59. Liu Y, Gridnev ID, Zhang W (2014) Mechanism of the asymmetric hydrogenation of
exocyclic α,β-unsaturated carbonyl compounds with an iridium/BiphPhox catalyst: NMR
and DFT studies. Angew Chem Int Ed 53:1901–1905. https://doi.org/10.1002/anie.
201309677
60. Polo V, Al-Saadi AA, Oro LA (2014) Theoretical studies on the mechanism of iridiumcatalyzed alkene hydrogenation by the cationic complex [IrH 2 (NCMe) 3 (PiPr 3 )]
+ . Organometallics 33:5156–5163. https://doi.org/10.1021/om500361e
61. Verendel JJ, Pàmies O, Diéguez M, Andersson PG (2014) Asymmetric hydrogenation of
olefins using chiral Crabtree-type catalysts: scope and limitations. Chem Rev 114:2130–2169.
https://doi.org/10.1021/cr400037u
62. Lee HM, Jiang T, Stevens ED, Nolan SP (2001) A cationic iridium complex bearing an
imidazol-2-ylidene ligand as alkene hydrogenation catalyst. Organometallics 20:1255–1258
63. Vázquez-Serrano LD, Owens BT, Buriak JM (2002) Catalytic olefin hydrogenation using
N-heterocyclic carbene–phosphine complexes of iridium. Chem Commun:2518
64. Perry M, Burgess K (2003) Chiral N-heterocyclic carbene-transition metal complexes in
asymmetric catalysis. Tetrahedron Asymm 14:951–961
65. Zhu S-F, Xie J-B, Zhang Y-Z et al (2006) Well-defined chiral spiro iridium/phosphineoxazoline cationic complexes for highly enantioselective hydrogenation of imines at ambient
pressure. J Am Chem Soc 128:12886–12891. https://doi.org/10.1021/ja063444p
66. Smidt SP, Pfaltz A, Martínez-Viviente E et al (2003) X-ray and NOE studies on trinuclear
iridium hydride phosphino oxazoline (PHOX) complexes. Organometallics 22:1000–1009.
https://doi.org/10.1021/om020805a
67. Vazquez-Serrano LD, Owens BT (2006) The search for new hydrogenation catalyst motifs
based on N-heterocyclic carbene ligands. Inorg Chim Acta 359:2786
68. Li S, Zhu S-F, Zhang C-M et al (2008) Iridium-catalyzed enantioselective hydrogenation of
alpha, beta-unsaturated carboxylic acids. J Am Chem Soc 130:8584–8585. https://doi.org/10.
1021/ja802399v
69. Garnett JL, Long MA, McLaren AB, Peterson KB (1973) Iridium(III) salts as homogeneous
metal catalysts for hydrogen isotope exchange in organic compounds: a comparison with
heterogeneous iridium for the deuteriation of alkylbenzenes. J Chem Soc Chem Commun
749:749. https://doi.org/10.1039/c39730000749
70. Vliegen M, Haspeslagh P, Verluyten W (2012) Alternative efficient tritium labeling of
repaglinide. J Label Compd Radiopharm 55:155–157. https://doi.org/10.1002/jlcr.2913
71. Hickey MJ, Kingston LP, Lockley WJS et al (2007) Tritium-labelling via an iridium-based
solid-phase catalyst. J Label Compd Radiopharm 50:286–289. https://doi.org/10.1002/jlcr.
1233
72. Heys JR, Shu AYL, Senderoff SG, Phillips NM (1993) Deuterium exchange labelling of
substituted aromatics using [IrH 2 (Me 2 CO) 2 (PPh 3 ) 2 ]BF 4 . J Label Compd Radiopharm
33:431–438. https://doi.org/10.1002/jlcr.2580330509
73. Lockley WJS (1985) Regioselective labelling of anilides with deuterium. J Label Compd
Radiopharm 22:623–630. https://doi.org/10.1002/jlcr.2580220612
74. Lockley WJS (1984) Regioselective deuterium labelling of aromatic acids, amides and amines
using group VIII metal catalysts. J Label Compd Radiopharm 21:45–57. https://doi.org/10.
1002/jlcr.2580210105
75. Hesk D, Jones JR, Lockley WJS (1990) Regiospecific tritium labeling of aromatic acids,
amides, amines and heterocyclics using homogeneous rhodium trichloride and ruthenium
acetylacetonate catalysts. J Label Compd Radiopharm 28:1427–1436. https://doi.org/10.
1002/jlcr.2580281211
76. Heys JR, Elmore CS (2009) Meta -substituent effects on organoiridium-catalyzed ortho
-hydrogen isotope exchange. J Label Compd Radiopharm 52:189–200. https://doi.org/10.
1002/jlcr.1588
Iridium Catalysts for Hydrogen Isotope Exchange
297
exocyclic α,β-unsaturated carbonyl compounds with an iridium/BiphPhox catalyst: NMR
and DFT studies. Angew Chem Int Ed 53:1901–1905. https://doi.org/10.1002/anie.
201309677
60. Polo V, Al-Saadi AA, Oro LA (2014) Theoretical studies on the mechanism of iridiumcatalyzed alkene hydrogenation by the cationic complex [IrH 2 (NCMe) 3 (PiPr 3 )]
+ . Organometallics 33:5156–5163. https://doi.org/10.1021/om500361e
61. Verendel JJ, Pàmies O, Diéguez M, Andersson PG (2014) Asymmetric hydrogenation of
olefins using chiral Crabtree-type catalysts: scope and limitations. Chem Rev 114:2130–2169.
https://doi.org/10.1021/cr400037u
62. Lee HM, Jiang T, Stevens ED, Nolan SP (2001) A cationic iridium complex bearing an
imidazol-2-ylidene ligand as alkene hydrogenation catalyst. Organometallics 20:1255–1258
63. Vázquez-Serrano LD, Owens BT, Buriak JM (2002) Catalytic olefin hydrogenation using
N-heterocyclic carbene–phosphine complexes of iridium. Chem Commun:2518
64. Perry M, Burgess K (2003) Chiral N-heterocyclic carbene-transition metal complexes in
asymmetric catalysis. Tetrahedron Asymm 14:951–961
65. Zhu S-F, Xie J-B, Zhang Y-Z et al (2006) Well-defined chiral spiro iridium/phosphineoxazoline cationic complexes for highly enantioselective hydrogenation of imines at ambient
pressure. J Am Chem Soc 128:12886–12891. https://doi.org/10.1021/ja063444p
66. Smidt SP, Pfaltz A, Martínez-Viviente E et al (2003) X-ray and NOE studies on trinuclear
iridium hydride phosphino oxazoline (PHOX) complexes. Organometallics 22:1000–1009.
https://doi.org/10.1021/om020805a
67. Vazquez-Serrano LD, Owens BT (2006) The search for new hydrogenation catalyst motifs
based on N-heterocyclic carbene ligands. Inorg Chim Acta 359:2786
68. Li S, Zhu S-F, Zhang C-M et al (2008) Iridium-catalyzed enantioselective hydrogenation of
alpha, beta-unsaturated carboxylic acids. J Am Chem Soc 130:8584–8585. https://doi.org/10.
1021/ja802399v
69. Garnett JL, Long MA, McLaren AB, Peterson KB (1973) Iridium(III) salts as homogeneous
metal catalysts for hydrogen isotope exchange in organic compounds: a comparison with
heterogeneous iridium for the deuteriation of alkylbenzenes. J Chem Soc Chem Commun
749:749. https://doi.org/10.1039/c39730000749
70. Vliegen M, Haspeslagh P, Verluyten W (2012) Alternative efficient tritium labeling of
repaglinide. J Label Compd Radiopharm 55:155–157. https://doi.org/10.1002/jlcr.2913
71. Hickey MJ, Kingston LP, Lockley WJS et al (2007) Tritium-labelling via an iridium-based
solid-phase catalyst. J Label Compd Radiopharm 50:286–289. https://doi.org/10.1002/jlcr.
1233
72. Heys JR, Shu AYL, Senderoff SG, Phillips NM (1993) Deuterium exchange labelling of
substituted aromatics using [IrH 2 (Me 2 CO) 2 (PPh 3 ) 2 ]BF 4 . J Label Compd Radiopharm
33:431–438. https://doi.org/10.1002/jlcr.2580330509
73. Lockley WJS (1985) Regioselective labelling of anilides with deuterium. J Label Compd
Radiopharm 22:623–630. https://doi.org/10.1002/jlcr.2580220612
74. Lockley WJS (1984) Regioselective deuterium labelling of aromatic acids, amides and amines
using group VIII metal catalysts. J Label Compd Radiopharm 21:45–57. https://doi.org/10.
1002/jlcr.2580210105
75. Hesk D, Jones JR, Lockley WJS (1990) Regiospecific tritium labeling of aromatic acids,
amides, amines and heterocyclics using homogeneous rhodium trichloride and ruthenium
acetylacetonate catalysts. J Label Compd Radiopharm 28:1427–1436. https://doi.org/10.
1002/jlcr.2580281211
76. Heys JR, Elmore CS (2009) Meta -substituent effects on organoiridium-catalyzed ortho
-hydrogen isotope exchange. J Label Compd Radiopharm 52:189–200. https://doi.org/10.
1002/jlcr.1588
Iridium Catalysts for Hydrogen Isotope Exchange
297