9 Metal Nanoparticles for Hydrogen Isotope Exchange
301
29. Maguire JJ, Kuc RE, Davenport AP (2012) Radioligand binding assays and their analysis.
Methods Mol Biol 897:31–77
30. Harrell AW, Sychterz C, Ho MY, Weber A, Valko K, Negash K (2015) Interrogating the
relationship between rat in vivo tissue distribution and drug property data for > 200 structurally
unrelated molecules. Pharmacol Res Perspect 3. e00173/00171-e00173/00112
31. Voges R, Heys JR, Moenius T (2009) Preparation of compounds labeled with tritium and
carbon-14
32. Uttamsingh V, Gallegos R, Liu JF, Harbeson SL, Bridson GW, Cheng C, Wells DS, Graham PB,
Zelle R, Tung R (2015) Altering metabolic profiles of drugs by precision deuteration: reducing
mechanism-based inhibition of CYP2D6 by paroxetine. J Pharmacol Exp Ther 354:43–54
33. Crabtree R (1979) Iridium compounds in catalysis. Acc Chem Res 12:331–337
34. Heys R (1992) Investigation of iridium hydride complex [IrH2(Me2CO)2(PPh3)2]BF4 as a
catalyst of hydrogen isotope exchange of substrates in solution. J Chem Soc Chem Commun,
680–681
35. Brown JA, Irvine S, Kennedy AR, Kerr WJ, Andersson S, Nilsson GN (2008) Highly active
iridium(I) complexes for catalytic hydrogen isotope exchange. Chem Commun, 1115–1117
36. Atzrodt J, Derdau V, Kerr WJ, Reid M, Rojahn P, Weck R (2015) Expanded applicability of iridium(I) NHC/phosphine catalysts in hydrogen isotope exchange processes with
pharmaceutically-relevant heterocycles. Tetrahedron 71:1924–1929
37. Valero M, Weck R, Guessregen S, Atzrodt J, Derdau V (2018) Highly selective directed
iridium-catalyzed hydrogen isotope exchange reactions of aliphatic amides. Angew Chem
Int Ed 57:8159–8163
38. Kerr WJ, Mudd RJ, Reid M, Atzrodt J, Derdau V (2018) Iridium-catalyzed Csp3-H activation
for mild and selective hydrogen isotope exchange. ACS Catal 8:10895–10900
39. Cochrane AR, Irvine S, Kerr WJ, Reid M, Andersson S, Nilsson GN (2013) Application
of neutral iridium(I) N-heterocyclic carbene complexes in ortho-directed hydrogen isotope
exchange. J Labell Compd Radiopharm 56:451–454
40. 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
41. Kerr WJ, Reid M, Tuttle T (2017) Iridium-catalyzed formyl-selective deuteration of aldehydes.
Angew Chem Int Ed 56:7808–7812
42. Prechtl MHG, Hoelscher M, Ben-David Y, Theyssen N, Loschen R, Milstein D, Leitner W
(2007) H/D exchange at aromatic and heteroaromatic hydrocarbons using D2O as the deuterium
source and ruthenium dihydrogen complexes as the catalyst. Angew Chem Int Ed 46:2269–2272
43. Hale LVA, Szymczak NK (2016) Stereoretentive deuteration of α-chiral amines with D 2 O. J
Am Chem Soc 138:13489–13492
44. Maegawa T, Fujiwara Y, Inagaki Y, Monguchi Y, Sajiki H (2008) A convenient and effective
method for the regioselective deuteration of alcohols. Adv Synth Catal 350:2215–2218
45. Fujiwara Y, Iwata H, Sawama Y, Monguchi Y, Sajiki H (2010) Method for regio-, chemo- and
stereoselective deuterium labeling of sugars based on ruthenium-catalyzed C-H bond activation.
Chem Commun 46:4977–4979
46. Gao L, Perato S, Garcia-Argote S, Taglang C, Martinez-Prieto LM, Chollet C, Buisson D-A,
Dauvois V, Lesot P, Chaudret B et al (2018) Ruthenium-catalyzed hydrogen isotope exchange
of C(sp3)-H bonds directed by a sulfur atom. Chem Commun 54:2986–2989
47. Ma S, Villa G, Thuy-Boun PS, Homs A, Yu J-Q (2014) Palladium-catalyzed ortho-selective CH deuteration of arenes: evidence for superior reactivity of weakly coordinated palladacycles.
Angew Chem Int Ed 53:734–737
48. Yang H, Dormer PG, Rivera NR, Hoover AJ (2018) Palladium(II)-mediated C-H tritiation of
complex pharmaceuticals. Angew Chem Int Ed 57:1883–1887
49. Maegawa T, Akashi A, Esaki H, Aoki F, Sajiki H, Hirota K (2005) Efficient and selective
deuteration of phenylalanine derivatives catalyzed by Pd/C. Synlett, 845–847
50. Sajiki H, Esaki H, Aoki F, Maegawa T, Hirota K (2005) Palladium-catalyzed base-selective
H-D exchange reaction of nucleosides in deuterium oxide. Synlett, 1385–1388
301
29. Maguire JJ, Kuc RE, Davenport AP (2012) Radioligand binding assays and their analysis.
Methods Mol Biol 897:31–77
30. Harrell AW, Sychterz C, Ho MY, Weber A, Valko K, Negash K (2015) Interrogating the
relationship between rat in vivo tissue distribution and drug property data for > 200 structurally
unrelated molecules. Pharmacol Res Perspect 3. e00173/00171-e00173/00112
31. Voges R, Heys JR, Moenius T (2009) Preparation of compounds labeled with tritium and
carbon-14
32. Uttamsingh V, Gallegos R, Liu JF, Harbeson SL, Bridson GW, Cheng C, Wells DS, Graham PB,
Zelle R, Tung R (2015) Altering metabolic profiles of drugs by precision deuteration: reducing
mechanism-based inhibition of CYP2D6 by paroxetine. J Pharmacol Exp Ther 354:43–54
33. Crabtree R (1979) Iridium compounds in catalysis. Acc Chem Res 12:331–337
34. Heys R (1992) Investigation of iridium hydride complex [IrH2(Me2CO)2(PPh3)2]BF4 as a
catalyst of hydrogen isotope exchange of substrates in solution. J Chem Soc Chem Commun,
680–681
35. Brown JA, Irvine S, Kennedy AR, Kerr WJ, Andersson S, Nilsson GN (2008) Highly active
iridium(I) complexes for catalytic hydrogen isotope exchange. Chem Commun, 1115–1117
36. Atzrodt J, Derdau V, Kerr WJ, Reid M, Rojahn P, Weck R (2015) Expanded applicability of iridium(I) NHC/phosphine catalysts in hydrogen isotope exchange processes with
pharmaceutically-relevant heterocycles. Tetrahedron 71:1924–1929
37. Valero M, Weck R, Guessregen S, Atzrodt J, Derdau V (2018) Highly selective directed
iridium-catalyzed hydrogen isotope exchange reactions of aliphatic amides. Angew Chem
Int Ed 57:8159–8163
38. Kerr WJ, Mudd RJ, Reid M, Atzrodt J, Derdau V (2018) Iridium-catalyzed Csp3-H activation
for mild and selective hydrogen isotope exchange. ACS Catal 8:10895–10900
39. Cochrane AR, Irvine S, Kerr WJ, Reid M, Andersson S, Nilsson GN (2013) Application
of neutral iridium(I) N-heterocyclic carbene complexes in ortho-directed hydrogen isotope
exchange. J Labell Compd Radiopharm 56:451–454
40. 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
41. Kerr WJ, Reid M, Tuttle T (2017) Iridium-catalyzed formyl-selective deuteration of aldehydes.
Angew Chem Int Ed 56:7808–7812
42. Prechtl MHG, Hoelscher M, Ben-David Y, Theyssen N, Loschen R, Milstein D, Leitner W
(2007) H/D exchange at aromatic and heteroaromatic hydrocarbons using D2O as the deuterium
source and ruthenium dihydrogen complexes as the catalyst. Angew Chem Int Ed 46:2269–2272
43. Hale LVA, Szymczak NK (2016) Stereoretentive deuteration of α-chiral amines with D 2 O. J
Am Chem Soc 138:13489–13492
44. Maegawa T, Fujiwara Y, Inagaki Y, Monguchi Y, Sajiki H (2008) A convenient and effective
method for the regioselective deuteration of alcohols. Adv Synth Catal 350:2215–2218
45. Fujiwara Y, Iwata H, Sawama Y, Monguchi Y, Sajiki H (2010) Method for regio-, chemo- and
stereoselective deuterium labeling of sugars based on ruthenium-catalyzed C-H bond activation.
Chem Commun 46:4977–4979
46. Gao L, Perato S, Garcia-Argote S, Taglang C, Martinez-Prieto LM, Chollet C, Buisson D-A,
Dauvois V, Lesot P, Chaudret B et al (2018) Ruthenium-catalyzed hydrogen isotope exchange
of C(sp3)-H bonds directed by a sulfur atom. Chem Commun 54:2986–2989
47. Ma S, Villa G, Thuy-Boun PS, Homs A, Yu J-Q (2014) Palladium-catalyzed ortho-selective CH deuteration of arenes: evidence for superior reactivity of weakly coordinated palladacycles.
Angew Chem Int Ed 53:734–737
48. Yang H, Dormer PG, Rivera NR, Hoover AJ (2018) Palladium(II)-mediated C-H tritiation of
complex pharmaceuticals. Angew Chem Int Ed 57:1883–1887
49. Maegawa T, Akashi A, Esaki H, Aoki F, Sajiki H, Hirota K (2005) Efficient and selective
deuteration of phenylalanine derivatives catalyzed by Pd/C. Synlett, 845–847
50. Sajiki H, Esaki H, Aoki F, Maegawa T, Hirota K (2005) Palladium-catalyzed base-selective
H-D exchange reaction of nucleosides in deuterium oxide. Synlett, 1385–1388