1996) Stereoselective synthesis of allyl vinyl ethers from silyl enol ethers. J Org Chem 61(7):2262–2263 Engesser T, Brückner R (2017) Synthesis of trans configured enol ethers by a sequence of syn selective glycolate aldol addition, hydrolysis, and grob fragmentation. Eur J Org Chem 38:5789–5794 Kulkarni MG, Rasne RM, Davawala SI, Doke AK (2002) Allyl vinyl ethers via Wittig olefination: a short and efficient synthesis of (±)-mesembrine. Tetrahedron Lett 43(12):2297–2298 Balti M, Efrit ML, Leadbeater NE (2016) Preparation of vinyl ethers using a Wittig approach, and their subsequent hydrogenation employing continuous-flow processing. Tetrahedron Lett 57(16):1804–1806