Abstract
For reasons of economy and pollution, solvent-free methods are of great interest in order to modernize classical procedures making them more clean, safe and easy to perform. Reactions on solid mineral supports, reactions without any solvent/support or catalyst, and solid-liquid phase transfer catalysis can be thus employed with noticeable increases in reactivity and selectivity. A comprehensive review of these techniques is presented here. These methodologies can moreover be improved to take advantage of microwave activation as a beneficial alternative to conventional heating under safe and efficient conditions with large enhancements in yields and savings in time.
Keywords
- Mineral solid supports
- Phase transfer catalysis
- Solid state reactions
- Reactivity
- Selectivity
- Microwave activation
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References
Keinan E, Mazur Y (1977) J. Am Chem Soc 99:3861
Laszlo P (1987) In: Preparative chemistry using supported reagents. Academic Press, London
Smith K (1992) In: Solid support and catalysts in organic synthesis. Ellis Horwood PTR Prentice Hall, Chichester
Kabalka GW, Pagni RM (1997) Tetrahedron 53:7999
Toda F (1993) Synlett 304
Toda F (1995) Acc Chem Res 28:480
Starks CM (1971) J Am Chem Soc 93:195
Bram. G, Loupy A, Sansoulet J (1985) Israel J Chem 26:291
Bram G, Galons H, Labidalle S, Loupy A, Miocque M, Petit A, Pigeon P, Sansoulet J ( 1989) Bull Soc Chim Fr 247
Foucaud A, Bram G, Loupy A (1993) In: Preparative chemistry using supported reagents, Academic Press, London, chap 17, p 317
Hondrogiannis G, Than CL, Pagni RM, Kabalka GW, Herold S, Ross E, Green J, Mc Ginnis M (1994) Tetrahedron Lett 35:6211
Bram G, D’Incan E, Loupy A ( 1982) New J Chem 573, 689
Loupy A, Seyden-Penne J (1980) Tetrahedron 36:1937
Pagni RM, Kabalka GW, Boothe R, Gaetano K, Stewart LJ, Conaway R, Dial C, Gray D, Larson S, Luidhardt T (1988) J Org Chem 53:4477
Kropp PJ, Daus KA, Tubergen MW, Kepler KD, Wilson VP, Craig SL, Baillargeon MM, Breton GW (1993) J Am Chem Soc 115:3071
Czech B, Quici S, Regen SL (1980) Synthesis 113
Tan CL, Pagni RM, Kabalka GW, Hillmyer M, Woosley J (1992) Tetrahedron Lett 33:7709
Bodwell GJ, Hougton TJ, Koury HE, Yarlagadda B (1995) Synlett 751
Parks GA (1965) Chem Rev 65:177
Varma RS, Varma M (1992) Tetrahedron Lett 33:5937
Texier-Boullet F (1985) Synthesis 679
Rosini G, Ballini R, Sorrenti P (1983) Tetrahedron 39:4127
Ranu BC, Bhars S (1992) Tetrahedron 48:1327
Loupy A, Tchoubar B (1992) In: Salt effects in organic and organometallic chemistry, VCH, Weinheim, p 37
Clark JH (1980) Chem Rev 80:429
Yamawaki J, Ando T (1979) Chem Lett 755
Villemin D, Ricard M (1984) Tetrahedron Lett 39:1059
Oussaïd A, Loupy A unpublished results; Oussaïd A ( 1997) PhD thesis, Orsay, Paris-South University
Ando T, Kawate T, Ichihara J, Hanafusa T (1984) Chem Lett 725
Anufriev VP, Norikov V (1995) Tetrahedron Lett 36:2515; Ando T, Kawate T, Ichihara J, Hanafusa T (1983) Bull Soc Chim Jpn 56:1885
Ando T, Sumi S, Kawate T, Ichihara J, Hanafusa T ( 1984) J Chem Soc Chem Commun 439
Posner GH, Rogers DZ (1977) J Am Chem Soc 99:8208,8214
Ranu B, Majee A, Das AR (1995) Synth Commun 25:263
Dhavale DD, Sindkhedkar MD, Mali RS (1995) J Chem Res S 414
Pagni RM, Kabalka GW, Hondrogiannis G, Bains S, Anosike P, Kurt R (1993) Tetrahedron 49:6743
Bains S, Pagni RM, Kabalka GW, Palla C ( 1994) Tetrahedron: Asymmetry 5:2263
Kamitori Y, Hojo M, Masuda R, Yoshida T ( 1985) Tetrahedron Lett 26:4767
Kodomari M, Sakamoto T, Yoshitomi S (1990) J Chem Soc Chem Commun 701
Ranu BC, Ghosh K, Jana U (1996) J Org Chem 61:9546
Breton GW, Kurtz MJ, Kurtz SL (1997) Tetrahedron Lett 38:3825
Farwaha R, de Mayo P, Schauble JH, Toong YC (1985) J Org Chem 50:149
Slayton RM, Franklin NR, Tro NJ (1996) J Phys Chem 100:15551
Santaniello E (1993) In: Preparative chemistry using supported reagents. Academic Press, London, chap 18, p 345
Ranu BC, Sarkar A, Saha M, Chakraborty R (1994) Tetrahedron 50:6579; Ranu BC, Majee A, Sarkar A (1998) J Org Chem 63:370
Clark JH, Cork DG (1983) J Chem Soc Perkin Trans 1 2253
Bram G, Loupy A (1993) In: Preparative chemistry using supported reagents. Academic Press, London, chap 20, p 387
Kotushi H, Shimanouchi T, Oshima R, Fujiwara S (1998) Tetrahedron 54:2709
Veselovsky VV, Gybin AS, Lozanova AV, Moiseenkov AM, Smit WA, Caple R (1988) Tetrahedron Lett 29:175
Patil VJ, Mävers U ( 1996) Tetrahedron Lett 37:1281
Bram G, D’Incan E, Loupy A (1981) J Chem Soc Chem Commun 1066
Barry J, Bram G, Decodts G, Loupy A, Pigeon P, Sansoulet J (1983) Tetrahedron 39: 2669
Bram J, Loupy A, Roux-Schmitt MC, Sansoulet J, Strzalko T, Seyden-Penne J (1987) Synthesis 56
Huang B, Gupton JT, Hansen KC, Idoux JP (1996) Synth Commun 26:165
Balogh M, Laszlo P (1993) In: Organic chemistry using clays, reactivity and structure concepts in organic chemistry, vol 29. Springer, Berlin Heidelberg New York
Izumi K, Urabe K, Onaka M (1992) In: Zeolite, clay and heteropoly acids in organic reactions, VCH, Weinhein, chap 1, p 21
Toshima K, Ishizuka T, Matsuo G, Nakata M (1995) Synlett 306
Toshima K, Miyamoto N, Matsuo G, Nakata M, Matsumura S (1996) J Chem Soc Chem Commun 1379
Toshima K, Ushiki Y, Matsuo G, Matsumara S ( 1997) Tetrahedron Lett 38:7375
Kellendonk FJA, Heinerman JJL, Van Santen RA (1987) In: Preparative chemistry using supported reagents. Academic Press, London, chap 23, p 455
Theng BKG (1979) In: Formation and properties of clay-polymer complexes, Elsevier, Amsterdam
Diddams P (1992) In: Solid supports and catalysts in organic synthesis, Ellis Horwood PTR Prentice Hall, Chichester, chap 1, p 23
Ben alloum A, Labiad B, Villemin D (1989) J Chem Soc Chem Commun 386
Pério B, Dozias MJ, Jacquault P, Hamelin J (1997) Tetrahedron Lett 38:7867
Devic M, Schirmann JP, Decarreau A, Bram G, Loupy A, Petit A (1991 ) New J Chem 15:949
Bram G, Loupy A, Majdoub M, Petit A (1991) Chem Ind (London) 396
Cornélis A, Dony C, Laszlo P, Nsunda KM (1991) Tetrahedron Lett 32:1423; Clark JH, Kybett AP, Mac Quarrie DJ, Barlow SJ, Landon P (1989) J Chem Soc Chem Commun 1353
Cornélis A, Gestermans A, Laszlo P, Mathy A, Zieba I (1990) CatalLett 6:103
Bram G, Loupy A, Villemin D (1992) In: Solid supports and catalysts in organic synthesis, Ellis Horwood PTR Prentice Hall, Chichester, chap 12, p 301
Corey EJ, Seebach D (1966) J Org Chem 31:4097
Loupy A, Sansoulet J, Harris AR (1989) Synth Commun 19:2939
Harris AR (1988) Synth Commun 18:659
Toda F, Yagi M, Kiyoshige K (1988) J Chem Soc Chem Commun 958
Toda F, Tanaka K, Hamai K (1990) J Chem Soc Perkin Trans 1 3207
Kammoun N, Le Bigot Y, Delmas M, Boutevin B (1997) Synth Commun 27:2777
Im J, Kim S, Hahn B, Toda F ( 1997) Tetrahedron Lett 38:451
Toda F, Aakai H ( 1990) J Org Chem 55:3446
Rajagopal D, Rajagopalan K, Swaminathan S (1996) Tetrahedron: Asymmetry 7:2189
Keller P (1987) Macromolecules 20:462; Majdoub M (1998) PhD thesis, University Tunis II
Strzelecka H, Jallabert C, Veber M, Malthête J (1988) Mol Cryst Liq Cryst 136:347; Bayle JP, Bui E, Perez F, Courtieu J (1989) Bull Soc Chim Fr 532
Loupy A, Sansoulet J, Vaziri-Zand F (1987) Bull Soc Chim Fr 1027
Barry J, Bram G, Decodts G, Loupy A, Orange C, Petit A, Sansoulet J (1985) Synthesis 40
Loupy A, Sansoulet J, Pedoussaut M (1986) J Org Chem 51:740
Le Ngoc T, Duong-Lieu H, Nguyen-Ba H, Radhakrishna AS, Singh BB, Loupy A (1993) Synth Commun 23:1379
Diez-Barra E, De la Hoz A, Diaz-Ortiz A, Prieto P (1992) Synlett 893
Diez-Barra E, De la Hoz A, Diaz-Ortiz A, Prieto P (1993) Synth Commun 23:1935
Diaz-Ortiz A, Prieto P, Loupy A, Abenhaïm D ( 1996) Tetrahedron Lett 37:1936
Loupy A, Luche JL (1997) In: Handbook of phase transfer catalysis, Chapman and Hall, London, chap 11, p 369
Sasson Y, Weiss M, Loupy A, Bram G, Pardo C (1986) J Chem Soc Chem Commun 1250
Loupy A, Pardo C (1988) Synth Commun 18:1275
Loupy A, Bram G, Sansoulet J, Vaziri-Zand F (1986) New J Chem 10:765
Oussaid A, Pentek E, Loupy A (1997) New J Chem 21:1339
Kornblum N, Seltzer R, Haberfield P ( 1963) J Am Chem Soc 85:1148
Matsumoto K (1980) Angew Chem 82:1046
Bram G, Sansoulet J, Galons H, Miocque M (1988) Synth Commun 18:367
Mirza-Aghayan M, Etemad-Moghadam G, Zaparucha A, Berlan J, Loupy A, Koenig M (1995) Tetrahedron: Asymmetry 6:2643
Loupy A, Sansoulet J, Zaparucha A, Mérienne C (1989) Tetrahedron Lett 30:333
Loupy A, Zaparucha A (1993) Tetrahedron Lett 34:473
Jones GB, Chapman BJ (1995) Synthesis 475
Conn RSE, Lovell AV, Karady S, Weinstock LM (1986) J Org Chem 51:4710
Diez-Barra E, De la Hoz A, Merino S, Sanchez-Verdu P (1997) Tetrahedron Lett 38: 2359
Diez-Barra E, De la Hoz A, Merino S, Sanchez-Verdu P (1997) In: Halpern ME (ed) Phase transfer catalysis, mechanism and syntheses. ACS Symposium Series 659, chap 14, p 181
Diez-Barra E, De la Hoz A, Merino S, Sanchez-Verdu P, Rodriguez A ( 1998) Tetrahedron 54:1835
Van Eldick R, Hubbard CD (1997) In: Chemistry under extreme or non-classical conditions, Wiley, New York
Loupy A (1993) Spectra Analyse 175:33
Abramovitch RA (1991) Org Prep Proc Int 23:685; Caddick S (1995) Tetrahedron 51:10403
Jullien SC, Delmotte M, Loupy A, Jullien H (1991) In: Microwaves and high frequencies, International Congress, Nice (France) 8–10 October, p 654
Stuerga D, Gaillard P ( 1996) Tetrahedron 52:5505
Lewis DA, Summers JD, Ward TC, Mc Grath JE (1992) J Polym Sci A 30:1647
Binner JGP,H assine NA, Cross TE (1995) J Mater Sci 30:5389
Gedye R, Smith F, Westaway K, Ali H, Baldisera L, Laberge L,R ousell J ( 1986) Tetrahedron Lett 27:279
Giguere RJ, Bray TL, Duncan SM, Majetich G (1986) Tetrahedron Lett 27:4945
Loupy A, Petit A, Hamelin J, Texier-Boullet F, Jacquault P, Mathé D ( 1998) Synthesis, 1213
Villemin D, Thibault-Starzyk F (1991) J Chem Educ 346
Jacquault P (1992) EU Patent 545995 AI Prolabo Co
Guttierez E, Loupy A, Bram G, Ruiz-Hitzky E (1989) Tetrahedron Lett 30:945
Trehan IR, Brar JS, Arora AK, Kad GL ( 1997) J Chem Educ 74:324
Singh J, Kaur J, Nayyar S, Kad GL ( 1998) J Chem Res S 280
Perez ER, Marrerro AL, Perez R, Autié MA (1995) Tetrahedron Lett 36:1779
Acosta A, De la Cruz P, De Miguel P, Diez-Barra A, De la Hoz A, Langa F, Loupy A, Majdoub M, Martin N, Sanchez C, Seoane C (1995) Tetrahedron Lett 36:2165
Csiba M, Cléophax J, Loupy A, Malthête J, Gero S ( 1993) Tetrahedron Lett 34:1787
Bram G, Loupy A, Majdoub M, Gutierrez E, Ruiz-Hitzky E ( 1990) Tetrahedron 46:5167
Van den Eynde JJ, Fromont D ( 1997) Bull Soc Chim Belg 106:393
Ranu BC, Saha M, Bhar S (1997) Synth Commun 27:621
Michaud D, Texier-Boullet F, Hamelin J (1997) Tetrahedron Lett 38:7563
Varma VS, Chatterjee AK, Varma M (1993) Tetrahedron Lett 34:4603
Varma VS, Lamture JB, Varma M (1993) Tetrahedron Lett 34:3029
Varma VS, Chatterjee AK, Varma M (1993) Tetrahedron Lett 34:3207
Oussaid A, Loupy A (1997) J Chem Res S 342
Benhaliliba H, Derchour A, Bazureau JP, Texier-Boullet F, Hamelin J (1998) Tetrahedron Lett 39:541
Suarez M, Loupy A, Perez E, Moran T, Gerona G, Morales A, Autié M (1996) Heterocyclic Commun 2:275
Cotterill IC, Usyatinsky AY, Arnold JM, Clark DS, Dordick JS, Michels PC, Khmelnitsky YL (1998) Tetrahedron Lett 39:1117
Villemin D, Ben Alloum A (1990) Synth Commun 20:3325
Villemin D, Ben Alloum A, Thibault-Starzyk (1992) Synth Commun 22:1359
Bougrin K, Soufiaoui M, Loupy A, Jacquault P ( 1995) New J Chem 19:213
Limousin C, Cléophax J, Petit A, Loupy A, Lukacs G (1997) J Carbohydr Res 16:327
Abenhaïm D, Loupy A, Mahieu C, Séméria D ( 1994) ) Synth Commun 24:1809
Jiang Y, Wang Y, Deng R, Mi A (1997) In: Halpern ME (ed) Phase transfer catalysis,mechanisms and syntheses. ACS Symposium Series 659, chap 16, p 203
Loupy A, Pigeon P, Ramdani M (1996) Tetrahedron 52:6705
Loupy A, Petit A, Ramdani M, Yvanaeff C, Majdoub M, Labiad B, Villemin D (1993) Can J Chem 71:90
Abenhaïm D, Loupy A, Ngoc Son CP, Nguyen Ba H ( 1994) Synth Commun 24:1199
Loupy A, Pigeon P, Ramdani M, Jacquault P ( 1994) Synth Commun 24:159
Lewis DA (1992) Mat Res Soc Symp Proc 269:21
Barnier JP, Loupy A, Pigeon P, Ramdani M, Jacquault P (1993) J Chem Soc Perkin Trans 1 397
Bogdal D, Pielichowski J, Boron A (1996) Synlett 873
Bogdal D, Pielichowski J, Jaskot K (1997) Heterocycles 45:715
Oussaid A, Le Ngoc T, Loupy A (1997) Tetrahedron Lett 38:2451
Diez-Barra E, Abenhaïm D, De la Hoz A, Loupy A, Sanchez-Migallon A (1994) Heterocycles 38:793
Jaisinghani HG, Khadilkar BM (1997) Tetrahedron Lett 39:6875
Borah HN, Boruah RC, Sandhu JS (1998) J Chem Res S 272
Loupy A, Petit A, Bonnet-Delpon D (1995) J Fluorine Chem 75:215
Boruah B, Prajapati D, Boruah A, Sandhu JS (1997) Synth Commun 27:2563
Diez-Barra E, De la Hoz A, Carrillo-Munoz JR, Diaz-Ortiz A, Gomez-Escalonilla MJ, Moreno A, Langa F (1996) Tetrahedron 52:9237
Bortolussi M, Bloch R, Loupy A (1998) J Chem Res S 34
Guibé-Jampel E, Rousseau G (1987) Tetrahedron Lett 28:3563
Carrillo-Munoz JR, Bouvet D, Guibé-Jampel E, Loupy A, Petit A (1996) J Org Chem 61:7746
Chemat F, Poux M, Berlan J ( 1994) J Chem Soc Perkin Trans 2 2597
Porcelli M, Cacciapuoti G, Fusco S, Massa R, d’Ambrosio G, Bertoldo C, De Rosa M, Zappia V (1997) FEBS Lett 402:102
Gelo-Pujic M, Guibé-Jampel E, Loupy A, Galema SA, Mathé D ( 1996) J Chem Soc Perkin Trans 1 2777
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Loupy, A. (1999). Solvent-free Reactions. In: Knochel, P. (eds) Modern Solvents in Organic Synthesis. Topics in Current Chemistry, vol 206. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48664-X_7
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