C−H Functionalisation for Hydrogen Isotope Exchange

Angewandte Chemie - International Edition

Volumn 57, Issue 12, 2018, Pages 3022-3047

  Atzrodt, Jens ^a   Derdau, Volker ^a   Kerr, William J ^b   Reid, Marc ^b  

^a Isotope Chemistry and Metabolite Synthesis   (Germany)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

catalysis; C H functionalization; drug discovery; hydrogen isotope exchange

Indexed keywords

CATALYSIS; ISOTOPES;

C-H FUNCTIONALIZATION; DRUG DISCOVERY; FUNCTIONALISATION; HYDROGEN ISOTOPE; HYDROGEN ISOTOPE EXCHANGE; LIFE-SCIENCES; MOLECULAR ARCHITECTURE;

HYDROGEN;

EID: 85041173225     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201708903     Document Type: Review

References (281)

1. J. K. Kim, K. Shin, S. Chang in Topics in Organometallic Chemistry (Eds.: P. H. Dixneuf, H. Doucet), Springer, Cham, 2016;
2. C−H Bond Activation in Organic Synthesis (Ed.: L. J. Jack), CRC, Boca Raton, 2015;
3. C-H Activation, Vol. 26 of Topics in Current Chemistry (Eds.: J.-Q. Yu, Z. Shi), Springer, New York, 2010.
4. T. Cernak, K. D. Dykstra, S. Tyagarajan, P. Vachal, S. W. Krska, Chem. Soc. Rev. 2016, 45, 546–576;
5. T. Gensch, M. N. Hopkinson, F. Glorius, J. Wencel-Delord, Chem. Soc. Rev. 2016, 45, 2900–2936;
6. C. Borie, L. Ackermann, M. Nechab, Chem. Soc. Rev. 2016, 45, 1368–1386;
7. W. Liu, L. Ackermann, ACS Catal. 2016, 6, 3743–3752;
8. Y. Segawa, T. Maekawa, K. Itami, Angew. Chem. Int. Ed. 2015, 54, 66–81;
9. Angew. Chem. 2015, 127, 68–83;
10. J. Li, L. Ackermann, Nat. Chem. 2015, 7, 686–687;
11. G. Song, X. Li, Acc. Chem. Res. 2015, 48, 1007–1020;
12. N. Kuhl, N. Schroeder, F. Glorius, Adv. Synth. Catal. 2014, 356, 1443–1460;
13. S. A. Girard, T. Knauber, C.-J. Li, Angew. Chem. Int. Ed. 2014, 53, 74–100;
14. Angew. Chem. 2014, 126, 76–103;
15. G. Rouquet, N. Chatani, Angew. Chem. Int. Ed. 2013, 52, 11726–11743;
16. Angew. Chem. 2013, 125, 11942–11959;
17. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215–1292;
18. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212–11222;
19. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147;
20. I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890–931;
21. C. Coperet, Chem. Rev. 2010, 110, 656–680;
22. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624–655;
23. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677–685.
24. Y. Lu, D.-H. Wang, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 5916–5921;
25. J. A. Schiffner, T. H. Wöste, M. Oestreich, Eur. J. Org. Chem. 2010, 174–182;
26. B. Xiao, Y. Fu, J. Xu, T.-J. Gong, J.-J. Dai, J. Yi, L. Liu, J. Am. Chem. Soc. 2010, 132, 468–469;
27. F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9982–9983;
28. D.-H. Wang, K. M. Engle, B.-F. Shi, J.-Q. Yu, Science 2010, 327, 315–319;
29. M. Wasa, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3680–3681;
30. F. Wang, G. Song, X. Li, Org. Lett. 2010, 12, 5430–5433;
31. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Angew. Chem. Int. Ed. 2011, 50, 4169–4172;
32. Angew. Chem. 2011, 123, 4255–4258;
33. S. Rakshit, F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9585–9587;
34. N. Guimond, C. Gouliaras, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 6908–6909;
35. K. Morimoto, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 2068–2071.
36. X. Zhao, C. E. Dimitrijevi, V. M. Dong, J. Am. Chem. Soc. 2009, 131, 3466–3467;
37. X. Wang, T.-S. Mei, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 7520–7521;
38. T.-S. Mei, R. Giri, N. Maugel, J.-Q. Yu, Angew. Chem. Int. Ed. 2008, 47, 5215–5219;
39. Angew. Chem. 2008, 120, 5293–5297;
40. J.-J. Li, T.-S. Mei, J.-Q. Yu, Angew. Chem. Int. Ed. 2008, 47, 6452–6455;
41. Angew. Chem. 2008, 120, 6552–6555;
42. K. L. Hull, W. Q. Anani, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 7134–7135.
43. L. Ackermann, A. V. Lygin, N. Hofmann, Org. Lett. 2011, 13, 3278–3281;
44. S. H. Cho, J. Yoon, S. Chang, J. Am. Chem. Soc. 2011, 133, 5996–6005;
45. Q. Shuai, G. Deng, J. Chua, D. S. Bohle, C.-J. Li, Adv. Synth. Catal. 2010, 352, 632–636;
46. T.-S. Mei, X. Wang, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 10806–10807;
47. Q. Wang, S. L. Schreiber, Org. Lett. 2009, 11, 5178–5180;
48. D. Monguchi, T. Fujiwara, H. Furukawa, A. Mori, Org. Lett. 2009, 11, 1607–1610.
49. X. Wang, Y. Lu, H.-X. Dai, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 12203–12205;
50. Y.-H. Zhang, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 14654–14655;
51. D. C. Powers, M. A. L. Geibel, J. E. M. N. Klein, T. Ritter, J. Am. Chem. Soc. 2009, 131, 17050–17051;
52. L. V. Desai, K. J. Stowers, M. S. Sanford, J. Am. Chem. Soc. 2008, 130, 13285–13293.
53. J. Atzrodt, V. Derdau, T. Fey, J. Zimmermann, Angew. Chem. Int. Ed. 2007, 46, 7744–7765;
54. Angew. Chem. 2007, 119, 7890–7911.
55. W. J. S. Lockley, J. R. Heys, J. Labelled Compd. Radiopharm. 2010, 53, 635–644;
56. T. Junk, W. J. Catallo, Chem. Soc. Rev. 1997, 26, 401–406;
57. N. Elander, J. R. Jones, S.-Y. Lu, S. Stone-Elander, Chem. Soc. Rev. 2000, 29, 239–249;
58. M. Siskin, A. Katritzky, Chem. Rev. 2001, 101, 825–835;
59. J. R. Heys, J. Labelled Compd. Radiopharm. 2010, 53, 716–721;
60. Y. Sawama, Y. Monguchi, H. Sajiki, Synlett 2012, 23, 959–972.
61. M. Hatano, T. Nishimura, H. Yorimitsu, Org. Lett. 2016, 18, 3674–3677;
62. W. Bai, K. H. Lee, S. K. S. Tse, K. W. Chan, Z. Lin, G. Jia, Organometallics 2015, 34, 3686–3698;
63. S. Ma, G. Villa, P. S. Thuy-Boun, A. Homs, J.-Q. Yu, Angew. Chem. Int. Ed. 2014, 53, 734–737;
64. Angew. Chem. 2014, 126, 753–756;
65. N. Modutlwa, T. Maegawa, Y. Monguchi, H. Sajiki, J. Labelled Compd. Radiopharm. 2010, 53, 686–692.
66. D. Hesk, C. F. Lavey, P. McNamara, J. Labelled Compd. Radiopharm. 2010, 53, 722–730;
67. M. R. Chappelle, C. R. Hawes, J. Labelled Compd. Radiopharm. 2010, 53, 745–751;
68. C. N. Filer, J. Labelled Compd. Radiopharm. 2010, 53, 739–744;
69. S. R. Pollack, D. J. Schenk, J. Labelled Compd. Radiopharm. 2015, 58, 433–441;
70. V. P. Shevchenko, I. Y. Nagaev, N. F. Myasoedov, J. Labelled Compd. Radiopharm. 2010, 53, 693–703.
71. R. Voges, R. Heys, T. Moenius, Preparation of Compounds Labeled with Tritium and Carbon-14, Wiley, Chichester, 2009.
72. M. Larance, A. I. Lamond, Nat. Rev. Mol. Cell Biol. 2015, 16, 269–280.
73. S. L. Harbeson, R. D. Tung, Med. Chem. News 2014, 2, 8–22;
74. T. G. Gant, J. Med. Chem. 2014, 57, 3595–3611;
75. N. A. Meanwell, J. Med. Chem. 2011, 54, 2529–2591.
76. J. Atzrodt, V. Derdau, J. Labelled Compd. Radiopharm. 2010, 53, 674–685.
77. J. Atzrodt, V. Derdau, W. J. Kerr, M. Reid, Angew. Chem. Int. Ed. 2017, DOI: https://doi.org/10.1002/anie.201704146; Angew. Chem. 2017, DOI: https://doi.org/10.1002/ange.201704146.
78. L. Zhou, X. Bian, S. Yang, B. Mu, J. Labelled Compd. Radiopharm. 2012, 55, 158–160;
79. M. Macková, M. Himl, L. Minarova, J. Lang, P. Lhotak, Tetrahedron Lett. 2011, 52, 2543–2546;
80. U. Hakala, K. Waehaelae, J. Org. Chem. 2007, 72, 5817–5819;
81. A. Martins, M. Lautens, Org. Lett. 2008, 10, 4351–4353.
82. K. Müller, A. Seubert, Isot. Environ. Health Stud. 2014, 50, 88–93.
83. S. J. Rozze, M. J. Fray, J. Labelled Compd. Radiopharm. 2009, 52, 435–442;
84. F. Li, Q. Chen, C.-C. Liu, Y.-H. Wu, X.-P. Liu, G.-F. Yang, Appl. Magn. Reson. 2012, 42, 169–177;
85. N. Backstrom, C. I. F. Watt, Tetrahedron Lett. 2009, 50, 3234–3236;
86. J. R. Mohrig, N. J. Reiter, R. Kirk, M. R. Zawadski, V. N. Lamarre, J. Am. Chem. Soc. 2011, 133, 5124–5128.
87. X. Ariza, G. Asins, J. Garcia, F. G. Fausto, K. Makowski, D. Serra, J. Velasco, J. Labelled Compd. Radiopharm. 2010, 53, 556–558.
88. A. Miyazawa, H. Shimodaira, Y. Kawanishi, Bull. Chem. Soc. Jpn. 2011, 84, 1368–1370.
89. B. Kerler, J. Pol, K. Hartonen, M. T. Soederstroem, H. T. Koskela, M.-L. Riekkola, J. Supercrit. Fluids 2007, 39, 381–388.
90. L. Wang, Y. Murai, T. Yoshida, M. Okamoto, K. Masuda, Y. Sakihama, Y. Hashidoko, Y. Hatanaka, M. Hashimoto, Biosci. Biotechnol. Biochem. 2014, 78, 1129–1134.
91. Y. Murai, L. Wang, K. Masuda, Y. Sakihama, Y. Hashidoko, Y. Hatanaka, M. Hashimoto, Eur. J. Org. Chem. 2013, 5111–5116.
92. S. Duttwyler, A. M. Butterfield, J. S. Siegel, J. Org. Chem. 2013, 78, 2134–2138.
93. T. Sakamoto, K. Mori, T. Akiyama, Org. Lett. 2012, 14, 3312–3315.
94. D. Munz, M. Webster-Gardiner, R. Fu, T. Strassner, W. A. Goddard, T. B. Gunnoe, ACS Catal. 2015, 5, 769–775.
95. M. H. G. Prechtl, M. Teltewskoi, A. Dimitrov, E. Kemnitz, T. Braun, Chem. Eur. J. 2011, 17, 14385–14388.
96. D. W. Stephan, G. Erker, Angew. Chem. Int. Ed. 2015, 54, 6400–6441;
97. Angew. Chem. 2015, 127, 6498–6541.
98. M. Harhausen, R. Froehlich, G. Kehr, G. Erker, Organometallics 2012, 31, 2801–2809;
99. R. S. Chellappa, T. Autrey, M. Somayazulu, V. V. Struzhkin, R. J. Hemley, ChemPhysChem 2010, 11, 93–96;
100. C. Jiang, O. Blacque, T. Fox, H. Berke, Dalton Trans. 2011, 40, 1091–1097.
101. S. Tussing, L. Greb, S. Tamke, B. Schirmer, C. Muhle-Goll, B. Luy, J. Paradies, Chem. Eur. J. 2015, 21, 8056–8059.
102. A. Marek, M. H. F. Pedersen, Tetrahedron 2015, 71, 917–921.
103. Y. Hu, L. Liang, W. Wei, X. Sun, X. Zhang, M. Yan, Tetrahedron 2015, 71, 1425–1430.
104. K. Moozeh, S. M. So, J. Chin, Angew. Chem. Int. Ed. 2015, 54, 9381–9385;
105. Angew. Chem. 2015, 127, 9513–9517.
106. M. Zhan, R. Xu, Y. Tian, H. Jiang, L. Zhao, Y. Xie, Y. Chen, Eur. J. Org. Chem. 2015, 3370–3373.
107. H. Esaki, R. Ohtaki, T. Maegawa, Y. Monguchi, H. Sajiki, J. Org. Chem. 2007, 72, 2143–2150.
108. T. Kurita, F. Aoki, T. Mizumoto, T. Maejima, H. Esaki, T. Maegawa, Y. Monguchi, H. Sajiki, Chem. Eur. J. 2008, 14, 3371–3379.
109. V. Derdau, J. Atzrodt, Ger. Offen., DE 102005056856 A1, 2007;
110. V. Derdau, J. Atzrodt, W. Holla, J. Labelled Compd. Radiopharm. 2007, 50, 295–299.
111. J. Kang, A. Vonderheide, V. V. Guliants, ChemSusChem 2015, 8, 3044–3047.
112. V. P. Shevchenko, G. A. Badun, I. A. Razzhivina, I. Y. Nagaev, K. V. Shevchenko, N. F. Myasoedov, Dokl. Phys. Chem. 2015, 463, 182–187.
113. V. P. Shevchenko, I. A. Razzhivina, M. G. Chernysheva, G. A. Badun, I. Y. Nagaev, K. V. Shevchenko, N. F. Myasoedov, Radiochemistry 2015, 57, 312–320.
114. T. Kurita, K. Hattori, S. Seki, T. Mizumoto, F. Aoki, Y. Yamada, K. Ikawa, T. Maegawa, Y. Monguchi, H. Sajiki, Chem. Eur. J. 2008, 14, 664–673.
115. K. Hattori, H. Sajiki, K. Hirota, Tetrahedron 2000, 56, 8433–8441;
116. H. Sajiki, K. Hattori, K. Hirota, J. Org. Chem. 1998, 63, 7990;
117. H. Sajiki, K. Hattori, K. Hirota, J. Chem. Soc. Perkin Trans. 1 1998, 4043.
118. N. Modutlwa, H. Tada, Y. Sugahara, K. Shiraki, N. Hara, Y. Deyashiki, T. Ando, T. Maegawa, Y. Monguchi, H. Sajiki, Nucleic Acids Symp. Ser. 2009, 53, 105–106;
119. N. Modutlwa, H. Tada, Y. Sugahara, K. Shiraki, N. Hara, Y. Deyashiki, T. Maegawa, Y. Monguchi, H. Sajiki, Heterocycles 2012, 84, 419–429.
120. Y. Yabe, Y. Sawama, Y. Monguchi, H. Sajiki, Chem. Eur. J. 2013, 19, 484–488.
121. K. A. Guy, J. R. Shapley, Organometallics 2009, 28, 4020–4027.
122. Y. A. Zolotarev, A. K. Dadayan, Y. A. Borisov, V. S. Kozik, Chem. Rev. 2010, 110, 5425–5446.
123. G. V. Sidorov, N. F. Myasoedov, S. N. Lomin, G. A. Romanov, Radiochemistry 2015, 57, 108–110.
124. V. P. Shevchenko, I. Y. Nagaev, N. F. Myasoedov, Radiochemistry 2014, 56, 292–295.
125. V. P. Shevchenko, I. Y. Nagaev, K. V. Shevchenko, N. F. Myasoedov, Radiochemistry 2013, 55, 545–551.
126. Y. A. Zolotarev, A. K. Dadayan, V. S. Kozik, E. V. Gasanov, I. V. Nazimov, R. K. Ziganshin, B. V. Vaskovsky, A. N. Murashov, A. L. Ksenofontov, O. N. Kharybin, E. N. Nikolaev, N. F. Myasoedov, Russ. J. Bioorg. Chem. 2014, 40, 26–35.
127. G. E. E. Gardes, G. M. Pajonk, S. J. Teichner, J. Catal. 1974, 33, 145–148;
128. G. M. Psofogiannakis, G. E. Froudakis, J. Phys. Chem. C 2009, 113, 14908–14915;
129. R. Prins, Chem. Rev. 2012, 112, 2714–2738.
130. Y. A. Zolotarev, A. K. Dadayan, Y. A. Borisov, V. S. Kozik, I. V. Nazimov, R. H. Ziganshin, E. V. Bocharov, A. O. Chizhov, N. F. Myasoedov, J. Phys. Chem. C 2013, 117, 16878–16884.
131. V. P. Shevchenko, I. Y. Nagaev, K. V. Shevchenko, N. F. Myasoedov, Radiochemistry 2013, 55, 346–351.
132. V. P. Shevchenko, I. Y. Nagaev, N. F. Myasoedov, Dokl. Chem. 2013, 448, 66–67.
133. V. P. Shevchenko, Y. Nagaev, I. Yu, N. F. Myasoedov, Radiochemistry 2010, 52, 95–98.
134. Y. A. Zolotarev, Y. Y. Firsova, A. Abaimov, A. K. Dadayan, V. S. Kosik, A. V. Novikov, N. V. Krasnov, B. V. Vaskovskii, I. V. Nazimov, G. I. Kovalev, N. F. Myasoedov, Russ. J. Bioorg. Chem. 2009, 35, 296–305.
135. V. P. Shevchenko, I. Y. Nagaev, N. F. Myasoedov, Radiochemistry 2009, 51, 175–177.
136. A. A. Baitov, G. V. Sidorov, N. F. Myasoedov, Radiochemistry 2007, 49, 100–101.
137. V. P. Shevchenko, I. Y. Nagaev, G. A. Badun, M. G. Chernysheva, K. V. Shevchenko, N. F. Myasoedov, Dokl. Chem. 2012, 442, 42–46.
138. N. Ito, H. Esaki, T. Maesawa, E. Imamiya, T. Maegawa, H. Sajiki, Bull. Chem. Soc. Jpn. 2008, 81, 278–286.
139. Y. Sawama, T. Yamada, Y. Yabe, K. Morita, K. Shibata, M. Shigetsura, Y. Monguchi, H. Sajiki, Adv. Synth. Catal. 2013, 355, 1529–1534.
140. T. Kondo, T. Suzuki, J. Nakamura, J. Phys. Chem. Lett. 2011, 2, 577–580.
141. T. Maegawa, Y. Fujiwara, Y. Inagaki, H. Esaki, Y. Monguchi, H. Sajiki, Angew. Chem. Int. Ed. 2008, 47, 5394–5397;
142. Angew. Chem. 2008, 120, 5474–5477.
143. H. Sajiki, T. Maegawa, Y. Monguchi, WO 2008066158 A1, 2006.
144. T. Maegawa, Y. Fujiwara, Y. Inagaki, Y. Monguchi, H. Sajiki, Adv. Synth. Catal. 2008, 350, 2215–2218.
145. Y. Fujiwara, H. Iwata, Y. Sawama, Y. Monguchi, H. Sajiki, Chem. Commun. 2010, 46, 4977–4979.
146. Y. Sawama, Y. Yabe, H. Iwata, Y. Fujiwara, Y. Monguchi, H. Sajiki, Chem. Eur. J. 2012, 18, 16436–16442.
147. M. K. Gnanamani, W. D. Shafer, B. H. Davis, Catal. Lett. 2012, 142, 190–194.
148. M. K. Gnanamani, R. A. Keogh, W. D. Shafer, B. H. Davis, Appl. Catal. A 2011, 393, 130–137.
149. J. Roth, T. Schwarz-Selinger, V. K. Alimov, E. Markina, J. Nucl. Mater. 2013, 432, 341–347.
150. A. Rai, R. Schneider, A. Mutzke, M. Ravikant, Nucl. Instrum. Methods Phys. Res. Sect. B 2012, 291, 58–64.
151. H. Esaki, R. Ohtaki, T. Maegawa, T. Monguchi, H. Sajiki, J. Org. Chem. 2007, 72, 2143–2150.
152. N. Ito, T. Watahaki, T. Maesawa, T. Maegawa, H. Sajiki, Synthesis 2008, 1467–1478.
153. V. Derdau, J. Atzrodt, J. Zimmermann, C. Kroll, F. Brückner, Chem. Eur. J. 2009, 15, 10397–10404.
154. T. Maegawa, N. Ito, K. Oono, Y. Monguchi, H. Sajiki, Synthesis 2009, 2674–2678.
155. S. Bijani, V. Jain, D. Padmanabhan, B. Pandey, A. Shah, Tetrahedron Lett. 2015, 56, 1211–1214.
156. A. M. Krause-Heuer, N. R. Yepuri, T. A. Darwish, P. J. Holden, Molecules 2014, 19, 18604–18617;
157. H. Tsuji, C. Mitsui, E. Nakamura, Chem. Commun. 2014, 50, 14870–14872.
158. T. Yamada, Y. Sawama, K. Shibata, K. Morita, Y. Monguchi, H. Sajiki, RSC Adv. 2015, 5, 13727–13732.
159. S. Schou, J. Labelled Compd. Radiopharm. 2009, 52, 376–381.
160. For review on particles, see:
161. Nanoparticles and Catalysis, Vol. 1 (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2008;
162. The Nano-Micro Interface: Bridging the Micro and Nano Worlds (Eds.: M. Van de Voorde, M. Werner, H.-J. Fecht), Wiley-VCH, Weinheim, 2015.
163. J. A. Sullivan, K. A. Flanagan, H. Hain, Catal. Today 2008, 139, 154–160.
164. G. Pieters, C. Taglang, E. Bonnefille, T. Gutmann, C. Puente, J.-C. Berthet, C. Dugave, B. Chaudret, B. Rousseau, Angew. Chem. Int. Ed. 2014, 53, 230–234;
165. Angew. Chem. 2014, 126, 234–238.
166. C. Taglang, L. M. Martinez-Prieto, I. del Rosal, L. Maron, R. Poteau, K. Philippot, B. Chaudret, S. Perato, A. Sam Lone, C. Puente, C. Dugave, B. Rousseau, G. Pieters, Angew. Chem. Int. Ed. 2015, 54, 10474–10477;
167. Angew. Chem. 2015, 127, 10620–10623.
168. E. Bresó-Femenia, C. Godard, C. Claver, B. Chaudret, S. Castillón, Chem. Commun. 2015, 51, 16342–16345.
169. S. Bhatia, G. Spahlinger, N. Boukhumseen, Q. Boll, Z. Li, J. E. Jackson, Eur. J. Org. Chem. 2016, 4230–4235.
170. A. Di Giuseppe, R. Castarlenas, L. A. Oro, C. R. Chim. 2015, 18, 713–741.
171. W. J. S. Lockley, D. Hesk, J. Labelled Compd. Radiopharm. 2010, 53, 704–715.
172. G. N. Nilsson, W. J. Kerr, J. Labelled Compd. Radiopharm. 2010, 53, 662–667.
173. P. H. Allen, M. J. Hickey, L. P. Kingston, D. J. Wilkinson, J. Labelled Compd. Radiopharm. 2010, 53, 731–738.
174. W. J. S. Lockley, J. Labelled Compd. Radiopharm. 2010, 53, 668–673.
175. J. R. Heys, J. Labelled Compd. Radiopharm. 2007, 50, 770–778.
176. D. Hesk, P. McNamara, J. Labelled Compd. Radiopharm. 2007, 50, 875–887.
177. K. C. Westaway, J. Labelled Compd. Radiopharm. 2007, 50, 989–1005.
178. G. Parkin, J. Labelled Compd. Radiopharm. 2007, 50, 1088–1114.
179. E. M. Simmons, J. F. Hartwig, Angew. Chem. Int. Ed. 2012, 51, 3066–3072;
180. Angew. Chem. 2012, 124, 3120–3126.
181. M. Gómez-Gallego, M. A. Sierra, Chem. Rev. 2011, 111, 4857–4963;
182. G. C. Lloyd-Jones, M. P. Munoz, J. Labelled Compd. Radiopharm. 2007, 50, 1072–1087.
183. K. Swiderek, P. Paneth, Chem. Rev. 2013, 113, 7851–7879.
184. D. M. Heinekey, J. Labelled Compd. Radiopharm. 2007, 50, 1063–1071.
185. R. Bhattacharjee, A. Nijamudheen, S. Karmakar, A. Datta, Inorg. Chem. 2016, 55, 3023–3029.
186. O. Rivada-Wheelaghan, M. Rosello-Merino, M. A. Ortuno, P. Vidossich, E. Gutierrez-Puebla, A. Lledos, S. Conejero, Inorg. Chem. 2014, 53, 4257–4268.
187. M. Benedetti, C. R. Barone, C. R. Girelli, F. P. Fanizzi, G. Natile, L. Maresca, Dalton Trans. 2014, 43, 3669–3675.
188. S. K. Goforth, R. C. Walroth, L. McElwee-White, Inorg. Chem. 2013, 52, 5692–5701.
189. J. Campos, M. F. Espada, J. López-Serrano, E. Carmona, Inorg. Chem. 2013, 52, 6694–6704.
190. M. Grellier, S. A. Mason, A. Albinati, S. C. Capelli, S. Rizzato, C. Bijani, Y. Coppel, S. Sabo-Etienne, Inorg. Chem. 2013, 52, 7329–7337.
191. B. Butschke, S. G. Tabrizi, H. Schwarz, Chem. Eur. J. 2010, 16, 3962–3969.
192. S. H. Crosby, G. J. Clarkson, J. P. Rourke, J. Am. Chem. Soc. 2009, 131, 14142–14143.
193. B. Butschke, M. Schlangen, D. Schröder, H. Schwarz, Helv. Chim. Acta 2008, 91, 1902–1915.
194. S. M. Kloek, K. I. Goldberg, J. Am. Chem. Soc. 2007, 129, 3460–3461.
195. J. Garnett, R. Hodges, J. Am. Chem. Soc. 1967, 89, 4546–4547.
196. A. J. Hickman, J. M. Villalobos, M. S. Sanford, Organometallics 2009, 28, 5316–5322.
197. M. H. Emmert, J. B. Gary, J. M. Villalobos, M. S. Sanford, Angew. Chem. Int. Ed. 2010, 49, 5884–5886;
198. Angew. Chem. 2010, 122, 6020–6022.
199. J. M. Villalobos, A. J. Hickman, M. S. Sanford, Organometallics 2010, 29, 257–262.
200. A. J. Hickman, M. A. Cismesia, M. S. Sanford, Organometallics 2012, 31, 1761–1766.
201. M. S. Webster-Gardiner, R. Fu, G. C. Fortman, R. J. Nielsen, T. B. Gunnoe, W. A. Goddard III, Catal. Sci. Technol. 2015, 5, 96–100.
202. S. Ma, G. Villa, P. S. Thuy-Boun, A. Homs, J.-Q. Yu, Angew. Chem. Int. Ed. 2014, 53, 734–737;
203. Angew. Chem. 2014, 126, 753–756.
204. P. Hermange, A. T. Lindhardt, R. H. Taaning, K. Bjerglund, D. Lupp, T. Skrydstrup, J. Am. Chem. Soc. 2011, 133, 6061–6071.
205. S. Korsager, R. H. Taaning, A. T. Lindhardt, T. Skrydstrup, J. Org. Chem. 2013, 78, 6112–6120.
206. M. H. G. Prechtl, M. Hölscher, Y. Ben-David, N. Theyssen, R. Loschen, D. Milstein, W. Leitner, Angew. Chem. Int. Ed. 2007, 46, 2269–2272;
207. Angew. Chem. 2007, 119, 2319–2322.
208. S. H. Lee, S. I. Gorelsky, G. I. Nikonov, Organometallics 2013, 32, 6599–6604.
209. B. G. Hashiguchi, K. J. H. Young, M. Yousufuddin, W. A. Goddard, R. A. Periana, J. Am. Chem. Soc. 2010, 132, 12542–12545.
210. B. L. Conley, M. K. Pennington-Boggio, E. Boz, T. J. Williams, Chem. Rev. 2010, 110, 2294–2312.
211. L. Neubert, D. Michalik, S. Bähn, S. Imm, H. Neumann, J. Atzrodt, V. Derdau, W. Holla, M. Beller, J. Am. Chem. Soc. 2012, 134, 12239–12244.
212. B. Chatterjee, V. Krishnakumar, C. Gunanathan, Org. Lett. 2016, 18, 5892–5895.
213. L. V. A. Hale, N. K. Szymczak, J. Am. Chem. Soc. 2016, 138, 13489–13492.
214. W. Bai, K. H. Lee, S. K. S. Tse, K. W. Chan, Z. Lin, G. Jia, Organometallics 2015, 34, 3686–3698.
215. B. Gröll, M. Schnürch, M. D. Mihovilovic, J. Org. Chem. 2012, 77, 4432–4437.
216. A. Prades, M. Poyatos, E. Peris, Adv. Synth. Catal. 2010, 352, 1155–1162.
217. L. Piola, J. A. Fernández-Salas, S. Manzini, S. P. Nolan, Org. Biomol. Chem. 2014, 12, 8683–8688.
218. G. Erdogan, D. B. Grotjahn, J. Am. Chem. Soc. 2009, 131, 10354–10355.
219. S. K. S. Tse, P. Xue, Z. Lin, G. Jia, Adv. Synth. Catal. 2010, 352, 1512–1522.
220. C. P. Lenges, P. S. White, M. Brookhart, J. Am. Chem. Soc. 1999, 121, 4385–4396.
221. D. Hesk, J. R. Jones, W. J. S. Lockley, J. Labelled Compd. Radiopharm. 1990, 28, 1427–1436.
222. W. J. S. Lockley, J. Labelled Compd. Radiopharm. 1985, 22, 623–630.
223. W. J. S. Lockley, J. Labelled Compd. Radiopharm. 1984, 21, 45–57.
224. W. D. Jones, J. Feher, Organometallics 1983, 2, 562–563.
225. W. J. S. Lockley, Tetrahedron Lett. 1982, 23, 3819–3822.
226. M. Blake, J. Garnett, I. Gregor, J. Chem. Soc. Chem. Commun. 1975, 930–932.
227. S. Chen, G. Song, X. Li, Tetrahedron Lett. 2008, 49, 6929–6932.
228. J. L. Rhinehart, K. A. Manbeck, S. K. Buzak, G. M. Lippa, W. W. Brennessel, K. I. Goldberg, W. D. Jones, Organometallics 2012, 31, 1943–1952.
229. A. Di Giuseppe, R. Castarlenas, J. J. Pérez-Torrente, F. J. Lahoz, V. Polo, L. A. Oro, Angew. Chem. Int. Ed. 2011, 50, 3938–3942;
230. Angew. Chem. 2011, 123, 4024–4028.
231. A. Di Giuseppe, R. Castarlenas, J. J. Pérez-Torrente, F. J. Lahoz, L. A. Oro, Chem. Eur. J. 2014, 20, 8391–8403.
232. J. Campos, M. Rubio, A. C. Esqueda, E. Carmona, J. Labelled Compd. Radiopharm. 2012, 55, 29–38.
233. J. Campos, A. C. Esqueda, J. López-Serrano, L. Sánchez, F. P. Cossio, A. de Cozar, E. Alvarez, C. Maya, E. Carmona, J. Am. Chem. Soc. 2010, 132, 16765–16767.
234. E. M. Isin, C. S. Elmore, G. N. Nilsson, R. A. Thompson, L. Weidolf, Chem. Res. Toxicol. 2012, 25, 532–542.
235. J. M. Herbert, J. Labelled Compd. Radiopharm. 2010, 53, 658–661.
236. R. Salter, J. Labelled Compd. Radiopharm. 2010, 53, 645–657.
237. M. Perry, K. Burgess, Tetrahedron: Asymmetry 2003, 14, 951–961.
238. R. H. Crabtree, Acc. Chem. Res. 1979, 12, 331–337.
239. J. Verendel, O. Pàmies, M. Diéguez, P. G. Andersson, Chem. Rev. 2014, 114, 2130–2169.
240. G. C. Fortman, H. Jacobsen, L. Cavallo, S. P. Nolan, Chem. Commun. 2011, 47, 9723–9725.
241. V. M. Iluc, A. Fedorov, R. H. Grubbs, Organometallics 2012, 31, 39–41.
242. D. J. Nelson, J. D. Egbert, S. P. Nolan, Dalton Trans. 2013, 42, 4105–4109.
243. J. Zhou, J. F. Hartwig, Angew. Chem. Int. Ed. 2008, 47, 5783–5787;
244. Angew. Chem. 2008, 120, 5867–5871.
245. M. B. Skaddan, C. M. Yung, R. G. Bergman, Org. Lett. 2004, 6, 11–13.
246. S. K. Meier, K. J. H. Young, D. H. Ess, W. J. Tenn, J. Oxgaard, W. A. Goddard, R. A. Periana, Organometallics 2009, 28, 5293–5304.
247. Y. Feng, B. Jiang, P. A. Boyle, E. A. Ison, Organometallics 2010, 29, 2857–2867.
248. M. Lehman, J. Gary, P. Boyle, ACS Catal. 2013, 3, 2304–2310.
249. W. J. S. Lockley, J. Labelled Compd. Radiopharm. 2007, 50, 779–788.
250. R. Simonsson, G. Stenhagen, C. Ericsson, C. S. Elmore, J. Labelled Compd. Radiopharm. 2013, 56, 334–337.
251. J. R. Heys, C. S. Elmore, J. Labelled Compd. Radiopharm. 2009, 52, 189–200.
252. N. Bushby, D. A. Killick, J. Labelled Compd. Radiopharm. 2007, 50, 519–520.
253. S. Gruber, M. Neuburger, A. Pfaltz, Organometallics 2013, 32, 4702–4711.
254. M. L. J. Hickey, L. P. Kingston, W. J. S. Lockley, P. Allen, A. Mather, D. J. Wilkinson, J. Labelled Compd. Radiopharm. 2007, 50, 286–289.
255. H. M. Lee, T. Jiang, E. D. Stevens, S. P. Nolan, Organometallics 2001, 20, 1255–1258.
256. L. D. Vázquez-Serrano, B. T. Owens, J. M. Buriak, Chem. Commun. 2002, 2518–2519.
257. L. D. Vazquez-Serrano, B. T. Owens, J. M. Buriak, Inorg. Chim. Acta 2006, 359, 2786–2797.
258. M. E. Powell, C. S. Elmore, P. N. Dorff, J. R. Heys, J. Labelled Compd. Radiopharm. 2007, 50, 523–525.
259. P. W. C. Cross, J. M. Herbert, W. J. Kerr, A. H. McNeill, L. C. Paterson, Synlett 2016, 27, 111–115.
260. J. A. Brown, S. Irvine, A. R. Kennedy, W. J. Kerr, S. Andersson, G. N. Nilsson, Chem. Commun. 2008, 1115–1118.
261. J. A. Brown, A. R. Cochrane, S. Irvine, W. J. Kerr, B. Mondal, J. A. Parkinson, L. C. Paterson, M. Reid, T. Tuttle, S. Andersson, Adv. Synth. Catal. 2014, 356, 3551–3562.
262. A. R. Cochrane, C. Idziak, W. J. Kerr, B. Mondal, L. C. Paterson, T. Tuttle, S. Andersson, G. N. Nilsson, Org. Biomol. Chem. 2014, 12, 3598–3603.
263. A. Modvig, T. L. Andersen, R. H. Taaning, A. T. Lindhardt, T. Skrydstrup, J. Org. Chem. 2014, 79, 5861–5868.
264. J. Atzrodt, V. Derdau, W. J. Kerr, M. Reid, P. Rojahn, R. Weck, Tetrahedron 2015, 71, 1924–1929.
265. J. Devlin, W. J. Kerr, D. M. Lindsay, T. J. D. McCabe, M. Reid, T. Tuttle, Molecules 2015, 20, 11676–11698.
266. R. R. Naredla, C. Zheng, S. O. Nilsson Lill, D. A. Klumpp, J. Am. Chem. Soc. 2011, 133, 13169–13175.
267. W. J. Kerr, M. Reid, T. Tuttle, ACS Catal. 2015, 5, 402–410.
268. A. Shu, W. Chen, J. Heys, J. Organomet. Chem. 1996, 524, 87–93.
269. G. Ellames, J. Gibson, J. Herbert, A. McNeill, Tetrahedron 2001, 57, 9487–9497.
270. M. Parmentier, T. Hartung, A. Pfaltz, D. Muri, Chem. Eur. J. 2014, 20, 11496–11504.
271. A. R. Cochrane, S. Irvine, W. J. Kerr, M. Reid, S. Andersson, G. N. Nilsson, J. Labelled Compd. Radiopharm. 2013, 56, 451–454.
272. A. R. Kennedy, W. J. Kerr, R. Moir, M. Reid, Org. Biomol. Chem. 2014, 12, 7927–7931.
273. W. J. Kerr, D. M. Lindsay, M. Reid, J. Atzrodt, V. Derdau, P. Rojahn, R. Weck, Chem. Commun. 2016, 52, 6669–6672.
274. A. Burhop, R. Weck, J. Atzrodt, V. Derdau, Eur. J. Org. Chem. 2017, 1418–1424;
275. A. Burhop, R. Prohaska, R. Weck, J. Atzrodt, V. Derdau, J. Labelled Compd. Radiopharm. 2017, 60, 343–348.
276. K. Jess, V. Derdau, R. Weck, J. Atzrodt, M. Freytag, P. G. Jones, M. Tamm, Adv. Synth. Catal. 2017, 359, 629–638.
277. W. J. Kerr, M. Reid, T. Tuttle, Angew. Chem. Int. Ed. 2017, 56, 7808–7812;
278. Angew. Chem. 2017, 129, 7916–7920.
279. K. J. H. Young, O. A. Mironov, R. A. Periana, Organometallics 2007, 26, 2137–2140.
280. M. Hatano, T. Nishimura, H. Yorimitsu, Org. Lett. 2016, 18, 3674–3677.
281. R. P. Yu, D. Hesk, N. Rivera, I. Pelczer, P. J. Chirik, Nature 2016, 529, 195–199.