94. Vazquez-Serrano LD, Owens BT, Buriak JM (2006) The search for new hydrogenation
catalyst motifs based on N-heterocyclic carbene ligands. Inorg Chim Acta 359:2786–2797.
https://doi.org/10.1016/j.ica.2005.10.049
95. Powell ME, Elmore CS, Dorff PN, Heys JR (2007) Investigation of isotopic exchange
reactions using N-heterocyclic iridium (I) complexes. J Label Compd Radiopharm
50:523–525. https://doi.org/10.1002/jlcr.1239
96. Cross PWC, Ellames GJ, Gibson JS et al (2003) Conditions for deuterium exchange mediated
by iridium complexes formed in situ. Tetrahedron 59:3349–3358. https://doi.org/10.1016/
S0040-4020(03)00422-8
97. Brown JA, Irvine S, Kennedy AR et al (2008) Highly active iridium(i) complexes for catalytic
hydrogen isotope exchange. Chem Commun 1115. https://doi.org/10.1039/b715938b
98. Brown JA, Cochrane AR, Irvine S et al (2014) The synthesis of highly active iridium
(I) complexes and their application in catalytic hydrogen isotope exchange. Adv Synth Catal
356:3551–3562. https://doi.org/10.1002/adsc.201400730
99. Kerr WJ, Mudd RJ, Paterson LC, Brown JA (2014) Iridium(I)-catalyzed regioselective C–H
activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality. Chem A
Eur J 20:14604–14607. https://doi.org/10.1002/chem.201405114
100. Cochrane ARX, Idziak C, Kerr WJ et al (2014) Practically convenient and industrially-aligned
methods for iridium-catalysed hydrogen isotope exchange processes. Org Biomol Chem
12:3598–3603. https://doi.org/10.1039/C4OB00465E
101. Simmons EM, Hartwig JF (2012) On the interpretation of deuterium kinetic isotope effects in
C-H bond functionalizations by transition-metal complexes. Angew Chem Int Ed
51:3066–3072. https://doi.org/10.1002/anie.201107334
102. Kerr WJ, Reid M, Tuttle T (2015) Iridium-catalyzed C–H activation and deuteration of
primary sulfonamides: an experimental and computational study. ACS Catal 5:402–410.
https://doi.org/10.1021/cs5015755
103. Devlin J, Kerr W, Lindsay D et al (2015) Iridium-catalysed ortho-directed deuterium labelling
of aromatic esters – an experimental and theoretical study on directing group
Chemoselectivity. Molecules 20:11676–11698. https://doi.org/10.3390/molecules200711676
104. Kennedy AR, Kerr WJ, Moir R, Reid M (2014) Anion effects to deliver enhanced iridium
catalysts for hydrogen isotope exchange processes. Org Biomol Chem 12:7927–7931. https://
doi.org/10.1039/C4OB01570C
105. Queen AE, Hesk D, Lindsay DM et al (2020) Synthesis of [
3
H] and [
14
C]genipin. J Label
Compd Radiopharm 63:196–202. https://doi.org/10.1002/jlcr.3832
106. Kerr WJ, Lindsay DM, Reid M et al (2016) Iridium-catalysed ortho-H/D and -H/T exchange
under basic conditions: C–H activation of unprotected tetrazoles. Chem Commun
52:6669–6672. https://doi.org/10.1039/C6CC02137A
107. Atzrodt J, Derdau V, Kerr WJ et al (2015) Expanded applicability of iridium(I) NHC/phosphine catalysts in hydrogen isotope exchange processes with pharmaceutically-relevant heterocycles. Tetrahedron 71:1924–1929. https://doi.org/10.1016/j.tet.2015.02.029
108. Kerr WJ, Lindsay DM, Owens PK et al (2017) Site-selective deuteration of N -heterocycles via
iridium-catalyzed hydrogen isotope exchange. ACS Catal 7:7182–7186. https://doi.org/10.
1021/acscatal.7b02682
109. Kerr WJ, Mudd RJ, Owens PK et al (2016) Hydrogen isotope exchange with highly active
iridium(I) NHC/phosphine complexes: a comparative counterion study. J Label Compd
Radiopharm 59:601–603. https://doi.org/10.1002/jlcr.3427
110. Koneczny M, Phong Ho L, Nasr A et al (2020) Iridium(I) complexes with anionic
N-heterocyclic carbene ligands as catalysts for H/D exchange in nonpolar media. Adv Synth
Catal. https://doi.org/10.1002/adsc.202000438
111. Parmentier M, Hartung T, Pfaltz A, Muri D (2014) Iridium-catalyzed H/D exchange: ligand
complexes with improved efficiency and scope. Chem A Eur J 20:11496–11504. https://doi.
org/10.1002/chem.201402078
Iridium Catalysts for Hydrogen Isotope Exchange
299
catalyst motifs based on N-heterocyclic carbene ligands. Inorg Chim Acta 359:2786–2797.
https://doi.org/10.1016/j.ica.2005.10.049
95. Powell ME, Elmore CS, Dorff PN, Heys JR (2007) Investigation of isotopic exchange
reactions using N-heterocyclic iridium (I) complexes. J Label Compd Radiopharm
50:523–525. https://doi.org/10.1002/jlcr.1239
96. Cross PWC, Ellames GJ, Gibson JS et al (2003) Conditions for deuterium exchange mediated
by iridium complexes formed in situ. Tetrahedron 59:3349–3358. https://doi.org/10.1016/
S0040-4020(03)00422-8
97. Brown JA, Irvine S, Kennedy AR et al (2008) Highly active iridium(i) complexes for catalytic
hydrogen isotope exchange. Chem Commun 1115. https://doi.org/10.1039/b715938b
98. Brown JA, Cochrane AR, Irvine S et al (2014) The synthesis of highly active iridium
(I) complexes and their application in catalytic hydrogen isotope exchange. Adv Synth Catal
356:3551–3562. https://doi.org/10.1002/adsc.201400730
99. Kerr WJ, Mudd RJ, Paterson LC, Brown JA (2014) Iridium(I)-catalyzed regioselective C–H
activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality. Chem A
Eur J 20:14604–14607. https://doi.org/10.1002/chem.201405114
100. Cochrane ARX, Idziak C, Kerr WJ et al (2014) Practically convenient and industrially-aligned
methods for iridium-catalysed hydrogen isotope exchange processes. Org Biomol Chem
12:3598–3603. https://doi.org/10.1039/C4OB00465E
101. Simmons EM, Hartwig JF (2012) On the interpretation of deuterium kinetic isotope effects in
C-H bond functionalizations by transition-metal complexes. Angew Chem Int Ed
51:3066–3072. https://doi.org/10.1002/anie.201107334
102. Kerr WJ, Reid M, Tuttle T (2015) Iridium-catalyzed C–H activation and deuteration of
primary sulfonamides: an experimental and computational study. ACS Catal 5:402–410.
https://doi.org/10.1021/cs5015755
103. Devlin J, Kerr W, Lindsay D et al (2015) Iridium-catalysed ortho-directed deuterium labelling
of aromatic esters – an experimental and theoretical study on directing group
Chemoselectivity. Molecules 20:11676–11698. https://doi.org/10.3390/molecules200711676
104. Kennedy AR, Kerr WJ, Moir R, Reid M (2014) Anion effects to deliver enhanced iridium
catalysts for hydrogen isotope exchange processes. Org Biomol Chem 12:7927–7931. https://
doi.org/10.1039/C4OB01570C
105. Queen AE, Hesk D, Lindsay DM et al (2020) Synthesis of [
3
H] and [
14
C]genipin. J Label
Compd Radiopharm 63:196–202. https://doi.org/10.1002/jlcr.3832
106. Kerr WJ, Lindsay DM, Reid M et al (2016) Iridium-catalysed ortho-H/D and -H/T exchange
under basic conditions: C–H activation of unprotected tetrazoles. Chem Commun
52:6669–6672. https://doi.org/10.1039/C6CC02137A
107. Atzrodt J, Derdau V, Kerr WJ et al (2015) Expanded applicability of iridium(I) NHC/phosphine catalysts in hydrogen isotope exchange processes with pharmaceutically-relevant heterocycles. Tetrahedron 71:1924–1929. https://doi.org/10.1016/j.tet.2015.02.029
108. Kerr WJ, Lindsay DM, Owens PK et al (2017) Site-selective deuteration of N -heterocycles via
iridium-catalyzed hydrogen isotope exchange. ACS Catal 7:7182–7186. https://doi.org/10.
1021/acscatal.7b02682
109. Kerr WJ, Mudd RJ, Owens PK et al (2016) Hydrogen isotope exchange with highly active
iridium(I) NHC/phosphine complexes: a comparative counterion study. J Label Compd
Radiopharm 59:601–603. https://doi.org/10.1002/jlcr.3427
110. Koneczny M, Phong Ho L, Nasr A et al (2020) Iridium(I) complexes with anionic
N-heterocyclic carbene ligands as catalysts for H/D exchange in nonpolar media. Adv Synth
Catal. https://doi.org/10.1002/adsc.202000438
111. Parmentier M, Hartung T, Pfaltz A, Muri D (2014) Iridium-catalyzed H/D exchange: ligand
complexes with improved efficiency and scope. Chem A Eur J 20:11496–11504. https://doi.
org/10.1002/chem.201402078
Iridium Catalysts for Hydrogen Isotope Exchange
299