Immobilized transition metals as catalysts for cross-couplings in continuous flow - A critical assessment of the reaction mechanism and metal leaching

ChemCatChem

Volumn 6, Issue 12, 2015, Pages 3286-3305

  Cantillo, David ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

continuous flow chemistry; cross coupling; heterogeneous catalysis; homogeneous catalysis; palladium

Indexed keywords

EID: 84914140067     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201402483     Document Type: Article

References (202)

1. J. Hartwig, J. B. Metternich, N. Nikbin, A. Kirschning, S. V. Ley, Org. Biomol. Chem. 2014, 12, 3611-3615
2. C. Wiles, P. Watts, Green Chem. 2014, 16, 55-62
3. K. S. Elvira, X. C. Solvas, R. C. R. Wootton, A. J. deMello, Nat. Chem. 2013, 5, 905-915
4. J.-i. Yoshida, Drug Discovery Today 2013, 10, e 53 -e 59
5. I. R. Baxendale, L. Broken, C. J. Mallia, Green Process. Synth. 2013, 2, 211-230
6. I. R. Baxendale, J. Chem. Technol. Biotechnol. 2013, 88, 519-552
7. S. G. Newman, K. F. Jensen, Green Chem. 2013, 15, 1456-1472
8. C. Wiles, P. Watts, Green Chem. 2012, 14, 38-54
9. M. Baumann, I. R. Baxendale, S. V. Ley, Mol. Diversity 2011, 15, 613-630
10. J.-i. Yoshida, H. Kim, A. Nagaki, ChemSusChem 2011, 4, 331-340.
11. Microreactors in Preparative Chemistry (Ed.:, W. Reschetilowski,), Wiley-VCH, Weinheim, 2013
12. Microreactors in Organic Synthesis and Catalysis, 2n ed. (Ed.:, T. Wirth,), Wiley-VCH, Weinheim, 2013
13. Handbook of Micro Reactors (Eds.:, V. Hessel, J. C. Schouten, A. Renken, Y. Wang, J.-i. Yoshida,), Wiley-VCH, Weinheim, 2009
14. Chemical Reactions and Processes under Flow Conditions (Ed.:, S. V. Luis, E. Garcia-Verdugo,), RSC Green Chemistry, 2010
15. Microreactors: New Technology for Modern Chemistry. (Eds.:, W. Ehrfeld, V. Hessel, H. Löwe,), Wiley-VCH, Weinheim, 2000.
16. C. Wiles, P. Watts, Micro Reaction Technology in Organic Synthesis, CRC Press, Boca Raton, 2011, chap. 7, pp. 347-384.
17. D. M. Roberge, M. Gottsponer, M. Eyholzer, N. Kockmann, Chem. Today 2009, 27, 8-11
18. D. M. Roberge, B. Zimmermann, F. Rainone, M. Gottsponer, M. Eyholzer, N. Kockmann, Org. Process Res. Dev. 2008, 12, 905-910
19. H. Pennemann, P. Watts, S. J. Haswell, V. Hessel, H. Löwe, Org. Process Res. Dev. 2004, 8, 422-439.
20. V. Hessel, D. Kralisch, N. Kockmann, T. Noel, Q. Wang, ChemSusChem 2013, 6, 746-789, and references therein.
21. D. T. McQuade, P. H. Seeberger, J. Org. Chem. 2013, 78, 6384-6389
22. D. Webb, T. F. Jamison, Chem. Sci. 2010, 1, 675-680
23. J. Wegner, S. Ceylan, A. Kirschning, Adv. Synth. Catal. 2012, 354, 17-57
24. J. C. Pastre, D. L. Browne, S. V. Ley, Chem. Soc. Rev. 2013, 42, 8849-8869.
25. I. R. Baxendale, J. Deeley, C. M. Griffiths-Jones, S. V. Ley, S. Saaby, G. K. Tranmer, Chem. Commun. 2006, 2566-2568
26. A. R. Bogdan, S. L. Poe, D. C. Kubis, S. J. Broadwater, D. T. McQuade, Angew. Chem. Int. Ed. 2009, 48, 8547-8550
27. Angew. Chem. 2009, 121, 8699-8702
28. P. T. Petersen, A. Ritzén, T. Ulven, Org. Lett. 2009, 11, 5134-5137
29. F. Lévesque, P. H. Seeberger, Angew. Chem. Int. Ed. 2012, 51, 1706-1709
30. Angew. Chem. 2012, 124, 1738-1741
31. M. D. Hopkin, I. R. Baxendale, S. V. Ley, Org. Biomol. Chem. 2013, 11, 1822-1839
32. D. R. Snead, T. F. Jamison, Chem. Sci. 2013, 4, 2822-2827
33. S. Mascia, P. L. Heider, H. Zhang, R. Lakerveld, B. Benyahia, P. I. Barton, R. D. Braatz, C. L. Cooney, J. M. B. Evans, T. F. Jamison, K. F. Jensen, A. S. Myerson, B. L. Trout, Angew. Chem. Int. Ed. 2013, 52, 12359-12363
34. Angew. Chem. 2013, 125, 12585-12589
35. A. R. Longstreet, S. M. Opalka, B. S. Campbell, B. F. Gupton, D. T. McQuade, Beilstein J. Org. Chem. 2013, 9, 2570-2578
36. L. Dalla-Vechia, B. Reichart, T. Glasnov, L. S. M. Miranda, C. O. Kappe, R. O. M. A. de Souza, Org. Biomol. Chem. 2013, 11, 6806-6813
37. J. Hartwig, S. Ceylan, L. Kupracz, L. Coutable, A. Kirschning, Angew. Chem. Int. Ed. 2013, 52, 9813-9817
38. Angew. Chem. 2013, 125, 9995-9999
39. L. Kupracz, A. Kirschning, Adv. Synth. Catal. 2013, 355, 3375-3380.
40. J. R. H. Ross, Heterogeneous Catalysis: Fundamentals and Applications, Elsevier, Amsterdam, 2012
41. G. Ertl, H. Knözinger, F. Schüth, J. Weitkamp, Handbook of Heterogeneous Catalysis, Wiley-VCH, Weinheim, 2008
42. Fine Chemicals through Heterogeneous Catalysis, (Eds.:, R. A. Sheldon, H. van Bekkum,), Wiley-VCH, Weinheim, 2001.
43. Immobilized Catalysts. Solid Phases, Immobilization and Applications. Series: Topics in Current Chemistry, Vol. 242 (Ed.:, A. Kirschning,), Springer, Berlin, 2004.
44. C. G. Frost, L. Mutton, Green Chem. 2010, 12, 1687-1703.
45. M. Irfan, T. N. Glasnov, C. O. Kappe, ChemSusChem 2011, 4, 300-316.
46. C. C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot, V. Snieckus, Angew. Chem. Int. Ed. 2012, 51, 5062-5085
47. Angew. Chem. 2012, 124, 5150-5174.
48. Science of Synthesis: Cross Coupling and Heck Type Reactions, Vols. 1-3 (Eds.:, G. A. Molander, J. P. Wolf, M. Larhed,), Georg Thieme Verlag, Stuttgart, 2013
49. Metal Catalyzed Cross-Coupling Reactions and More (Eds.:, A. de Meijere, S. Bräse, M. Oestreich,), Wiley-VCH, Weinheim, 2014.
50. T. Takahashi, K.-i. Kanno, in Modern Organonickel Chemistry, (Ed.:, Y. Tamaru,), Wiley-VCH, Weinheim, 2005, pp. 41-53
51. Copper-Mediated Cross-Coupling Reactions (Eds.:, G. Evano, N. Blanchard,), Wiley, New Jersey, 2014.
52. J. Bariwal, E. van der Eycken, Chem. Soc. Rev. 2013, 42, 9283-9303
53. F. Monnier, M. Taillefer, Angew. Chem. Int. Ed. 2009, 48, 6954-6971
54. Angew. Chem. 2009, 121, 7088-7105
55. S. V. Ley, A. W. Thomas, Angew. Chem. Int. Ed. 2003, 42, 5400-5449
56. Angew. Chem. 2003, 115, 5558-5607.
57. A. Molnár, Chem. Rev. 2011, 111, 2251-2320
58. E. B. Anderson, M. R. Buchmeiser, ChemCatChem 2012, 4, 30-33.
59. T. Noël, S. L. Buchwald, Chem. Soc. Rev. 2011, 40, 5010-5029.
60. M. Pagliaro, V. Pandarus, R. Ciriminna, F. Bland, P. Demma Carà, ChemCatChem 2012, 4, 432-445.
61. R. Narayanan, M. A. El-Sayed, J. Am. Chem. Soc. 2003, 125, 8340-8347
62. R. Narayanan, M. A. El-Sayed, J. Phys. Chem. B 2003, 107, 12416-12424.
63. A. H. M. de Vries, J. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285-3288
64. J. G. de Vries, Dalton Trans. 2006, 421-429.
65. F. Zhao, B. M. Bhanage, M. Shirai, M. Arai, Chem. Eur. J. 2000, 6, 843-848
66. B. M. Bhanage, M. Shirai, M. Arai, J. Mol. Catal. A 1999, 145, 69-74.
67. M. T. Reetz, E. Westermann, Angew. Chem. Int. Ed. 2000, 39, 165-168
68. Angew. Chem. 2000, 112, 170-173
69. M. T. Reetz, W. Helbig, S. A. Quasier, U. Stimming, N. Breuer, R. Vogel, Science 1995, 267, 367-369.
70. M. B. Thathagar, J. E. ten Elshof, G. Rothenberg, Angew. Chem. Int. Ed. 2006, 45, 2886-2890
71. Angew. Chem. 2006, 118, 2952-2956
72. A. V. Gaikwad, A. Holuigue, M. B. Thathagar, J. E. ten Elhof, G. Rothenberg, Chem. Eur. J. 2007, 13, 6908-6913.
73. V. P. Ananikov, I. P. Beletskaya, Organometallics 2012, 31, 1595-1604
74. A. S. Kashin, V. P. Ananikov, J. Org. Chem. 2013, 78, 11117-11125.
75. J.-S. Chen, A. N. Vasiliev, A. P. Pannarello, J. G. Khinast, Appl. Catal. A 2007, 325, 76-86.
76. R. K. Arvela, N. E. Leadbeater, M. S. Sangi, V. A. Williams, P. Granados, R. D. Singer, J. Org. Chem. 2005, 70, 161-168
77. A. K. Diallo, C. Ornelas, L. Salmon, J. R. Aranzaes, D. Astruc, Angew. Chem. Int. Ed. 2007, 46, 8644-8648
78. Angew. Chem. 2007, 119, 8798-8802
79. A. Alimardanov, L. S. V. de Vondervoort, A. H. M. de Vries, J. G. de Vries, Adv. Synth. Catal. 2004, 346, 1812-1817
80. C. Deraedt, D. Astruc, Acc. Chem. Res. 2014, 47, 494-503.
81. N. E. Leadbeater, M. Marco, Angew. Chem. Int. Ed. 2003, 42, 1407-1409
82. Angew. Chem. 2003, 115, 1445-1447
83. R. K. Arvela, N. E. Leadbeater, M. S. Sangi, V. A. Williams, P. Granados, R. D. Singer, J. Org. Chem. 2005, 70, 161-168
84. R. A. D. Arancon, C. S. K. Lin, C. Vargas, R. Luque, Org. Biomol. Chem. 2014, 12, 10-35.
85. N. E. Leadbeater, Nat. Chem. 2010, 2, 1007-1009
86. I. Thomé, A. Nijs, C. Bolm, Chem. Soc. Rev. 2012, 41, 979-987.
87. D. A. Conlon, B. Pipik, S. Ferdinand, C. R. LeBlond, J. R. Sowa, B. Izzo, P. Collins, G.-J. Ho, J. M. Williams, Y.-J. Shi, Y. Sun, Adv. Synth. Catal. 2003, 345, 931-935.
88. S. MacQuarrie, J. H. Horton, J. Barnes, K. McEleney, H.-P. Loock, C. M. Crudden, Angew. Chem. Int. Ed. 2008, 47, 3279-3282
89. Angew. Chem. 2008, 120, 3324-3328.
90. G. M. Greenway, S. J. Haswell, D. O. Morgan, V. Skelton, P. Styring, Sens. Actuators B 2000, 63, 153-158
91. P. He, S. J. Haswell, P. D. I. Fletcher, Lab Chip 2004, 4, 38-41
92. P. He, S. J. Haswell, P. D. I. Fletcher, Appl. Catal. A 2004, 274, 111-114.
93. J. B. Brazier, B. N. Nguyen, L. A. Adrio, E. M. Barreiro, W. P. Leong, M. A. Newton, S. J. A. Figueroa, K. Hellgardt, K. K. M. Hii, Catal. Today 2014, 229, 95-103.
94. S. C. Stouten, Q. Wang, T. Noel, V. Hessel, Tetrahedron Lett. 2013, 54, 2194-2198.
95. P. L. Lau, R. W. K. Allen, P. Styring, Beilstein J. Org. Chem. 2013, 9, 2886-2897.
96. C. Battilocchio, B. N. Bhawal, R. Chorghade, B. J. Deadman, J. M. Hawkins, S. V. Ley, Isr. J. Chem. 2014, 54, 371-380.
97. L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133-173.
98. F.-X. Felpin, Synlett 2014, 25, 1055-1067.
99. D. A. Snyder, C. Noti, P. H. Seeberger, F. Schael, T. Bieber, G. Rimmel, W. Ehrfeld, Helv. Chim. Acta 2005, 88, 1-9.
100. C. Mateos, J. A. Rincon, B. Martín-Hidalgo, J. Villanueva, Tetrahedron Lett. 2014, 55, 3701-3705.
101. X. Fan, M. Gonzalez Manchon, K. Wilson, S. Tennison, A. Kozynchenko, A. A. Lapkin, P. K. Plucinski, J. Catal. 2009, 267, 114-120.
102. Y. Suzuki, P. Laurino, D. T. McQuade, P. H. Seeberger, Helv. Chim. Acta 2012, 95, 2578-2588.
103. T. N. Glasnov, S. Findenig, C. O. Kappe, Chem. Eur. J. 2009, 15, 1001-1010.
104. For a review on the translation of microwave batch to conventionally heated flow protocols (microwave-to-flow paradigm), see:, T. N. Glasnov, C. O. Kappe, Chem. Eur. J. 2011, 17, 11956-11968.
105. K. S. A. Vallin, M. Larhed, A. Hallberg, J. Org. Chem. 2001, 66, 4340-4343.
106. M. Fuchs, W. Goessler, C. Pilger, C. O. Kappe, Adv. Synth. Catal. 2010, 352, 323-328
107. For a review of copper-catalyzed azide-alkyne cycloadditions in continuous flow, see:, C. O. Kappe, E. Van der Eycken, Chem. Soc. Rev. 2010, 39, 1280-1290.
108. Polymeric Materials in Organic Synthesis and Catalysis (Ed.:, M. R. Buchmeiser,), Wiley-VCH, Weinheim, 2003.
109. W. Solodenko, U. Kunz, G. Jas, A. Kirschning, Bioorg. Med. Chem. Lett. 2002, 12, 1833-1835
110. A. Kirschning, C. Altwicker, G. Dräger, J. Harders, N. Hoffmann, U. Hoffmann, H. Schönfeld, W. Solodenko, U. Kunz, Angew. Chem. Int. Ed. 2001, 40, 3995-3998
111. Angew. Chem. 2001, 113, 4118-4120.
112. W. Solodenko, H. Wen, S. Leue, F. Stuhlmann, G. Sourkouni-Argirusi, G. Jas, H. Schönfeld, U. Kunz, A. Kirschning, Eur. J. Org. Chem. 2004, 3601-3610.
113. K. Mennecke, A. Kirschning, Beilstein J. Org. Chem. 2009, 5, DOI:.
114. U. Kunz, A. Kirschning, H.-L. Wen, W. Solodenko, R. Cecilia, C. O. Kappe, T. Turek, Catal. Today 2005, 105, 318-324
115. K. Mennecke, R. Cecilia, T. N. Glasnov, S. Gruhl, C. Vogt, A. Feldhoff, M. A. L. Vargas, C. O. Kappe, U. Kunz, A. Kirschning, Adv. Synth. Catal. 2008, 350, 717-730.
116. K. Mennecke, W. Solodenko, A. Kirschnig, Synthesis 2008, 1589-1599
117. K. Mennecke, A. Kirschnig, Synthesis 2008, 3267-3272.
118. M. B. Gawande, P. S. Branco, R. S. Varma, Chem. Soc. Rev. 2013, 42, 3371-3393
119. S. Shylesh, V. Schunemann, W. R. Thiel, Angew. Chem. Int. Ed. 2010, 49, 3428-3459
120. Angew. Chem. 2010, 122, 3504-3537.
121. S. Ceylan, C. Friese, C. Lammel, K. Mazac, A. Kirschning, Angew. Chem. Int. Ed. 2008, 47, 8950-8953
122. Angew. Chem. 2008, 120, 9083-9086
123. S. Ceylan, L. Coutable, J. Wegner, A. Kirschning, Chem. Eur. J. 2011, 17, 1884-1893.
124. Inductive heating of copper wires was also employed for catalyzing azide-alkyne cycloadditions in continuous flow:, S. Ceylan, T. Klande, C. Vogt, C. Friese, A. Kirschning, Synlett 2010, 13, 2009-2013.
125. N. Nikbin, M. Ladlow, S. V. Ley, Org. Process Res. Dev. 2007, 11, 458-462.
126. P. He, S. J. Haswell, P. D. I. Fletcher, S. M. Kelly, A. Mansfield, Beilstein J. Org. Chem. 2011, 7, 1150-1157
127. G. Chaplain, S. J. Haswell, P. D. I. Fletcher, S. M. Kelly, A. Mansfield, Aust. J. Chem. 2013, 66, 208-212.
128. F. Benaskar, N. G. Patil, V. Engels, E. V. Rebrov, J. Meuldijk, L. A. Hulshof, V. Hessel, A. E. H. Wheatley, J. C. Shouten, Chem. Eng. J. 2012, 207-208, 426-439
129. F. Benaskar, N. G. Patil, E. V. Rebrov, A. Ben-Abdelmoumen, J. Meuldijk, L. A. Hulshof, V. Hessel, A. E. H. Wheatley, J. C. Shouten, ChemSusChem 2013, 6, 353-366.
130. E. Comer, M. G. Organ, J. Am. Chem. Soc. 2005, 127, 8160-8167.
131. G. Shore, S. Morin, M. G. Organ, Angew. Chem. Int. Ed. 2006, 45, 2761-2766
132. Angew. Chem. 2006, 118, 2827-2832
133. For a detailed discussion of the temperatures reached in these microwave-heated experiments, see:, G. Shore, W. J. Yoo, C. J. Li, M. G. Organ, Chem. Eur. J. 2010, 16, 126-133.
134. G. Shore, S. Morin, D. Mallik, M. G. Organ, Chem. Eur. J. 2008, 14, 1351-1356.
135. B. Gutmann, T. N. Glasnov, T. Razzaq, W. Goessler, D. M. Roberge, C. O. Kappe, Beilstein J. Org. Chem. 2011, 7, 503-517.
136. Y. Zhang, T. F. Jamison, S. Patel, N. Mainolfi, Org. Lett. 2011, 13, 280-283.
137. L.-M. Tan, Z.-Y. Sem, W.-Y. Chong, X. Liu, Hendra, W. L. Kwan, C.-L. K. Lee, Org. Lett. 2013, 15, 65-67.
138. C. Ramarao, S. V. Ley, S. C. Smith, I. M. Shirley, N. DeAlmeida, Chem. Commun. 2002, 1132-1133.
139. Y. Y. Kuang, F. R. Chen, Helv. Chim. Acta 2009, 92, 897-903
140. A. Carpita, A. Ribecai, Tetrahedron Lett. 2009, 50, 204-207.
141. C. K. Y. Lee, A. B. Holmes, S. V. Ley, I. F. McConvey, B. Al-Duri, C. A. Leecke, R. C. D. Santos, J. P. K. Seville, Chem. Commun. 2005, 2175-2177.
142. G. A. Leeke, R. C. D. Santos, B. Al-Duri, J. P. K. Seville, C. J. Smith, C. K. Y. Lee, A. B. Holmes, I. F. McConvey, Org. Process Res. Dev. 2007, 11, 144-148.
143. S. J. Broadwater, D. T. McQuade, J. Org. Chem. 2006, 71, 2131-2134.
144. I. R. Baxendale, C. M. Griffiths-Jones, S. V. Ley, G. K. Tranmer, Chem. Eur. J. 2006, 12, 4407-4416.
145. D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070
146. Angew. Chem. 1995, 107, 1159-1171.
147. R. J. Lundgren, M. Stradiotto, Chem. Eur. J. 2012, 18, 9758-9769.
148. K. M. Engle, J.-Q. Yu, J. Org. Chem. 2013, 78, 8927-8955.
149. C. A. Fleckenstein, H. Plenio, Chem. Soc. Rev. 2010, 39, 694-711.
150. G. R. Yang, G. Bae, J. Choe, S. Lee, K. H. Song, Bull. Korean Chem. Soc. 2010, 31, 250-252.
151. B. Borcsek, G. Bene, G. Szirbik, G. Dormán, R. Jones, L. Ürge, F. Darvas, ARKIVOC 2012, 2012, 186-195.
152. V. Pandarus, G. Gingras, F. Béland, R. Ciriminna, M. Pagliaro, Org. Process Res. Dev. 2012, 16, 117-122
153. M. Lemay, V. Pandarus, M. Simard, O. Marion, L. Tremblay, F. Béland, Top. Catal. 2010, 53, 1059-1062.
154. J. M. Muñoz, J. Alcázar, A. de La Hoz, A. Díaz-Ortiz, Adv. Synth. Catal. 2012, 354, 3456-3460.
155. B. Egle, J. M. Muñoz, N. Alonso, W. M. De Borggraeve, A. de La Hoz, A. Diaz-Ortiz, J. Alcázar, J. Flow Chem. 2014, 4, 22-25.
156. V. Pandarus, G. Gingras, F. Béland, R. Ciriminna, M. Pagliaro, Org. Process Res. Dev. DOI:.
157. V. Pandarus, G. Gingras, F. Béland, R. Ciriminna, M. Pagliaro, Org. Process Res. Dev. DOI:.
158. C. J. Whiteoak, G. Salassa, A. W. Kleij, Chem. Soc. Rev. 2012, 41, 622-631
159. A. W. Kleij, Eur. J. Inorg. Chem. 2008, 193-205
160. S. J. Wezenberg, A. W. Kleij, Angew. Chem. Int. Ed. 2008, 47, 2354-2364
161. Angew. Chem. 2008, 120, 2388-2399
162. P. G. Cozzi, Chem. Soc. Rev. 2004, 33, 410-421.
163. N. T. S. Phan, D. H. Brown, H. Adams, S. E. Spey, P. Styring, Dalton Trans. 2004, 1348-1357
164. N. T. S. Phan, D. H. Brown, P. Styring, Tetrahedron Lett. 2004, 45, 7915-7919
165. N. T. S. Phan, P. Styring, Green Chem. 2008, 10, 1055-1060
166. S. R. Borhade, S. B. Waghmode, Tetrahedron Lett. 2008, 49, 3423-3429
167. T. Kylmälä, N. Kuuloja, Y. Xu, K. Rissanen, R. Franzén, Eur. J. Org. Chem. 2008, 4019-4024
168. P. Liu, X.-J. Feng, R. He, Tetrahedron 2010, 66, 631-636
169. M. J. Matos, S. Vazquez-Rodriguez, F. Borges, L. Santana, E. Uriarte, Tetrahedron Lett. 2011, 52, 1225-1227.
170. Z. Wu, Z. Jiang, D. Wu, H. Xiang, X. Zhou, Eur. J. Org. Chem. 2010, 1854-1857
171. Z. Wu, L. Zhou, Z. Jiang, D. Wu, Z. Li, X. Zhou, Eur. J. Org. Chem. 2010, 4971-4975
172. L. Yu, X. Jiang, L. Wang, Z. Li, D. Wu, X. Zhou, Eur. J. Org. Chem. 2010, 5560-5562
173. A. Gogoi, G. Sarmah, A. Dewan, U. Bora, Tetrahedron Lett. 2014, 55, 31-35.
174. S. J. Haswell, B. O'Sullivan, P. Styring, Lab Chip 2001, 1, 164-166.
175. N. T. S. Phan, D. H. Brown, P. Styring, Green Chem. 2004, 6, 526-532.
176. P. Styring, A. I. R. Parracho, Beilstein J. Org. Chem. 2009, 5, DOI:.
177. N. T. S. Phan, J. Khan, P. Styring, Tetrahedron 2005, 61, 12065-12073.
178. Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.:, E.-i. Negishi,), Wiley, New York, 2002.
179. G. C. Fortman, S. P. Nolan, Chem. Soc. Rev. 2011, 40, 5151-5169.
180. K. F. Bolton, A. J. Canty, J. A. Deverell, R. M. Guijt, E. F. Hilder, T. Rodemann, J. A. Smith, Tetrahedron Lett. 2006, 47, 9321-9324.
181. J. A. Deverell, T. Rodemann, J. A. Smith, A. J. Canty, R. M. Guijt, Sens. Actuators B 2011, 155, 388-396.
182. A. Gömann, J. A. Deverell, K. F. Munting, R. C. Jones, T. Rodemann, A. J. Canty, J. A. Smith, R. M. Guijt, Tetrahedron 2009, 65, 1450-1454.
183. R. C. Jones, A. J. Canty, J. A. Deverell, M. G. Gardiner, R. M. Guijt, T. Rodemann, J. A. Smith, V.-A. Tolhurst, Tetrahedron 2009, 65, 7474-7481.
184. W. R. Reynolds, P. Plucinski, C. G. Frost, Catal. Sci. Technol. 2014, 4, 948-954.
185. C. Pavia, E. Ballerini, L. A. Bivona, F. Giacalone, C. Aprile, L. Vaccaro, M. Gruttadauria, Adv. Synth. Catal. 2013, 355, 2007-2018.
186. N. Karbass, V. Sans, E. Garcia-Verdugo, M. I. Burguete, S. V. Luis, Chem. Commun. 2006, 3095-3097.
187. V. Solodenko, K. Menneke, C. Vogt, S. Gruhl, A. Kirschning, Synthesis 2006, 1873-1881.
188. M. Irfan, E. Petricci, T. N. Glasnov, M. Taddei, C. O. Kappe, Eur. J. Org. Chem. 2009, 1326-1334.
189. M. Chen, J. Xiao, H.-P. Steinrück, S. Wang, W. Wang, N. Lin, W. Hieringer, J. M. Gottfried, J. Phys. Chem. C 2014, 118, 6820-6830, and references therein.
190. L. Fiebig, H.-G. Schmalz, M. Schäfer, Int. J. Mass Spectrom. 2011, 308, 307-310
191. A. A. Sabino, A. H. L. Machado, C. R. D. Correia, M. N. Eberlin, Angew. Chem. Int. Ed. 2004, 43, 2514-2518
192. Angew. Chem. 2004, 116, 2568-2572
193. X. He, S. Zhang, Y. Guo, H. Wang, G. Lin, Organometallics 2012, 31, 2945-2948
194. A. H. L. Machado, H. M. S. Milagre, L. S. Eberlin, A. A. Sabino, C. R. D. Correia, M. N. Eberlin, Org. Biomol. Chem. 2013, 11, 3277-3281.
195. S. Saaby, K. R. Knudsen, M. Ladlow, S. V. Ley, Chem. Commun. 2005, 2909-2911
196. B. Desai, C. O. Kappe, J. Comb. Chem. 2005, 7, 641-643.
197. T. N. Glasnov, C. O. Kappe, Adv. Synth. Catal. 2010, 352, 3089-3097
198. M. Viviano, T. N. Glasnov, B. Reichart, G. Tekautz, C. O. Kappe, Org. Process Res. Dev. 2011, 15, 858-870
199. P. Li, J. S. Moore, K. F. Jensen, ChemCatChem 2013, 5, 1729-1733.
200. D. Ormerod, B. Bongers, W. Porto-Carrero, S. Ciegas, G. Vijt, N. Lefevre, D. Lauwers, W. Brusten, A. Buekenhoudt, RSC Adv. 2013, 3, 21501-21510
201. L. Peeva, J. Arbour, A. Livingston, Org. Process Res. Dev. 2013, 17, 967-975
202. L. Peeva, J. da Silva Burgal, S. Vartak, A. G. Livingston, J. Catal. 2013, 306, 190-201.