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78. Ellames GJ, Gibson JS, Herbert JM et al (2004) Ligand effects upon deuterium exchange in
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+ BF 4
À . J Label Compd Radiopharm 47:1–10. https://doi.
org/10.1002/jlcr.790
79. Herbert JM (2005) The mediation of aryl ketone deuteration by [Ir(PPh 3 ) 3 (cod)]BF 4 . J Label
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80. Habraken E, Haspeslagh P, Vliegen M, Noël T (2015) Iridium(I)-catalyzed ortho-directed
hydrogen isotope exchange in continuous-flow reactors. J Flow Chem 5:2–5. https://doi.org/
10.1556/JFC-D-14-00033
81. Herbert JM, Kohler AD, McNeill AH (2005) An improved bidentate complex of iridium as a
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org/10.1002/jlcr.921
82. Shu AYL, Chen W, Heys JR (1996) Organoiridium catalyzed hydrogen isotope exchange:
ligand effects on catalyst activity and regioselectivity. J Organomet Chem 524:87–93. https://
doi.org/10.1016/S0022-328X(96)06413-3
83. Ellames GJ, Gibson JS, Herbert JM et al (2001) Deuterium exchange mediated by an iridium–
phosphine complex formed in situ. Tetrahedron Lett 42:6413–6416. https://doi.org/10.1016/
S0040-4039(01)01266-7
84. Simonsson R, Stenhagen G, Ericsson C, Elmore CS (2013) Synthesis of ximelagatran,
melagatran, hydroxymelagatran, and ethylmelagatran in H-3 labeled form. J Label Compd
Radiopharm 56:334–337. https://doi.org/10.1002/jlcr.3028
85. Shu AYL, Heys JR (2000) Direct, efficient and selective tritiations of paclitaxel and
photoaffinity taxoids. Tetrahedron Lett 41:9015–9019. https://doi.org/10.1016/S0040-4039
(00)01652-X
86. Cross P, Herbert J, Kerr W et al (2015) Isotopic labelling of functionalised arenes catalysed by
iridium(I) species of the [(cod)Ir(NHC)(py)]PF 6 complex class. Synlett 27:111–115. https://
doi.org/10.1055/s-0035-1560518
87. Bushby N, Killick DA (2007) Hydrogen isotope exchange at alkyl positions using Crabtree’s
catalyst and its application to the tritiation of methapyrilene. J Label Compd Radiopharm
50:519–520. https://doi.org/10.1002/jlcr.1236
88. Ellames GJ, Gibson JS, Herbert JM, McNeill AH (2001) The scope and limitations of
deuteration mediated by Crabtree’s catalyst. Tetrahedron 57:9487–9497. https://doi.org/10.
1016/S0040-4020(01)00945-0
89. Valsborg JS, Sørensen L, Foged C (2001) Organoiridium catalysed hydrogen isotope
exchange of benzamide derivatives. J Label Compd Radiopharm 44:209–214. https://doi.
org/10.1002/jlcr.446
90. Kingston LP, Lockley WJS, Mather AN et al (2000) Parallel chemistry investigations of orthodirected hydrogen isotope exchange between substituted aromatics and isotopic water: novel
catalysis by cyclooctadienyliridium(I)pentan-1,3-dionates. Tetrahedron Lett 41:2705–2708.
https://doi.org/10.1016/S0040-4039(00)00244-6
91. McAuley B, Hickey MJ, Kingston LP et al (2003) Convenient and efficient deuteration of
functionalized aromatics with deuterium oxide: catalysis by cycloocta-1,5-dienyliridium
(I) 1,3-dionates. J Label Compd Radiopharm 46:1191–1204. https://doi.org/10.1002/jlcr.780
92. Jones JR, Lockley WJS, Lu S-Y, Thompson SP (2001) Microwave-enhanced aromatic
dehalogenation studies: a rapid deuterium-labelling procedure. Tetrahedron Lett
42:331–332. https://doi.org/10.1016/S0040-4039(00)01941-9
93. Gruber S, Neuburger M, Pfaltz A (2013) Characterization and reactivity studies of dinuclear
iridium hydride complexes prepared from iridium catalysts with N,P and C,N ligands under
hydrogenation conditions. Organometallics 32:4702–4711. https://doi.org/10.1021/
om4007467
298
M. Reid
using [Ir(COD)(Cy 3 P)(Py)]PF 6 as catalyst. J Label Compd Radiopharm 36:497–502. https://
doi.org/10.1039/C39920000680
78. Ellames GJ, Gibson JS, Herbert JM et al (2004) Ligand effects upon deuterium exchange in
arenes mediated by[Ir(PR 3 ) 2 (cod)]
+ BF 4
À . J Label Compd Radiopharm 47:1–10. https://doi.
org/10.1002/jlcr.790
79. Herbert JM (2005) The mediation of aryl ketone deuteration by [Ir(PPh 3 ) 3 (cod)]BF 4 . J Label
Compd Radiopharm 48:317–322. https://doi.org/10.1002/jlcr.925
80. Habraken E, Haspeslagh P, Vliegen M, Noël T (2015) Iridium(I)-catalyzed ortho-directed
hydrogen isotope exchange in continuous-flow reactors. J Flow Chem 5:2–5. https://doi.org/
10.1556/JFC-D-14-00033
81. Herbert JM, Kohler AD, McNeill AH (2005) An improved bidentate complex of iridium as a
catalyst for hydrogen isotope exchange. J Label Compd Radiopharm 48:285–294. https://doi.
org/10.1002/jlcr.921
82. Shu AYL, Chen W, Heys JR (1996) Organoiridium catalyzed hydrogen isotope exchange:
ligand effects on catalyst activity and regioselectivity. J Organomet Chem 524:87–93. https://
doi.org/10.1016/S0022-328X(96)06413-3
83. Ellames GJ, Gibson JS, Herbert JM et al (2001) Deuterium exchange mediated by an iridium–
phosphine complex formed in situ. Tetrahedron Lett 42:6413–6416. https://doi.org/10.1016/
S0040-4039(01)01266-7
84. Simonsson R, Stenhagen G, Ericsson C, Elmore CS (2013) Synthesis of ximelagatran,
melagatran, hydroxymelagatran, and ethylmelagatran in H-3 labeled form. J Label Compd
Radiopharm 56:334–337. https://doi.org/10.1002/jlcr.3028
85. Shu AYL, Heys JR (2000) Direct, efficient and selective tritiations of paclitaxel and
photoaffinity taxoids. Tetrahedron Lett 41:9015–9019. https://doi.org/10.1016/S0040-4039
(00)01652-X
86. Cross P, Herbert J, Kerr W et al (2015) Isotopic labelling of functionalised arenes catalysed by
iridium(I) species of the [(cod)Ir(NHC)(py)]PF 6 complex class. Synlett 27:111–115. https://
doi.org/10.1055/s-0035-1560518
87. Bushby N, Killick DA (2007) Hydrogen isotope exchange at alkyl positions using Crabtree’s
catalyst and its application to the tritiation of methapyrilene. J Label Compd Radiopharm
50:519–520. https://doi.org/10.1002/jlcr.1236
88. Ellames GJ, Gibson JS, Herbert JM, McNeill AH (2001) The scope and limitations of
deuteration mediated by Crabtree’s catalyst. Tetrahedron 57:9487–9497. https://doi.org/10.
1016/S0040-4020(01)00945-0
89. Valsborg JS, Sørensen L, Foged C (2001) Organoiridium catalysed hydrogen isotope
exchange of benzamide derivatives. J Label Compd Radiopharm 44:209–214. https://doi.
org/10.1002/jlcr.446
90. Kingston LP, Lockley WJS, Mather AN et al (2000) Parallel chemistry investigations of orthodirected hydrogen isotope exchange between substituted aromatics and isotopic water: novel
catalysis by cyclooctadienyliridium(I)pentan-1,3-dionates. Tetrahedron Lett 41:2705–2708.
https://doi.org/10.1016/S0040-4039(00)00244-6
91. McAuley B, Hickey MJ, Kingston LP et al (2003) Convenient and efficient deuteration of
functionalized aromatics with deuterium oxide: catalysis by cycloocta-1,5-dienyliridium
(I) 1,3-dionates. J Label Compd Radiopharm 46:1191–1204. https://doi.org/10.1002/jlcr.780
92. Jones JR, Lockley WJS, Lu S-Y, Thompson SP (2001) Microwave-enhanced aromatic
dehalogenation studies: a rapid deuterium-labelling procedure. Tetrahedron Lett
42:331–332. https://doi.org/10.1016/S0040-4039(00)01941-9
93. Gruber S, Neuburger M, Pfaltz A (2013) Characterization and reactivity studies of dinuclear
iridium hydride complexes prepared from iridium catalysts with N,P and C,N ligands under
hydrogenation conditions. Organometallics 32:4702–4711. https://doi.org/10.1021/
om4007467
298
M. Reid