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Efficient Organic Synthesis: What Ultrasound Makes Easier

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Organic Sonochemistry

Part of the book series: SpringerBriefs in Molecular Science ((ULSONO))

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Abstract

The application of ultrasound waves to induce and enhance chemical reactivity dates back to the pioneering studies by Richards and Loomis in the late 1920s. The long journey, now entering the twenty-first century, has been accompanied by decades of low and high research activity. But arguably, the marriage between synthesis, organic synthesis in particular, and sonochemistry has been especially fruitful from the 1980s onwards. We now realize the pluses conveyed by sonication, in terms of efficiency, acceleration and selectivity. Mechanistic switching and/or different product distribution relative to non-irradiated conditions also represent salient features observed frequently in sonochemical reactions. This chapter summarizes a series of fundamental ideas in organic sonochemistry and introduces the subject within the framework of green chemistry and sustainability. Representative examples gathered in recent literature help to appreciate the added value of sonochemistry as tool.

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References

  • Ablajan K, Kamil W, Tuoheti A, Wan-Fu S (2012) An efficient three component one-pot synthesis of 5-amino-7-aryl-7,8-dihydroxy-[1,2,4]-triazolo[4,3-a]-pyrimidine-6-carbonitriles. Molecules 17:1860–1869

    Article  CAS  Google Scholar 

  • Andraos J (2016) Complete green metrics evaluation of various routes to methyl methacrylate according to material and energy consumptions and environmental and safety impacts: test case from the chemical industry. ACS Sustain Chem Eng 4:312–323

    Article  CAS  Google Scholar 

  • Asami R, Fuchigami T, Atobe M (2008) Development of an anodic substitution reaction system using acoustic emulsification. Chem Commun 244–246

    Google Scholar 

  • Atobe M, Tateno H, Matsumura Y (2018) Applications of flow microreactors in electrosynthetic processes. Chem Rev 118:4541–4572

    Article  CAS  Google Scholar 

  • Banerjee B (2017a) Recent developments on ultrasound assisted catalyst-free organic synthesis. Ultrason Sonochem 35:1–14

    Article  CAS  Google Scholar 

  • Banerjee B (2017b) Recent developments on ultrasound-assisted one-pot multicomponent synthesis of biologically relevant heterocycles. Ultrason Sonochem 35:15–35

    Article  CAS  Google Scholar 

  • Braghiroli FL, Barboza JCS, Serra AA (2006) Sonochemical epoxidation of cyclohexene in RCN/H2O2 system. Ultrason Sonochem 13:443–445

    Article  CAS  Google Scholar 

  • Brochette-Lemoine S, Joannard D, Descotes G, Bouchu A, Queneau Y (1999) Sonocatalysis of the TEMPO-mediated oxidation of glucosides. J Mol Catal A: Chem 150:31–36

    Article  CAS  Google Scholar 

  • Brochette-Lemoine S, Trombotto S, Joannard D, Descotes G, Bouchu A, Queneau Y (2000) Ultrasound in carbohydrate chemistry: sonophysical glucose oligomerisation and sonocatalysed sucrose oxidation. Ultrason Sonochem 7:157–161

    Article  CAS  Google Scholar 

  • Bruckmann A, Krebs A, Bolm C (2008) Organocatalytic reactions: effects of ball milling, microwave and ultrasound irradiation. Green Chem 10:1131–1141

    Article  CAS  Google Scholar 

  • Bujak P, Bartczak P, Polanski J (2012) Highly efficient room-temperature oxidation of cyclohexene and d-glucose over nanogold Au/SiO2 in water. J Catal 295:15–21

    Article  CAS  Google Scholar 

  • Cella R, Stefani H (2009) Ultrasound in heterocycles chemistry. Tetrahedron 65:2619–2641

    Article  CAS  Google Scholar 

  • Chatel G, Goux-Henry C, Mirabaud A, Rossi T, Kardos N, Andrioletti B, Draye M (2012) H2O2/NaHCO3-mediated enantioselective epoxidation of olefins in NTf2-based ionic liquids and under ultrasound. J Catal 291:127–132

    Article  CAS  Google Scholar 

  • Chatel G, MacFarlane DR (2014) Ionic liquids and ultrasound in combination: synergies and challenges. Chem Soc Rev 43:8132–8149

    Article  CAS  Google Scholar 

  • Chatel G, De Oliveira Vigier K, Jérôme F (2014) Sonochemistry: what potential for conversion of lignocellulosic biomass into platform chemicals? Chemsuschem 7:2774–2787

    Article  CAS  Google Scholar 

  • Chatel G (2017) Sonochemistry. New opportunities for green chemistry (Chap. 5). World Scientific Publishing, Singapore, pp 59–145

    Google Scholar 

  • Chen D, Sharma SK, Mudhoo A (2011) Handbook on applications of ultrasound. Sonochemistry for sustainability. CRC Press, Boca Raton, FL

    Google Scholar 

  • Chermahini AN, Teimouri A, Momenbeik F, Zarei A, Dalimarab Z, Ghaedi A, Roosta M (2010) Clay-catalyzed synthesis of 5-substituted-1-H-tetrazoles. J Heterocycl Chem 47:913–922

    Article  CAS  Google Scholar 

  • Cintas P, Barge A, Tagliapietra S, Boffa L, Cravotto G (2010) Alkyne-azide click reaction catalyzed by metallic copper under ultrasound. Nat Protocol 5:607–611

    Article  CAS  Google Scholar 

  • Cintas P, Palmisano G, Cravotto G (2011) Power ultrasound in metal-assisted synthesis: from classical Barbier-like reactions to click chemistry. Ultrason Sonochem 18:836–841

    Article  CAS  Google Scholar 

  • Cintas P (2016) Ultrasound and green chemistry—further comments. Ultrason Sonochem 28:257–258

    Article  CAS  Google Scholar 

  • Constable DJC, Curzons AD, Cunningham VL (2002) Metrics to green chemistry: which are the best? Green Chem 4:521–527

    Article  CAS  Google Scholar 

  • Datta B, Pasha MA (2012) Glycine catalyzed convenient synthesis of 2-amino-4H-chromenes in aqueous medium under sonic condition. Ultrason Sonochem 19:725–728

    Article  CAS  Google Scholar 

  • Disselkamp RS, Judd KM, Hart TR, Peden CHF, Posakony GJ, Bond LJ (2004) A comparison between conventional and ultrasound-mediated heterogeneous catalysis: hydrogenation of 3-buten-ol aqueous solutions. J Catal 221:347–353

    Article  CAS  Google Scholar 

  • Domini CE, Álvarez MB, Silbestri GE, Cravotto G, Cintas P (2017) Merging metallic catalysts and sonication: a periodic table overview. Catalysts 7:121. https://doi.org/10.3390/catal7040121

    Article  CAS  Google Scholar 

  • Et Taouil A, Lallemand F, Hallez L, Hihn JY (2010) Electropolymerization of pyrrole on oxidizable metal under high frequency ultrasound irradiation. Application of focused beam to a selective masking technique. Electrochim Acta 55:9137–9145

    Article  CAS  Google Scholar 

  • Et Taouil A, Lallemand F, Hihn JY, Melot JM, Blondeau-Patissier V, Lakard B (2011) Doping properties of PEDOT films electrosynthesized under high frequency ultrasound irradiation. Ultrason Sonochem 18:140–148

    Article  CAS  Google Scholar 

  • Fegade SL, Tremblay JP (2017) Misinterpretation of green chemistry. Ultrason Sonochem 37:686–687

    Article  CAS  Google Scholar 

  • Fitzpatrick DE, Battilocchio C, Ley SV (2016) Enabling technologies for the future of chemical synthesis. ACS Cent Sci 2:131–138

    Article  CAS  Google Scholar 

  • Fritze UF, von Delius M (2016) Dynamic disulfide metathesis induced by ultrasound. Chem Commun 52:6363–6366

    Article  CAS  Google Scholar 

  • Gallego-Juárez JA, Graff KF (2015) Power ultrasonics. Applications of high-intensity ultrasound. Elsevier, Amsterdam

    Google Scholar 

  • Gemoets HPL, Su Y, Shang M, Hessel V, Luque R, Noël T (2016) Liquid phase oxidation chemistry in continuous-flow microreactors. Chem Soc Rev 45:83–117

    Article  CAS  Google Scholar 

  • González-Paz RJ, Lluch C, Lligadas G, Ronda JC, Galià M, Cádiz V (2011) A green approach toward oleic- and undecylenic acid-derived polyurethanes. J Polym Sci A Polym Chem 49:2407–2416

    Article  Google Scholar 

  • Gronnow MJ, White RJ, Clark JH, Macquarrie DJ (2005) Energy efficiency in chemical reactions: a comparative study of different reaction techniques. Org Process Res Dev 9:516–518

    Article  CAS  Google Scholar 

  • Gułajski Ł, Śledź P, Lupa A, Grela K (2008) Olefin metathesis in water using acoustic emulsification. Green Chem 10:271–274

    Article  Google Scholar 

  • Hessel V, Cravotto G, Fitzpatrick P, Patil BS, Lang J, Bonrath W (2013) Industrial applications of plasma, microwave and ultrasound techniques: nitrogen fixation and hydrogenation reactions. Chem Eng Process 71:19–30

    Article  CAS  Google Scholar 

  • Jaiswal PK, Sharma V, Prikhodko J, Mashevskaya IV, Chaudhary S (2017) “On water” ultrasound-assisted one-pot efficient synthesis of functionalized 2-oxo-benzo[1,4]oxazines: first application to the synthesis of anticancer indole alkaloid Cephalandole A. Tetrahedron Lett 58:2077–2083

    Article  CAS  Google Scholar 

  • Jiménez-González C, Constable DJC (2011) Green chemistry and engineering. A practical design approach. Wiley, New York, pp 79–101

    Google Scholar 

  • Jiménez-González C, Constable DJC, Ponder CS (2012) Evaluating the greenness of chemical processes and products in the pharmaceutical industry—a green metrics primer. Chem Soc Rev 41:1485–1498

    Article  Google Scholar 

  • Kamble S, Kumbhar A, Rashinkar G, Barge M, Salunkhe R (2012) Ultrasound promoted efficient and green synthesis of β-amino carbonyl compounds in aqueous hydrotropic medium. Ultrason Sonochem 19:812–815

    Article  CAS  Google Scholar 

  • Kanchithalaivan S, Sumesh RV, Kumar RR (2014) Ultrasound-assisted sequential multicomponent strategy for the combinatorial synthesis of novel comarin hybrids. ACS Comb Sci 16:566–572

    Article  CAS  Google Scholar 

  • Li C, Zhao X, Wang A, Huber GW, Zhang T (2015) Catalytic transformation of lignin for the production of chemicals and fuels. Chem Rev 115:11559–11624

    Article  CAS  Google Scholar 

  • Li CJ (2017) Exploration of new chemical reactivities for sustainable molecular transformations. Chem 1:423–437

    Article  Google Scholar 

  • Li JT, Yin Y, Sun MX (2010) An efficient one-pot synthesis of 2,3-epoxy-1,3-diaryl-1-propanone directly from acetophenones and aromatic aldehydes under ultrasound irradiation. Ultrason Sonochem 17:363–366

    Article  CAS  Google Scholar 

  • Luche JL (1998) Synthetic organic sonochemistry. Plenum Press, New York

    Book  Google Scholar 

  • Luche JL (1993) Sonochemistry. From experiment to theoretical considerations. In: Mason TJ (ed) Advances in sonochemistry, vol 3. JAI Press Ltd, London, pp 85–124

    Google Scholar 

  • Lupacchini M, Mascitti A, Giachi G, Tonucci L, d’Alessandro N, Martinez J, Colacino E (2017) Sonochemistry in non-conventional, green solvents or solvent-free reactions. Tetrahedron 73:609–653

    Article  CAS  Google Scholar 

  • Marzag H, Alaoui S, Amdouni H, Martin AR, Bougrin K, Benhida R (2015) Efficient and selective azidation of per-O-acetylated sugars using ultrasound activation: application to the one-pot synthesis of 1,2,3-triazole glycosides. New J Chem 39:5437–5444

    Article  CAS  Google Scholar 

  • Mitsudo K, Kurimoto Y, Yoshioka K, Suga S (2018) Miniaturization and combinatorial approach in organic electrochemistry. Chem Rev 118:5985–5999

    Article  CAS  Google Scholar 

  • Moeller KD (2018) Using physical organic chemistry to shape the course of electrochemical reactions. Chem Rev 118:4817–4833

    Article  CAS  Google Scholar 

  • Mojtahedi MM, Abaee MS (2011) Ultrasound applications in synthetic organic chemistry. In: Chen D, Sharma SK, Mudhoo A (eds) Handbook on applications of ultrasound. Sonochemistry for sustainability (Chap. 12). CRC Press, Boca Raton, FL, pp 281–321

    Google Scholar 

  • More PA, Shankarling GS (2017) Energy efficient Pfitzinger reaction: a novel strategy using a surfactant catalyst. New J Chem 41:12380–12383

    Article  CAS  Google Scholar 

  • Park JC, Kim AY, Kim JY, Park S, Park KH, Song H (2012) ZnO-CuO core-branch nanocatalysts for ultrasound-assisted azide-alkyne cycloaddition reactions. Chem Commun 48:8484–8486

    Article  CAS  Google Scholar 

  • Pollet BG, Hihn JY (2011) Sonoelectrochemistry: from theory to applications. In: Chen D, Sharma SK, Mudhoo A (eds) Handbook on applications of ultrasound. Sonochemistry for sustainability (Chap. 24). CRC Press, Boca Raton, FL, pp 623–657

    Google Scholar 

  • Rinsant D, Chatel G, Jérôme F (2014) Efficient and selective oxidation of D-glucose into gluconic acid under low-frequency ultrasonic irradiation. ChemCatChem 6:3355–3359

    Article  CAS  Google Scholar 

  • Rogozinska M, Adamkiewicz A, Mlynarski J (2011) Efficient “on water” organocatalytic protocol for the synthesis of optically pure warfarin anticoagulant. Green Chem 13:1155–1157

    Article  CAS  Google Scholar 

  • Santos RG, Xavier NM, Bordado JC, Rauter AP (2013) Efficient and first regio- and stereoselective direct C-glycosylation of a flavanone catalyzed by Pr(OTf)3 under conventional heating or ultrasound irradiation. Eur J Org Chem 1441–1447

    Article  CAS  Google Scholar 

  • Sari O, Hamada M, Roy V, Nolan SP, Agrofoglio LA (2013) The preparation of trisubstituted alkenyl nucleoside phosphonates under ultrasound-assisted olefin cross-metathesis. Org Lett 15:4390–4393

    Article  CAS  Google Scholar 

  • Shingare MS, Shingate BB (2011) Ultrasound in synthetic applications and organic chemistry. In: Chen D, Sharma SK, Mudhoo A (eds) Handbook on applications of ultrasound. Sonochemistry for sustainability (Chap. 10). CRC Press, Boca Raton, FL, pp 213–261

    Google Scholar 

  • Skinner EK, Whiffin FM, Price GJ (2012) Room temperature sonochemical initiation of thiol-ene reactions. Chem Commun 48:6800–6802

    Article  CAS  Google Scholar 

  • Sunaga T, Atobe M, Inagi S, Fuchigami T (2009) Highly efficient and selective electrochemical fluorination of organosulfur compounds in Et3N·3HF ionic liquid under ultrasonication. Chem Commun 956–958

    Google Scholar 

  • Tabasso S, Carnaroglio D, Calcio Gaudino E, Cravotto G (2015) Microwave, ultrasound and ball mill procedures for bio-waste valorisation. Green Chem 17:684–693

    Article  CAS  Google Scholar 

  • Tagliapietra S, Calcio Gaudino E, Cravotto G (2015) The use of power ultrasound for organic synthesis in green chemistry. In: Gallego-Juárez JA, Graff KF (eds) Power ultrasonics. Applications of high-intensity ultrasound (Chap. 33). Elsevier, Amsterdam, pp 997–1022

    Google Scholar 

  • Toukoniitty B, Kuusisto J, Mikkola JP, Salmi T, Murzin DY (2005) Effect of ultrasound on catalytic hydrogenation of D-fructose to D-mannitol. Ind Eng Chem Res 44:9370–9375

    Article  CAS  Google Scholar 

  • Tripathi B, Paniwnyk L, Cherkasov N, Ibhadon AO, Lana-Villareal T, Gómez R (2015) Ultrasound-assisted selective hydrogenation of C-5 acetylene alcohols with Lindlar catalysts. Ultrason Sonochem 26:445–451

    Article  CAS  Google Scholar 

  • Wadhawan JD, Marken F, Compton RG, Bull SD, Davies SG (2001) Sono-emulsion electrosynthesis: electrode-insensitive Kolbe reactions. Chem Commun 87–88

    Google Scholar 

  • Wet-Osot S, Duangkamol C, Phakhodee W, Pattarawarapan M (2016) Ultrasound-assisted solvent-free parallel synthesis of 3-arylcoumarins using N-acylbenzotriazoles. ACS Comb Sci 18:279–282

    Article  CAS  Google Scholar 

  • Wood RJ, Lee J, Bussemaker MJ (2017) A parametric review of sonochemistry: control and augmentation of sonochemical activity in aqueous solutions. Ultrason Sonochem 38:351–370

    Article  CAS  Google Scholar 

  • Yan M, Kawamata Y, Baran PS (2017) Synthetic organic electrochemical methods since 2000: on the verge of a renaissance. Chem Rev 117:13230–13319

    Article  CAS  Google Scholar 

  • Yu SJ, Zhu C, Bian Q, Cui C, Du XJ, Li ZM, Zhao WG (2014) Novel ultrasound-promoted parallel synthesis of trifluoroatrolactamide library via a one-pot Passerini/hydrolysis reaction sequence and their fungicidal activities. ACS Comb Sci 16:17–23

    Article  CAS  Google Scholar 

  • Zhang P, Yang M, Lu X (2007) Epoxidation of cyclohexene with oxygen in ultrasound airlift loop reactor. Chin J Chem Eng 15:196–199

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. LCME/SCeM, Université de Savoie Mont Blanc, Paris, France

    Jean-Marc Lévêque

  2. Dipartimento di Scienza e Tecnologia del Farmaco, Universitá di Torino, Turin, Italy

    Giancarlo Cravotto

  3. Departement de Chimie, Unité de Chimie Environnementale et Interactions sur le Vivant, Dunkerque, France

    François Delattre

  4. Departamento Química Orgánica e Inorgánica, Facultad de Ciencias, University of Extremadura, Badajoz, Spain

    Pedro Cintas

Authors
  1. Jean-Marc Lévêque
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  2. Giancarlo Cravotto
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  3. François Delattre
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  4. Pedro Cintas
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Correspondence to Jean-Marc Lévêque .

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Lévêque, JM., Cravotto, G., Delattre, F., Cintas, P. (2018). Efficient Organic Synthesis: What Ultrasound Makes Easier. In: Organic Sonochemistry. SpringerBriefs in Molecular Science(). Springer, Cham. https://doi.org/10.1007/978-3-319-98554-1_2

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