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γ-hydroxybutyric acid by heavy isotopes of hydrogen: iridium complex-mediated H/D
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Radiopharm 59:476–483. https://doi.org/10.1002/jlcr.3432
138. Zhou J, Hartwig JF (2008) Iridium-catalyzed H/D exchange at vinyl groups without olefin
isomerization. Angew Chem Int Ed 47:5783–5787. https://doi.org/10.1002/anie.200801992
139. Hatano M, Nishimura T, Yorimitsu H (2016) Selective H/D exchange at vinyl and
methylidene groups with D 2 O catalyzed by an iridium complex. Org Lett 18:3674–3677.
https://doi.org/10.1021/acs.orglett.6b01721
140. Spletstoser JT, White JM, Georg GI (2004) One-step facile synthesis of deuterium labeled
aldehydes from tertiary amides using Cp 2 Zr(D)Cl. Tetrahedron Lett 45:2787–2789. https://
doi.org/10.1016/j.tetlet.2004.02.030
141. Ariza X, Asins G, Garcia J et al (2010) Preparation of α-labeled aldehydes by base-catalyzed
exchange reactions. J Label Compd Radiopharm 53:556–558. https://doi.org/10.1002/jlcr.
1759
142. Chappelle MR, Hawes CR (2010) The use of metal-catalysed hydrogen isotope exchange in
the contract supply of tritiated compounds. J Label Compd Radiopharm 53:745–751. https://
doi.org/10.1002/jlcr.1821
143. Barnett DW, Refaei MS, Curley RW (2013) Chirally deuterated benzyl chlorides from benzyl
alcohols via hexachloroacetone/polymer-supported triphenylphosphine: synthesis of protected
(2 S , 3 S )-[32
H,
15
N]-tyrosine. J Label Compd Radiopharm 56:6–11. https://doi.org/10.
1002/jlcr.3004
Iridium Catalysts for Hydrogen Isotope Exchange
301
pharmaceutical compounds. Science 358:1182–1187. https://doi.org/10.1126/science.
aap9674
129. Golden JT, Andersen RA, Bergman RG (2001) Exceptionally low-temperature
carbonÀhydrogen/carbonÀdeuterium exchange reactions of organic and organometallic compounds catalyzed by the Cp*(PMe 3 )IrH(ClCH 2 Cl)
+ cation. J Am Chem Soc 123:5837–5838.
https://doi.org/10.1021/ja0155480
130. Klei SR, Golden JT, Burger P, Bergman RG (2002) Cationic Ir(III) alkyl and hydride
complexes: stoichiometric and catalytic C–H activation by CpÃ(PMe 3 )Ir(R)(X) in homogeneous solution. J Mol Catal A Chem 189:79–94. https://doi.org/10.1016/S1381-1169(02)
00192-9
131. Skaddan MB, Yung CM, Bergman RG (2004) Stoichiometric and catalytic deuterium and
tritium labeling of “Unactivated” organic substrates with cationic Ir(III) complexes. Org Lett
6:11–13. https://doi.org/10.1021/ol0359923
132. Corberán R, Sanaú M, Peris E (2006) Highly stable Cp*ÀIr(III) complexes with N -heterocyclic carbene ligands as CÀH activation catalysts for the deuteration of organic molecules. J
Am Chem Soc 128:3974–3979. https://doi.org/10.1021/ja058253l
133. Maishal TK, Alauzun J, Basset JM et al (2008) A tailored organometallic-inorganic hybrid
mesostructured material: a route to a well-defined, active, and reusable heterogeneous iridiumNHC catalyst for H/D exchange. Angew Chem Int Ed 47:8654–8656. https://doi.org/10.1002/
anie.200802956
134. Feng Y, Jiang B, Boyle PA, Ison EA (2010) Effect of ancillary ligands and solvents on H/D
exchange reactions catalyzed by Cp*Ir complexes. Organometallics 29:2857–2867. https://
doi.org/10.1021/om100018x
135. Lehman MC, Gary JB, Boyle PD et al (2013) Effect of solvent and ancillary ligands on the
catalytic H/D exchange reactivity of Cp IrIII(L) complexes. ACS Catal 3:2304–2310. https://
doi.org/10.1021/cs400420n
136. Romanenko I, Norsic S, Veyre L et al (2016) Active and recyclable polyethylene-supported
iridium-(N- heterocyclic carbene) catalyst for hydrogen/deuterium exchange reactions. Adv
Synth Catal 358:2317–2323. https://doi.org/10.1002/adsc.201600045
137. Marek A, Pedersen MHF, Vogensen SB et al (2016) The labeling of unsaturated
γ-hydroxybutyric acid by heavy isotopes of hydrogen: iridium complex-mediated H/D
exchange by C─H bond activation vs reduction by boro-deuterides/tritides. J Label Compd
Radiopharm 59:476–483. https://doi.org/10.1002/jlcr.3432
138. Zhou J, Hartwig JF (2008) Iridium-catalyzed H/D exchange at vinyl groups without olefin
isomerization. Angew Chem Int Ed 47:5783–5787. https://doi.org/10.1002/anie.200801992
139. Hatano M, Nishimura T, Yorimitsu H (2016) Selective H/D exchange at vinyl and
methylidene groups with D 2 O catalyzed by an iridium complex. Org Lett 18:3674–3677.
https://doi.org/10.1021/acs.orglett.6b01721
140. Spletstoser JT, White JM, Georg GI (2004) One-step facile synthesis of deuterium labeled
aldehydes from tertiary amides using Cp 2 Zr(D)Cl. Tetrahedron Lett 45:2787–2789. https://
doi.org/10.1016/j.tetlet.2004.02.030
141. Ariza X, Asins G, Garcia J et al (2010) Preparation of α-labeled aldehydes by base-catalyzed
exchange reactions. J Label Compd Radiopharm 53:556–558. https://doi.org/10.1002/jlcr.
1759
142. Chappelle MR, Hawes CR (2010) The use of metal-catalysed hydrogen isotope exchange in
the contract supply of tritiated compounds. J Label Compd Radiopharm 53:745–751. https://
doi.org/10.1002/jlcr.1821
143. Barnett DW, Refaei MS, Curley RW (2013) Chirally deuterated benzyl chlorides from benzyl
alcohols via hexachloroacetone/polymer-supported triphenylphosphine: synthesis of protected
(2 S , 3 S )-[32
H,
15
N]-tyrosine. J Label Compd Radiopharm 56:6–11. https://doi.org/10.
1002/jlcr.3004
Iridium Catalysts for Hydrogen Isotope Exchange
301