Phase Transfer Catalysis
Mieczysław Mąkosza,
Michał Fedoryński,
Mieczysław Mąkosza
Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland
Search for more papers by this authorMichał Fedoryński
Warsaw University of Technology, Warsaw, Poland
Search for more papers by this authorMieczysław Mąkosza,
Michał Fedoryński,
Mieczysław Mąkosza
Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland
Search for more papers by this authorMichał Fedoryński
Warsaw University of Technology, Warsaw, Poland
Search for more papers by this authorFirst published: 15 September 2010
Abstract
Basic concept of phase transfer catalysis (PTC), specific features of this general methodology for executing organic reactions, and mechanism of catalytic action of PT catalysts are presented. Scope and limitations of application of PTC as a general tool of organic synthesis and advantages offered by this methodology are discussed. These discussions are illustrated by numerous examples of successful use of PTC in a variety of reactions of inorganic anions (substitution and addition reactions, β-eliminations, oxidations, and reductions), heteroanions, and particularly carbanions (reactions with alkylating agents, carbonyl groups, activated carbon-carbon multiple bonds, electrophilic arenes, heteroatom electrophiles) and carbenes. Possibility of use of PTC for reactions of metalloorganic compounds and complexes and for enantioselective reactions is discussed.
Bibliography
- 1 C. M. Starks, C. L. Liotta, and M. Halpern, Phase-Transfer Catalysis, Fundamentals, Applications and Industrial Perspectives, Chapman & Hall, London, 1994.
- 2 E. V. Dehmlow and S. S. Dehmlow, Phase Transfer Catalysis, 3rd edn., VCH, Weinheim, 1993.
- 3
Y. Sasson and
R. Neumann, eds.,
Handbook of Phase Transfer Catalysis,
Blackie Academic & Professional,
London,
1997.
10.1007/978-94-009-0023-3 Google Scholar
- 4 Y. Goldberg, Phase Transfer Catalysis, Selected Problems and Applications, Gordon & Breach Science Publishers, New York, 1992.
- 5 R. A. Jones, Quaternary Ammonium Salts: Their Use in Phase-Transfer Catalysis, Academic Press, New York, 2001.
- 6 A. G. Volkov, ed., Interfacial Catalysis, Marcel Dekker, New York, 2003.
- 7(a) M. Mąkosza, Pure Appl. Chem. 43, 439 (1975); (b) M. Mąkosza and M. Fedoryński, Adv. Catal. 35, 375 (1987); (c) M. Mąkosza and M. Fedoryński, Polish J. Chem. 70, 1093 (1996); (d) M. Mąkosza and M. Fedoryński, Cat. Revs. 45, 321 (2003).
- 8 W. E. Keller, Phase-Transfer Reactions, Fluka Compendium, Georg Thieme Verlag, Stuttgart, New York, Vol. I, 1986; Vol. II, 1987; Vol. III, 1992.
- 9 M. T. Khanh, T. K. Qui, N. T. Hong, and A. Loupy, Synth. Commun. 26, 1305 (1996).
- 10 B. K. Wilk, N. Mwisiya, and J. L. Helom, Org. Proc. Res. Dev. 12, 785 (2008).
- 11 W. Lasek and M. Mąkosza, Synthesis 780 (1993).
- 12 S. Baj, A. Siewniak, and B. Socha, Appl. Catal. A: General 309, 85 (2006).
- 13 D. Seebach, H.-O. Kalinowski, W. Langer, G. Crass, and E.-M. Wilka, Org. Synth. Coll. 7, 41 (1990).
- 14 M. Penso, V. Lupi, D. Albanese, F. Foschi, D. Landini, and A. Tagliabue, Synlett 2451 (2008).
- 15 F. Faltin, V. Fehring, and R. Miethchen, Synthesis 1851 (2002).
- 16 M. Penso, D. Albanese, D. Landini, V. Lupi, and A. Tagliabue, J. Org. Chem. 73, 6686 (2008).
- 17 K. Osowska-Pacewicka and A. Zwierzak, Synthesis 333 (1996).
- 18 A. Khalafi-Nezhad, M. N. Soltani Rad, H. Mohabatkar, Z. Asrari, and B. Hemmateenejad, Bioorg. Med. Chem. 13, 1931 (2005).
- 19 S. Voskresensky and M. Mąkosza, Synth. Commun. 30, 3523 (2000).
- 20 D. Landini and F. Rolla, Org. Synth. Coll. 6, 833 (1988).
- 21 M. Mąkosza and A. Jończyk, Org. Synth. Coll. 6, 897 (1988).
- 22 M. Mąkosza and A. Chesnokov, Tetrahedron 64, 5925 (2008).
- 23 M. Barbasiewicz, K. Marciniak, and M. Fedoryński, Tetrahedron Lett. 47, 3871 (2006).
- 24 T. Norris and K. Leeman, Org. Proc. Res. Dev. 12, 869 (2008).
- 25 I. L. Odinets, O. I. Artyushin, S. V. Lenevich, G. V. Bodrin, K. A. Lyssenko, I. V. Fedyanin, P. V. Petrovskii, and T. A. Mastryukova, Russ. Chem. Bull. 53, 219 (2004).
- 26 G. P. Stahly, J. Fluorine Chem. 43, 53 (1989).
- 27 M. Mąkosza, J. Przyborowski, R. Klajn, and A. Kwast, Synlett 1773 (2000).
- 28 N. Niphade, A. Mali, K. Jagtap, R. Chandra Ojha, P. J. Vankawala, and V. T. Mathad, Org. Proc. Res. Dev. 12, 731 (2008).
- 29 G. V. Kryshtal, G. M. Zhdankina, and E. P. Serebryakov, Zh. Org. Khim. 30, 732 (1994); Chem. Abstr. 122, 132686a (1995).
- 30 T. Zdrojewski, M. Fedoryński, and A. Jończyk, Polish J. Chem. 71, 941 (1997).
- 31 E. V. Dehmlow and J. Kinnius, J. Prakt. Chem. 337, 153 (1995).
- 32(a) M. Mąkosza and M. Sypniewski, Tetrahedron Lett. 35, 6141 (1994); (b) Tetrahedron 51, 10593 (1995).
- 33 A. Pascariu, G. Ilia, A. Bora, A. Bora, S. Iliescu, A. Popa, G. Dehelean, and L. Pacureanu, Centr. Eur. J. Chem. 1, 491 (2003).
- 34 X. Zhang, P. Zhong, and F. Chen, Synth. Commun. 34, 1729 (2004).
- 35 G. V. Kryshtal, E. P. Serebryakov, L. M. Suslova, and L. A. Yanovskaya, Izv. Akad. Nauk SSSR, ser. Khim. 1417 (1990); Chem. Abstr. 113, 211355j (1990).
- 36 K. Popandova-Yambolieva, Synth. Commun. 20, 1857 (1990).
- 37 A.-H. Li, L.-X. Dai, and X.-L. Hou, J. Chem. Soc., Chem. Commun. 491 (1996).
- 38 M. Shostakovsky and R. M. Carlson, Synth. Commun. 26, 1785 (1996).
- 39 A. Jończyk and A. Konarska, Synlett 1085 (1999).
- 40 H. Wang, Y. Chen, W. Cao, H. Ding, J. Chen, H. Deng, and M. Shao, Synthesis 3995 (2008).
- 41 M. Mąkosza, J. Czyżewski, and M. Jawdosiuk, Org. Synth. Coll. 6, 940 (1988).
- 42 A. Jończyk, T. Kuliński, M. Czupryniak, and P. Balcerzak, Synlett 639 (1991).
- 43 E. N. Durantini, S. M. Chiacchiera, and J. J. Silber, Synth. Commun. 26, 3849 (1996).
- 44 S. Varela Calafat, E. N. Durantini, S. M. Chiacchiera, and J. J. Silber, J. Org. Chem. 70, 4659 (2005).
- 45 E. Abele and E. Lukevics, Org. Prep. Proc. Int. 31, 359 (1999).
- 46 H. J. Ledon, Org. Synth. Coll. 6, 414 (1988).
- 47 P. Balcerzak and A. Jończyk, J. Chem. Res. (S) 200 (1994).
- 48 J. Matsuo, Y. Tani, and Y. Hayakawa, Chem. Lett. 33, 464 (2004).
- 49 K. R. Mondanaro Lynch and W. P. Dailey, Org. Synth. Coll. 10, 658 (2004).
- 50 M. S. Baird, V. M. Boitsov, A. V. Stepakov, A. P. Molchanov, J. Kopf, M. Rajaratnam, and R. R. Kostikov, Tetrahedron 63, 7717 (2007).
- 51 A. Corsaro, M. A. Chiacchio, V. Pistara, A. Rescifina, and E. Vittorino, Tetrahedron 64, 8652 (2008).
- 52 M. G. Banwell, J. E. Harvey, D. C. R. Hockless, and A. W. Wu, J. Org. Chem. 65, 4241 (2000).
- 53 O. H. Kvernenes and L. K. Sydnes, Org. Synth. 83, 184 (2006).
- 54 A. C. Bissember, A. T. Phillis, M. G. Banwell, and A. C. Willis, Org. Lett. 9, 5421 (2007).
- 55 M. Fedoryński, Chem. Rev. 103, 1099 (2003).
- 56 M. G. Banwell, D. A. S. Beck, P. C. Stanislawski, M. O. Sydnes, and R. M. Taylor, Curr. Org. Chem. 9, 1589 (2005).
- 57 M. G. Banwell, Pure Appl. Chem. 80, 669 (2008).
- 58 G. W. Gokel, R. P. Widera, and W. P. Weber, Org. Synth. Coll. 6, 232 (1988).
- 59 E. Yu. Shinkevich, K. Abbaspour Tehrani, A. F. Khlebnikov, and M. S. Novikov, Tetrahedron 64, 7524 (2008).
- 60 K. Schank, A.-M. A. Abdel Wahab, S. Bügler, P. Eigen, J. Jager, and K. Jost, Tetrahedron 50, 3721 (1994).
- 61 K. N. Shavrin, I. V. Krylova, I. B. Shvedova, G. P. Okonnishnikova, I. E. Dolgy, and O. M. Nefedov, J. Chem. Soc., Perkin Trans. 2, 1875 (1991).
- 62 K. N. Shavrin, V. D. Gvozdev, and O. M. Nefedov, Izv. Akad. Nauk, ser. Khim. 1997, 2079; Russ. Chem. Bull. 46, 1973 (1997) (Engl. Ed.:).
- 63 A. Jończyk, H. Karwowska, and J. Furman, Synth. Commun. 36, 3571 (2006).
- 64 T. Jackson, L. W. Lawrence Woo, M. N. Trusselle, S. K. Chander, A. Purohit, M. J. Reed, and B. V. L. Potter, Org. Biomol. Chem. 5, 2940 (2007).
- 65 G. D. Yadav and J. L. Caesar, J. Mol. Cat. A: Chem. 260, 202 (2006).
- 66 N. F. Santos-Sanchez, R. Salas-Coronado, R. Colorado-Peralta, A. Pena-Hueso, S. A. Sanchez-Ruiz, and A. Flores-Parra, Arkivoc 2008 ( v), 187.
- 67 S. Kotha, P. Khedkar, and A. K. Ghosh, Eur. J. Org. Chem. 2005, 3581.
- 68 M. Mąkosza and R. Bujok, Tetrahedron Lett. 43, 276 (2002).
- 69 M. Mąkosza and R. Bujok, Tetrahedron Lett. 45, 1385 (2004).
- 70 V. Singh, R. Pathak, and S. Batra, Catal. Commun. 8, 2048 (2007).
- 71 M. Mąkosza and A. Chesnokov, Tetrahedron 56, 3553 (2000).
- 72 A. Jończyk, T. Koćmierowski, and T. Zdrojewski, New. J. Chem. 27, 295 (2003).
- 73(a) L. K. Sydnes, B. Holmelid, O. H. Kvernenes, M. Sandberg, M. Hodne, and E. Bakstad, Tetrahedron 63, 4144 (2007); (b) B. Holmelid, O. H. Kvernenes, M. Hodne, and L. K. Sydnes, Arkivoc ( vi), 26 (2008).
- 74
X. Liang-heng and
H. Nai-ju,
Synth. Commun.
20,
1563
(1990).
10.1080/00397919008052874 Google Scholar
- 75 M. S. Baird, P. Licence, V. V. Tverezovsky, I. G. Bolesov, and W. Clegg, Tetrahedron 55, 2773 (1999).
- 76 M. Menand, J. C. Blais, L. Hamon, J. M. Valery, and J. Xie, J. Org. Chem. 70, 4423 (2005).
- 77 D. G. Lee, S. E. Lamb, and V. S. Chang, Org. Synth. Coll. 7, 397 (1990).
- 78 V. A. Petrov, W. J. Marshall, C. G. Krespan, V. F. Cherstkov, and E. A. Avetisian, J. Fluorine Chem. 125, 99 (2004).
- 79 S. Schrader and E. V. Dehmlow, Org. Prep. Proc. Int. 32, 123 (2000).
- 80 W. Zhao, B. Ma, H. Hua, Y. Zhang, and Y. Ding, Catal. Commun. 9, 2455 (2008).
- 81 K. Sato, M. Aoki, J. Takagi, and R. Noyori, J. Am. Chem. Soc. 119, 12386 (1997).
- 82 K. Sato, M. Aoki, J. Takagi, and R. Noyori, Tetrahedron Lett. 39, 7549 (1998).
- 83 L. Cassar, Ann. N. Y. Acad. Sci. 333, 208 (1980).
- 84 H. Alper, Adv. Organomet. Chem. 19, 183 (1981).
- 85 H. Alper, Fundam. Res. Homogeneous Catal. 4, 79 (1984).
- 86 E. V. Dehmlow, in B. Cornils and W. A. Herrmann, eds., Aqueous-Phase Organometallic Catalysis, Concepts and Applications, 2nd ed., Wiley-VCH, Weinheim, Germany, 2004, Chapt. 4.6.1.
- 87 R. F. Wu, I. J. B. Lin, G. H. Lee, M. C. Cheng, and Y. Wang, Organometallics 9, 126 (1990).
- 88 H. des Abbayes, J.-C. Clement, P. Laurent, J.-J. Yaouanc, G. Tanguy, and B. Weinberger, J. Organometal. Chem. 359, 205 (1989).
- 89 S. R. Amin and A. Sarkar, Organometallics 14, 547 (1995).
- 90 I. Amer and H. Alper, J. Organometal. Chem. 383, 573 (1990).
- 91 T. Tu, W. Assenmacher, H. Peterlik, G. Schnakenburg, and K. H. Dötz, Angew. Chem., Int. Ed. 47, 7127 (2008).
- 92 B. Łęska, R. Pankiewicz, B. Gierczyk, and G. Schroeder, J. Mol. Catal;. A: Chem. 287, 165 (2008).
- 93U.S. Pat. 5132423 (1992), D. J. Brunelle, D. A. Haitko, J. P. Barren, and S. Singh.
- 94 G. Pozzi, S. Quici, and R. H. Fish, J. Fluorine Chem. 129, 920 (2008).
- 95(a) C. S. Consorti, M. Jurisch, and J. A. Gladysz, Org. Lett. 9, 2309 (2007); (b) D. Mandal, M. Jurisch, C. S. Consorti, and J. A. Gladysz, Chem. Asian J. 3, 1772 (2008).
- 96 D. Bogdal and A. Loupy, Org. Proc. Res. Dev. 12, 710 (2008).
- 97 M. Fedoryński, W. Ziółkowska, and A. Jończyk, J. Org. Chem. 58, 6120 (1993).
- 98 M. Fedoryński, Tetrahedron 55, 6329 (1999).
- 99 M. N. Masuno, D. M. Young, A. C. Hoepker, C. K. Skepker, and T. F. Molinski, J. Org. Chem. 70, 4162 (2005).
- 100 E. V. Dehmlow and S. Schrader, Z. Naturforsch. b 45, 409 (1990).
- 101 M. Fedoryński, M. Kubicka-Prusik, M. Kursa, and A. Jończyk, Tetrahedron 53, 1053 (1997).
- 102 E. V. Dehmlow, in M. E. Halpern, ed., Phase-Transfer Catalysis, Mechanisms and Syntheses, ACS Symposium Series 659, American Chemical Society, Washington, D.C., 1997, Chapt. 9, pp. 108–122.
- 103 E. V. Dehmlow, Russ. Chem. Bull., Engl. Ed. 44, 1998 (1995).
- 104(a) M. J. O'Donnell, Aldrichim. Acta 34, 3 (2001); (b) K. Kacprzak and J. Gawroński, Synthesis 2001, 961; (c) K. Maruoka, Proc. Japan Acad., Ser. B 79, 181 (2003); (d) M. J. O'Donnell, Acc. Chem. Res. 37, 506 (2004); (e) B. Lygo and B. I. Andrews, Acc. Chem. Res. 37, 518 (2004); (f) T. Ooi and K. Maruoka, Angew. Chem., Int. Ed. 46, 4222 (2007); (g) T. Hashimoto and K. Maruoka, Chem. Rev. 107, 5656 (2007); (h) T. Ooi and K. Maruoka, Aldrichim. Acta 40, 77 (2007); (k) K. Maruoka, Org. Proc. Res. Dev. 12, 679 (2008).
- 105 D. Dies, M. G. Nunez, A. B. Anton, P. Garcia, R. F. Moro, N. M. Garrido, I. S. Marcos, P. Basabe, and J. G. Urones, Curr. Org. Synth. 5, 186 (2008).
- 106 K. Maruoka, ed., Asymmetric Phase Transfer Catalysis, Wiley-VCH, Weinheim,Germany, 2008.
- 107 E. J. Corey and M. C. Noe, Org. Synth. 80, 38 (2003).
- 108 M. Kitamura, Y. Arimura, S. Shirakawa, and K. Maruoka, Tetrahedron Lett. 49, 2026 (2008).
- 109 T. Kano, Q. Lan, X. Wang, and K. Maruoka, Adv. Synth. Catal. 349, 556 (2007).
- 110 J. P. Scott, M. S. Ashwood, K. M. J. Brands, S. E. Brewer, C. J. Cowden, U.-H. Dolling, K. M. Emerson, A. D. Gibb, A. Goodyear, S. F. Oliver, G. W. Stewart, and D. J. Wallace, Org. Proc. Res. Dev. 12, 723 (2008).
- 111 X. Jiang, B. Gong, K. Prasad, and O. Repic, Org. Proc. Res. Dev. 12, 1164 (2008).
- 112 M. Nakoji, T. Kanayama, T. Okino, and Y. Takemoto, Org. Lett. 3, 3329 (2001).
- 113 M. Mąkosza, Pure Appl. Chem., 72, 1399 (2000).
