Conclusion - Heterogeneous Reactions - Microreactors in Organic Chemistry and Catalysis, Second Edition (2013)

Microreactors in Organic Chemistry and Catalysis, Second Edition (2013)

7. Heterogeneous Reactions

7.10. Conclusion

Recent years have seen enormous advances in the field of continuous flow reactions in combination with heterogeneous reagents or catalysts. The processes offer many synthetic advantages with respect to efficiency, safety, and environmental benignancy as well as reliable quality control of the products. In addition, since the solid phase is easy to remove from the reaction mixture, multi-step synthetic systems can be designed under continuous flow conditions without traditional purification and work-up processes. The heterogeneous flow systems can be in line attached with additional components, such as a hydrogen generator, recirculating system, a homogeneous microreactor, a solid-supported scavenger column, a microwave irradiator, an analytical spectrometer, a microextractor, and so on.

Although all studies of the heterogeneous flow processes cannot be covered in this chapter due to the limited pages, the number of examples is still small today. Further studies and challenges with new innovation may guide to next generation of ideal synthetic methodologies.

References

1. Mason, B.P., Price, K.E., Steinbacher, J.L., Bogdan, A.R., and McQuade, D.T. (2007) Chem. Rev., 107, 2300–2318.

2. Razzaq, T. and Kappe, C.O. (2010) Chem. Asian J., 5, 1274–1289.

3. Wegner, J., Ceylan, S., and Kirschning, A. (2011) Chem. Commun., 47, 4583–4592.

4. Rasheed, M. and Wirth, T. (2011) Angew. Chem., Int. Ed., 50, 357–358.

5. Hartman, R.L., McMullen, J.P., and Jensen, K.F. (2011) Angew. Chem., Int. Ed., 50, 7502–7519.

6. Malet-Sanz, L. and Susanne, F. (2012) J. Med. Chem., 55, 4062–4098.

7. Wiles, C. and Watts, P. (2012) Green Chem., 14, 38–54.

8. Merrifield, R.B. (1963) J. Am. Chem. Soc., 85, 2149–2154.

9. Ley, S.V., Baxendale, I.R., Bream, R.N., Jackson, A.G., Leach, A.G., Longbottom, D.A., Nesi, M., Scott, R.I., Storer, R.I., and Taylor, S.J. (2000) J. Chem. Soc., Perkin Trans. 1, 3815–4195.

10. Kirschning, A., Monenschein, H., and Wittenberg, R. (2001) Angew. Chem., Int. Ed., 40, 650–679.

11. Gladysz, J.A. (2002) Chem. Rev., 102, 3215–3216.

12. McNamara, C.A., Dixon, M.J., and Bradley, M. (2002) Chem. Rev., 102, 3275–3300.

13. Kirschning, A., Solodenko, W., and Mannecke, K. (2006) Chem. Eur. J., 12, 5972–5990.

14. Frost, C.G. and Mutton, L. (2010) Green Chem., 12, 1687–1703.

15. Baumann, M., Baxendale, I.R., and Ley, S.V. (2011) Mol. Divers., 15, 613–630.

16. Yoshida, J.-i., Saito, K., Nokami, T., and Nagaki, A. (2011) Synlett, 1189–1194.

17. Dudukoviimg, M.P., Larachi, F., and Mills, P.L. (2002) Catal. Rev., 44, 123–246.

18. Hodge, P. (2003) Curr. Opin. Chem. Biol., 7, 362–373.

19. Sachse, A., Galarneau, A., Coq, B., and Fajula, F. (2011) New J. Chem., 35, 259–264.

20. Jas, G. and Kirschning, A. (2003) Chem. Eur. J., 9, 5708–5723.

21. Svec, F. and Fréchet, J.M.J. (1996) Science, 273, 205–211.

22. Peters, E.C., Svec, F., and Fréchet, J.M.J. (1999) Adv. Mater., 11, 1169–1181.

23. Kiwi-Minsker, L. (2002) Chimia, 56, 143–147.

24. Svec, F. and Fréchet, J.M.J. (1992) Anal. Chem., 64, 820–822.

25. Altava, B., Burguete, M.I., Fraile, J.M., García, J.I., Luis, S.V., Mayoral, J.A., and Vincent, M.J. (2000) Angew. Chem., Int. Ed., 39, 1503–1506.

26. Tripp, J.A., Stein, J.A., Svec, F., and Fréchet, J.M.J. (2002) Org. Lett., 2, 195–198.

27. Zalusky, S., Olayo-Valles, R., Taylor, C.J., and Hillmyer, M.A. (2001) J. Am. Chem. Soc., 123, 1519–1520.

28. Hornung, C.H., Mackley, M., Baxendale, I.R., and Ley, S.V. (2007) Org. Process Res. Dev., 11, 399–405.

29. Hornung, C.H., Hallmark, B., Mackley, M.R., Baxendale, I.R., and Ley, S.V. (2010) Adv. Synth. Catal., 352, 1736–1745.

30. Shore, G., Yoo, W.J., Li, C.-J., and Organ, M.G. (2009) Chem. Eur. J., 17, 1884–1893.

31. Ceylan, S., Friese, C., Lammel, C., Mazac, K., and Kirschning, A. (2008) Angew. Chem., Int. Ed., 47, 8950–8953.

32. Ceylan, S., Coutable, L., Wegner, J., and Kirschning, A. (2011) Chem. Eur. J., 16, 126–133.

33. Uozumi, Y., Yamada, Y.M.A., Beppu, T., Fukuyama, N., Ueno, M., and Kitamori, T. (2006) J. Am. Chem. Soc., 128, 15994–15995.

34. Yamada, Y.M.A., Watanabe, T., Torii, K., and Uozumi, Y. (2009) Chem. Commun., 5594–5596.

35. Yamada, Y.M.A., Watanabe, T., Ohno, A., and Uozumi, Y. (2012) ChemSusChem, 5, 293–299.

36. Harrison, C.R. and Hodge, P. (1976) J. Chem. Soc., Perkin Trans. 1, 2252–2254.

37. Harrison, C.R. and Hodge, P. (1982) J. Chem. Soc., Perkin Trans. 1, 509–511.

38. Jönsson, D., Warrington, B.H., and Ladlow, M. (2004) J. Comb. Chem., 6, 584–595.

39. Griffiths-Jones, C.M., Hopkin, M.D., Jonsson, D., Ley, S.V., Tapolczay, D.J., Vickerstaffe, E., and Ladlow, M. (2007) J. Comb. Chem., 9, 422–430.

40. Wiles, C., Watts, P., and Haswell, S.J. (2006) Tetrahedron Lett., 47, 5261–5264.

41. Itsuno, S., Ito, K., Maruyama, T., Kanda, N., Hirao, A., and Nakahama, S. (1986) Bull. Chem. Soc. Jpn., 59, 3329–3331.

42. Noël, T., Maimone, T.J., and Buchwald, S.L. (2011) Angew. Chem., Int. Ed., 50, 8900–8903.

43. Wild, G.P., Wiles, C., Watts, P., and Haswell, S.J. (2009) Tetrahedron, 65, 1618–1629.

44. Curran, D.P. (1998) Angew. Chem., Int. Ed., 37, 1174–1196.

45. Yoshida, J.-I. and Itami, K. (2002) Chem. Rev., 102, 3693–3716.

46. Kirschning, A., Altwicker, C.G., Dräger, G., Harders, J., Hoffmann, N., Hoffmann, U., Schönfeld, H., Solodenko, W., and Kunz, U. (2001) Angew. Chem., Int. Ed., 40, 3995–3998.

47. Solodenko, W., Kunz, U., Jas, G., and Kirschning, A. (2002) Bioorg. Med. Chem. Lett., 12, 1833–1835.

48. Solodenko, W., Wen, H., Leue, S., Stuhlmann, F., Sourkouni-Argirusi, G., Jas, G., Schönfeld, H., Kunz, U., and Kirschning, A. (2004) Eur. J. Org. Chem., 3601–3610.

49. Kunz, U., Schönfeld, H., Solodenko, W., Jas, G., and Kirschning, A. (2005) Ind. Eng. Chem. Res., 44, 8458–8467.

50. Kupracz, L., Hartwig, J., Wegner, J., Ceylan, S., and Kirschning, A. (2011) Beilstein J. Org. Chem., 7, 1441–1448.

51. Baumann, M., Baxendale, I.R., Ley, S.V., Nikbin, N., and Smith, C.D. (2008) Org. Biomol. Chem., 6, 1587–1593.

52. Smith, C.J., Smith, C.D., Nikbin, N., Ley, S.V., and Baxendale, I.R. (2011) Org. Biomol. Chem., 9, 1927–1937.

53. Roper, K.A., Lange, H., Polyzos, A., Berry, M.B., Baxendale, I.R., and Ley, S.V. (2011) Beilstein J. Org. Chem., 7, 1648–1655.

54. Lange, H., Capener, M.J., Jones, A.X., Smith, C.J., Nikbin, N., Baxendale, I.R., and Ley, S.V. (2011) Synlett, 869–873.

55. Karnats, F.A. and Whitmore, F.C. (1932) J. Am. Chem. Soc., 54, 3461.

56. Rueping, M., Bootwicha, T., Baars, H., and Sugiono, E. (2011) Beilstein J. Org. Chem., 7, 1680–1687.

57. Abahmane, L., Knauer, A., Ritter, U., Köhler, J.M., and Groß, G.A. (2009) Chem. Eng. Technol., 32, 1799–1805.

58. Irfan, M., Glasnov, T.N., and Kappe, C.O. (2011) ChemSusChem, 4, 300–316.

59. Chinnusamy, T., Yudha, S.S., Hager, M., Kreitmeier, P., and Reiser, O. (2012) ChemSusChem, 5, 247–255.

60. http://www.thalesnano.com/products/h-cube (accessed 15 November 2012).

61. Jones, R.V., Gödörházy, L., Szalay, D., Gerencsér, J., Dormán, G., Ürge, L., and Darvas, F. (2005) QSAR Comb. Sci., 24, 722–727.

62. Jones, R.V., Gödörházy, L., Varga, N., Szalay, D., Ürge, L., and Darvas, F. (2006) J. Comb. Chem., 8, 110–116.

63. Niesz, K., Hornyak, I., Borcsek, B., and Darvas, F. (2008) Microfluidics Nanofluidics., 5, 411–416.

64. Irfan, M., Petricci, E., Glasnov, T.N., Taddei, M., and Kappe, C.O. (2009) Eur. J. Org. Chem., 1327–1334.

65. Low, S., Dai, P., and Schaus, S.E. (2007) J. Org. Chem., 72, 9998–10008.

66. Saaby, S., Ladlow, M., and Ley, S.V. (2005) Chem. Commun., 2909–2911.

67. Franckevicius, V., Knudsen, K., Ladlow, M., Longbottom, D.A., and Ley, S.V. (2006) Synlett, 889–892.

68. Horvath, H.H., Papp, G., Csajagi, C., and Joo, F. (2007) Catal. Commun., 8, 442–446.

69. Knudsen, K.R., Holden, J., Ley, S.V., and Ladlow, M. (2007) Adv. Synth. Catal., 349, 535–538.

70. Baumann, M., Baxendale, I.R., and Ley, S.V. (2010) Synlett, 749–752.

71. Bagwell, C.L., Moloney, M.G., and Yaqoob, N. (2010) Bioorg. Med. Chem. Lett., 20, 2090–2094.

72. Jones, A.L. and Snyder, J.K. (2010) Org. Lett., 12, 1592–1595.

73. Taeleton, M. and McCluskey, A. (2011) Tetrahedron Lett., 52, 1583–1586.

74. Bryan, M.C., Wernick, D., Hein, C.D., Peterson, J.V., Eshelbach, J.A., and Doherty, E.M. (2011) Beilstein J. Org. Chem., 7, 1141–1159.

75. Taeleton, M., Young, K.A., Unicomb, E., McCluskey, S.N., Robartson, M.J., Gordon, C., and McCluskey, A. (2011) Lett. Drug Des. Discov., 8, 568–574.

76. Colombo, E., Ratel, P., Mounier, L., and Guillier, F. (2011) J. Flow Chem., 2, 68–73.

77. Cooper, C.G.F., Lee, E.R., Silva, R.A., Bourque, A.J., Clark, S., Katti, S., and Nivororozhkin, V. (2012) Org. Process Res. Dev., 16, 1090–1097.

78. Yoswathananont, N., Nitta, K., Nishiuchi, Y., and Sato, M. (2005) Chem. Commun., 40–42.

79. Lessard, J., Morin, J.F., Wehrung, J.F., Magnin, D., and Chornet, E. (2010) Top. Catal., 53, 1231–1234.

80. Fan, X., Liu, S., Yan, X., Du, X., and Chen, L. (2010) Catal. Commun., 11, 960–963.

81. Szöllösi, G., Hermán, B., Fülöp, F., and Bartók, M. (2006) React. Kinet. Catal. L., 88, 391–398.

82. Szöllösi, G., Cserenyl, S., Fülöp, F., and Bartók, M. (2008) J. Catal., 260, 245–253.

83. Madarász, J., Farkas, G., Balogh, S., Szöllósy, Á., Kovács, J., Darvas, F., Ürge, L., and Bakos, J. (2011) J. Flow Chem., 2, 62–67.

84. Balogh, S., Farkas, G., Madarász, J., Szöllösy, Á., Kovács, J., Darvas, F., Ürge, L., and Bakos, J. (2012) Green Chem., 14, 1146–1151.

85. Kunz, U., Kirschning, A., Wen, H.-L., Solodenko, W., Cecilia, R., Kappe, C.O., and Turek, T. (2005) Catal. Today, 105, 318–324.

86. Kunz, U., Schonfeld, H., Kirschning, A., and Solodenko, W. (2003) J. Chromatogr. A, 1006, 241–249.

87. Kobayashi, J., Mori, Y., and Kobayashi, S. (2006) Chem. Asian J., 1–2, 22–35.

88. Kobayashi, J., Mori, Y., Okamoto, K., Akiyama, R., Ueno, M., Kitamori, T., and Kobayashi, S. (2004) Science, 304, 1305–1308.

89. Kobayashi, J., Mori, Y., and Kobayashi, S. (2005) Chem. Commun., 2567–2568.

90. Bakker, J.J.W., Zieverink, M.M.P., Reintjens, R.W.E.G., Kapteijn, F., Moulijin, J.A., and Kerutzer, M.T. (2011) ChemCatChem, 3, 1155–1157.

91. Noël, T. and Buchwald, S.L. (2011) Chem. Soc. Rev., 40, 5010–5029.

92. Glasnov, T.N., Findenig, S., and Kappe, C.O. (2009) Chem. Eur. J., 15, 1001–1010.

93. De Vries, A.H., Mulders, J.M.C.A., Mommers, J.H.M., Henderickx, H.J.W., and De Vries, J.G. (2003) Org. Lett., 5, 3285–3288.

94. Nikbin, N., Ladlow, M., and Ley, S.V. (2007) Org. Process Res. Dev., 11, 458–462.

95. Sigma-Aldrich, QuadrapureTU, is a thiourea-based scavenger with high affinity to metal, ions. Available at http://www.sigmaaldrich.com (accessed 15 November 2012).

96. Brown, J.F., Krajnc, P., and Cameron, N.R. (2005) Ind. Eng. Chem. Res., 44, 8565–8572.

97. Mennecke, K., Solodenko, W., and Kirschning, A. (2008) Synthesis, 1589–1599.

98. Nasielski, J., Hadei, N., Achonduh, G., Kantchev, E.A.B., O'Brien, C.J., Lough, A., and Organ, G. (2010) Chem. Eur. J., 16, 10844–10853.

99. Mennecke, K. and Kirschning, A. (2008) Synthesis, 3267–3272.

100. Naber, J.R. and Buchwald, S.L. (2010) Angew. Chem., Int. Ed., 49, 9469–9474.

101. Csajági, C., Borcsek, B., Niesz, K., Kovács, I., Székelyhidi, Z., Bajkó, Z., Ürge, L., and Darvas, F. (2008) Org. Lett., 10, 1589–1592.

102. Balogh, J., Kuik, Á., Ürge, L., Darvas, F., Bakos, J., and Skoda-Földes, R. (2009) J. Mol. Catal. A: Chem., 302, 76–79.

103. Noël, T. and Musacchio, A.J. (2011) Org. Lett., 13, 5180–5183.

104. Yang, G.R., Bae, G., Choe, J., Lee, S., and Song, K.H. (2010) Bull. Korean Chem. Soc., 31, 250–252.

105. Zhang, Y., Jamison, T.F., Patel, S., and Mainolfi, N. (2011) Org. Lett., 13, 280–283.

106. He, P., Haswell, S.J., and Fletcher, P.D.I. (2004) Appl. Catal. A: Gen., 274, 111–114.

107. Shore, G., Morin, S., and Organ, M.G. (2006) Angew. Chem., Int. Ed., 45, 2761–2766.

108. Ramarao, C., Ley, S.V., Smith, S.C., Shirley, I.M., and DeAlmeida, N. (2002) Chem. Commun., 1132–1133.

109. Baxendale, I.R., Griffiths-Jones, C.M., Ley, S.V., and Tranmer, G.K. (2006) Chem. Eur. J., 12, 4407–4416.

110. Baxendale, I.R., Deeley, J., Griffiths-Jones, C.M., Ley, S.V., and Tranmer, G.K. (2006) Chem. Commun., 2566–2568.

111. Kobayashi, S., Miyamura, H., Akiyama, R., and Ishida, T. (2005) J. Am. Chem. Soc., 127, 9251–9254.

112. Derikvand, F., Bigi, F., Maggi, R., Piscopo, C.G., and Sartoni, G. (2010) J. Catal., 271, 99–103.

113. Zotova, N., Hellgradt, K., Kelsall, G.H., Jassiman, A.S., and Hii, K.K.M. (2010) Green Chem., 12, 2157–2163.

114. Fuchs, M., Goessler, M., Pilger, C., and Kappe, C.O. (2010) Adv. Synth. Catal., 352, 323–328.

115. Ceylan, S., Klande, T., Vogt, C., Friese, C., and Kirschning, A. (2010) Synlett, 2009–2013.

116. Shore, G., Tsimerman, M., and Organ, M.G. (2009) Beilstein J. Org. Chem., 5, No. 35.

117. Mak, X.Y., Laurino, P., and Seeberger, P.H. (2009) Beilstein J. Org. Chem., 5, No. 19.

118. Murguete, M.I., García-Verdugo, E., Vicent, M.J., Luis, S.V., Pennemann, H., von Keyserling, N.G., and Martens, J. (2002) Org. Lett., 4, 3947–3950.

119. Hodge, P., Sung, D.W., and Stratford, P. (1999) J. Chem. Soc., Perkin Trans. 1, 2335–2342.

120. Pericàs, M.A., Herrerías, C.I., and Solà, L. (2008) Adv. Synth. Catal., 350, 927–932.

121. Osoria-Planes, L., Rodríguez-Escrich, C., and Pericàs, M.A. (2012) Org. Lett., 14, 1816–1819.

122. Rolland, J., Cambeiro, X.C., Rodríguez-Escrich, C., and Pericàs, M.A. (2009) Beilstein J. Org. Chem., 5, No. 56.

123. Seayad, A.M., Ramalingam, B., Yoshinaga, K., Nagata, T., and Chai, C.L.L. (2010) Org. Lett., 12, 264–267.

124. Seayad, A.M., Ramalingam, B., Chai, C.L.L., Li, C., Garland, M.V., and Yoshinaga, K. (2012) Chem. Eur. J., 18, 5693–5700.

125. Mandoli, A., Orlandi, S., Pini, D., and Salvador, P. (2004) Tetrahedron: Asymmetry, 15, 3233–3244.

126. Kamahori, K., Ito, K., and Itsuno, S. (1996) J. Org. Chem., 61, 8321–8324.

127. Annis, D.A. and Jacobsen, E.N. (1999) J. Am. Chem. Soc., 121, 4147–4154.

128. Solodenko, W., Jas, G., Kunz, U., and Kirschning, A. (2007) Synthesis, 583–589.

129. Baquey, G., Alvès, M.-H., Graullier, M., Riondel, A., Paul, J.-M., Birot, M., and Deleuze, H. (2009) Green Chem., 11, 868–872.

130. Phan, N.T.S., Khan, J., and Styring, P. (2005) Tetrahedron, 61, 12065–12073.

131. Haswell, S.J., O'Sullivan, B., and Styring, P. (2001) Lab Chip, 1, 164–166.

132. Phan, N.T.S., Brown, D.H., and Styring, P. (2004) Green Chem., 6, 526–532.

133. Beiji, M., Haag, R., and Liese, A. (2008) Adv. Synth. Catal., 350, 919–925.

134. Krause, J.O., Lubbad, S.H., Nuyken, O., and Buchmeiser, M.R. (2003) Macromol. Rapid Commun., 24, 875–878.

135. Lim, J., Lee, S.S., and Ying, J.Y. (2010) Chem. Commun., 46, 806–808.

136. Michrowska, A., Mennecke, K., Kunz, U., Kirschning, A., and Grela, K. (2006) J. Am. Chem. Soc., 128, 13261–13267.

137. Sandee, A.J., Petra, D.G.I., Reek, J.N.H., Kamer, P.C.J., and van Leeuwen, P.W.N.M. (2001) Chem. Eur. J., 7, 1202–1208.

138. Laue, S., Greiner, L., Wöltinger, L., and Liese, A. (2001) Adv. Synth. Catal., 343, 711–720.

139. Marcos, R., Jimeno, C., and Pericàs, M.A. (2011) Adv. Synth. Catal., 353, 1345–1352.

140. Shi, L., Wang, X., Sandoval, C.A., Wang, Z., Li, H., Wu, J., Yu, L., and Ding, K. (2009) Chem. Eur. J., 15, 9855–9867.

141. Popa, D., Marcos, R., Sayalero, S., Vidal-Ferran, A., and Pericàs, M.A. (2009) Adv. Synth. Catal., 351, 1539–1556.

142. Burguete, M.I., Cornejo, A., García-Verdugo, E., García, J., Gil, M.J., Luis, S.V., Martínez-Merino, V., Mayoral, J.A., and Sokolova, M. (2007) Green Chem., 9, 1091–1096.

143. Burguette, M.I., Cornejo, A., Garcá-Verdugo, E., Gil, M.J., Luis, S.V., Mayoral, J.A., Martínez-Merino, V., and Sokolova, M. (2007) J. Org. Chem., 72, 4344–4350.

144. Aranda, C., Cornejo, A., Fraile, J.M., García-Verdugo, E., Gil, M.J., Mayoral, J.A., Martínez-Merino, V., and Ochoa, Z. (2011) Green Chem., 13, 983–990.

145. Lim, J., Riduan, S.N., Lee, S.S., and Ying, J.Y. (2008) Adv. Synth. Catal., 350, 1295–1308.

146. Takeda, K., Oohara, T., Shimada, N., Nambu, H., and Hashimoto, S. (2011) Chem. Eur. J., 17, 13992–13998.

147. Berkessel, A. and Gröger, H. (2005) Asymmetric Organocatalysis, Wiley-VCH Verlag GmbH, Weinheim.

148. Kristensen, T.E. and Hansen, T. (2010) Eur. J. Org. Chem., 3179–3204.

149. Angelletti, E., Canepa, C., Martinetti, G., and Venturello, P. (1989) J. Chem. Soc., Perkin Trans. 1, 105–107.

150. Jackson, T., Clark, J.H., Macquarrie, D.J., and Brophy, J.H. (2004) Green Chem., 6, 193–195.

151. Pandarus, V., Gingras, G., Béland, F., Ciriminna, R., and Pagliaro, M. (2011) Catal. Sci. Technol., 1, 1600–1604.

152. Baumann, M., Baxendale, I.R., Ley, S.V., Smith, C.D., and Tranmer, G.K. (2006) Org. Lett., 8, 5231–5234.

153. Smith, C.J., Iglesias-Sigüenza, F.J., Baxendale, I.R., and Ley, S.V. (2007) Org. Biomol. Chem., 5, 2759–2761.

154. Zvagulis, A., Bonollo, S., Lanari, D., Pizzo, F., and Vaccaro, L. (2010) Adv. Synth. Catal., 352, 2489–2496.

155. Bogdan, A.R., Mason, B.P., Sylvester, K.T., and McQuade, D.T. (2007) Angew. Chem., Int. Ed., 46, 1698–1701.

156. Bogdan, A. and McQuade, D.T. (2009) Beilstein J. Org. Chem., 5, No. 17.

157. Hafez, A.M., Taggi, A.E., Dudding, T., and Lectka, T. (2001) J. Am. Chem. Soc., 123, 10853–10859.

158. Massi, A., Cavazzini, A., Zoppo, L.D., Pandoli, O., Costa, V., Pasti, L., and Giovannini, P.P. (2011) Tetrahedron Lett., 52, 619–622.

159. Demuynck, A.L.W., Peng, L., de Clippel, F., Vanderleyden, J., Jacob, P.A., and Sels, B.F. (2011) Adv. Synth. Catal., 353, 725–732.

160. Ayars, C., Henseler, A.H., and Pericàs, M.A. (2012) ChemSusChem, 5, 320–325.

161. Bortnolini, O., Caciolli, L., Cavazzini, A., Costa, V., Greco, R., Massi, A., and Pasti, L. (2012) Green Chem., 14, 992–1000.

162. Alza, E., Rodríguez-Escrich, C., Sayalero, S., Bastero, A., and Pericàs, M.A. (2009) Chem. Eur. J., 15, 10167–10172.

163. Ötvös, S.B., Mándity, I.M., and Fülöp, F. (2012) ChemSusShem, 5, 266–269.

164. Alza, E., Sayalero, S., Cambeiro, X.C., Martín-Rapún, R., Miranda, P.O., and Pericàs, M.A. (2011) Synlett, 464–468.

165. Cambeiro, X.C., Martín-Rapún, R., Miranda, P.O., Sayalero, S., Alza, E., Llanes, P., and Pericàs, M.A. (2011) Beilstein J. Org. Chem., 7, 1486–1493.

166. Bernstein, D., France, S., Wolfer, J., and Lectka, T. (2005) Tetrahedron: Asymmetry., 16, 3481–3483.

167. Bonfils, F., Cazzaux, I., Hodge, P., and Caze, C. (2006) Org. Biomol. Chem., 4, 493–497.

168. Asanomi, Y., Yamaguchi, H., Miyazaki, M., and Maeda, H. (2011) Molecules, 16, 6041–6059.

169. Hickey, A.M., Marle, L., McCreedy, T., Watts, P., Greenway, G.M., and Littlechild, J.A. (2007) Biochem. Soc. Trans., 35, 1621–1623.

170. Yuryev, R., Strompen, S., and Liese, A. (2011) Beilstein J. Org. Chem., 7, 1449–1467.

171. Matosevic, S., Szita, N., and Baganz, F. (2011) J. Chem. Technol. Biotechnol., 86, 325–334.

172. Honda, T., Miyazaki, M., Nakamura, H., and Maeda, H. (2006) Adv. Synth. Catal., 348, 2163–2171.

173. Honda, T., Miyazaki, M., Yamaguchi, Y., Nakamura, H., and Maeda, H. (2007) Lab Chip, 7, 366–372.

174. Dräger, G., Kiss, C., Kunz, U., and Kirschning, A. (2007) Org. Biomol. Chem., 5, 3657–3664.

175. Webb, D. and Jamison, T.F. (2010) Chem. Sci., 1, 675–680.

176. Wegner, J., Ceylan, S., and Kirschning, A. (2012) Adv. Synth. Catal., 354, 17–57.

177. Glasnov, T.N. and Kappe, C.O. (2010) Adv. Synth. Catal., 352, 3089–3097.

178. Petersen, T.P., Ritzén, A., and Ulven, T. (2009) Org. Lett., 11, 5134–5137.

179. Hopkin, M.D., Baxendale, I.R., and Ley, S.V. (2010) Chem. Commun., 46, 2450–2452.

180. France, S., Bernstein, D., Weatherwax, A., and Leckta, T. (2005) Org. Lett., 7, 3009–3012.

181. Luckarift, H.R., Nadeau, L.J., and Spain, J.C. (2005) Chem. Commun., 383–384.

182. Baxendale, I.R., Griffiths-Jones, C.M., Ley, S.V., and Tranmer, G.F. (2006) Synlett, 427–430.

183. Wiles, C., Watts, P., and Haswell, S.J. (2007) Lab Chip, 7, 322–330.

184. Baxendale, I.R., Ley, S.V., Mansfield, A.C., and Smith, C.D. (2009) Angew. Chem., Int. Ed., 48, 4017–4021.

185. Brasholz, M., Macdonald, J.M., Saubern, S., Ryan, J.H., and Holmes, A.B. (2010) Chem. Eur. J., 16, 11471–11480.

186. Qian, Z., Baxendale, I.R., and Ley, S.V. (2010) Synlett, 505–508.

187. Obermayer, D., Glasnov, T.N., and Kappe, C.O. (2011) J. Org. Chem., 76, 6657–6669.

188. Martin, L.J., Marzinzik, A.L., Ley, S.V., and Baxendale, I.R. (2011) Org. Lett., 13, 320–323.

189. Lange, H., Carter, C.F., Hopkin, M.D., Burke, A., Goode, J.G., Baxendale, I.R., and Ley, S.V. (2011) Chem. Sci., 2, 765–769.

190. Battilocchio, C., Baumann, M., Baxendale, I.R., Biava, M., Kitching, M.O., Ley, S.V., Martin, R.E., Ohnmacht, S.A., and Tappin, N.D.C. (2012) Synthesis, 44, 635–647.