22. Lockley WJS (2010) Hydrogen isotope labelling using iridium(I) dionates. J Label Compd
Radiopharm 53:668–673. https://doi.org/10.1002/jlcr.1806
23. Gusev DG, Berke H (1996) Hydride fluxionality in Transition metal complexes: an approach
to the understanding of mechanistic features and structural diversities. Chem Ber
129:1143–1155. https://doi.org/10.1002/cber.19961291002
24. Elander N, Jones JR, Lu S-Y, Stone-Elander S (2000) Microwave-enhanced radiochemistry.
Chem Soc Rev 29:239–249. https://doi.org/10.1039/a901713e
25. Takeuchi R, Kezuka S (2006) Iridium-catalyzed formation of carbon-carbon and carbonheteroatom bonds. Synthesis (Stuttg) 2006:3349–3366. https://doi.org/10.1055/s-2006950284
26. Salter R (2010) The development and use of iridium(I) phosphine systems for ortho-directed
hydrogen-isotope exchange. J Label Compd Radiopharm 53:645–657. https://doi.org/10.
1002/jlcr.1814
27. Milstein D (2010) Discovery of environmentally benign catalytic reactions of alcohols catalyzed by pyridine-based pincer Ru complexes, based on metal–ligand cooperation. Top Catal
53:915–923. https://doi.org/10.1007/s11244-010-9523-7
28. Herbert JM (2010) Deuterium exchange promoted by iridium complexes formed in situ. J
Label Compd Radiopharm 53:658–661. https://doi.org/10.1002/jlcr.1790
29. Atzrodt J, Derdau V (2010) Pd- and Pt-catalyzed H/D exchange methods and their application
for internal MS standard preparation from a Sanofi-Aventis perspective. J Label Compd
Radiopharm 53:674–685. https://doi.org/10.1002/jlcr.1818
30. Wiegerinck P (2011) 17th workshop of the international isotope society – central European
division. The synthesis and applications of isotopes and isotopically labelled compounds. J
Label Compd Radiopharm 54:278–288. https://doi.org/10.1002/jlcr.1859
31. Choi J, MacArthur AHR, Brookhart M, Goldman AS (2011) Dehydrogenation and related
reactions catalyzed by iridium pincer complexes. Chem Rev 111:1761–1779. https://doi.org/
10.1021/cr1003503
32. Gregson TJ, Herbert JM, Row EC (2011) Synthetic approaches to regiospecifically mono- and
dilabelled arenes. J Label Compd Radiopharm 54:1–32. https://doi.org/10.1002/jlcr.1783
33. Suzuki T (2011) Organic synthesis involving iridium-catalyzed oxidation. Chem Rev
111:1825–1845. https://doi.org/10.1021/cr100378r
34. Aboagye EO, Aigbirhio FI, Allen P et al (2014) Abstracts of the 22nd international isotope
society (UK Group) symposium: synthesis and applications of labelled compounds 2013. J
Label Compd Radiopharm 57:178–190. https://doi.org/10.1002/jlcr.3173
35. Iglesias M, Oro LA (2018) A leap forward in iridium–NHC catalysis: new horizons and
mechanistic insights. Chem Soc Rev 47:2772–2808. https://doi.org/10.1039/C7CS00743D
36. Shevchenko VP, Nagaev IY, Myasoedov NF (2019) Effect of processes occurring in the
presence of metal catalysts on the main characteristics of the hydrogen isotope labeled organic
compounds obtained. Radiochemistry 61:257–292. https://doi.org/10.1134/
S1066362219030019
37. Lin D, Chang W (2000) Chemical derivatization and the selection of deuterated internal
standard for quantitative determination – methamphetamine example. J Anal Toxicol
24:275–280. https://doi.org/10.1093/jat/24.4.275
38. Heinekey DM (2007) Transition metal dihydrogen complexes: isotope effects on reactivity
and structure. J Label Compd Radiopharm 50:1063–1071. https://doi.org/10.1002/jlcr.1385
39. Lloyd-Jones GC, Muñoz MP (2007) Isotopic labelling in the study of organic and organometallic mechanism and structure: an account. J Label Compd Radiopharm 50:1072–1087.
https://doi.org/10.1002/jlcr.1382
40. Quasdorf KW, Huters AD, Lodewyk MW et al (2012) Total synthesis of oxidized
welwitindolinones and (À)- N -methylwelwitindolinone C isonitrile. J Am Chem Soc
134:1396–1399. https://doi.org/10.1021/ja210837b
Iridium Catalysts for Hydrogen Isotope Exchange
295
Radiopharm 53:668–673. https://doi.org/10.1002/jlcr.1806
23. Gusev DG, Berke H (1996) Hydride fluxionality in Transition metal complexes: an approach
to the understanding of mechanistic features and structural diversities. Chem Ber
129:1143–1155. https://doi.org/10.1002/cber.19961291002
24. Elander N, Jones JR, Lu S-Y, Stone-Elander S (2000) Microwave-enhanced radiochemistry.
Chem Soc Rev 29:239–249. https://doi.org/10.1039/a901713e
25. Takeuchi R, Kezuka S (2006) Iridium-catalyzed formation of carbon-carbon and carbonheteroatom bonds. Synthesis (Stuttg) 2006:3349–3366. https://doi.org/10.1055/s-2006950284
26. Salter R (2010) The development and use of iridium(I) phosphine systems for ortho-directed
hydrogen-isotope exchange. J Label Compd Radiopharm 53:645–657. https://doi.org/10.
1002/jlcr.1814
27. Milstein D (2010) Discovery of environmentally benign catalytic reactions of alcohols catalyzed by pyridine-based pincer Ru complexes, based on metal–ligand cooperation. Top Catal
53:915–923. https://doi.org/10.1007/s11244-010-9523-7
28. Herbert JM (2010) Deuterium exchange promoted by iridium complexes formed in situ. J
Label Compd Radiopharm 53:658–661. https://doi.org/10.1002/jlcr.1790
29. Atzrodt J, Derdau V (2010) Pd- and Pt-catalyzed H/D exchange methods and their application
for internal MS standard preparation from a Sanofi-Aventis perspective. J Label Compd
Radiopharm 53:674–685. https://doi.org/10.1002/jlcr.1818
30. Wiegerinck P (2011) 17th workshop of the international isotope society – central European
division. The synthesis and applications of isotopes and isotopically labelled compounds. J
Label Compd Radiopharm 54:278–288. https://doi.org/10.1002/jlcr.1859
31. Choi J, MacArthur AHR, Brookhart M, Goldman AS (2011) Dehydrogenation and related
reactions catalyzed by iridium pincer complexes. Chem Rev 111:1761–1779. https://doi.org/
10.1021/cr1003503
32. Gregson TJ, Herbert JM, Row EC (2011) Synthetic approaches to regiospecifically mono- and
dilabelled arenes. J Label Compd Radiopharm 54:1–32. https://doi.org/10.1002/jlcr.1783
33. Suzuki T (2011) Organic synthesis involving iridium-catalyzed oxidation. Chem Rev
111:1825–1845. https://doi.org/10.1021/cr100378r
34. Aboagye EO, Aigbirhio FI, Allen P et al (2014) Abstracts of the 22nd international isotope
society (UK Group) symposium: synthesis and applications of labelled compounds 2013. J
Label Compd Radiopharm 57:178–190. https://doi.org/10.1002/jlcr.3173
35. Iglesias M, Oro LA (2018) A leap forward in iridium–NHC catalysis: new horizons and
mechanistic insights. Chem Soc Rev 47:2772–2808. https://doi.org/10.1039/C7CS00743D
36. Shevchenko VP, Nagaev IY, Myasoedov NF (2019) Effect of processes occurring in the
presence of metal catalysts on the main characteristics of the hydrogen isotope labeled organic
compounds obtained. Radiochemistry 61:257–292. https://doi.org/10.1134/
S1066362219030019
37. Lin D, Chang W (2000) Chemical derivatization and the selection of deuterated internal
standard for quantitative determination – methamphetamine example. J Anal Toxicol
24:275–280. https://doi.org/10.1093/jat/24.4.275
38. Heinekey DM (2007) Transition metal dihydrogen complexes: isotope effects on reactivity
and structure. J Label Compd Radiopharm 50:1063–1071. https://doi.org/10.1002/jlcr.1385
39. Lloyd-Jones GC, Muñoz MP (2007) Isotopic labelling in the study of organic and organometallic mechanism and structure: an account. J Label Compd Radiopharm 50:1072–1087.
https://doi.org/10.1002/jlcr.1382
40. Quasdorf KW, Huters AD, Lodewyk MW et al (2012) Total synthesis of oxidized
welwitindolinones and (À)- N -methylwelwitindolinone C isonitrile. J Am Chem Soc
134:1396–1399. https://doi.org/10.1021/ja210837b
Iridium Catalysts for Hydrogen Isotope Exchange
295