9 Metal Nanoparticles for Hydrogen Isotope Exchange
287
Ir
PPh 3
PPh 3
3 D 2
-C
8 H 12D 4
Ir
S
S
D
D
PPh 3
PPh 3
S
Ir S
D
D
PPh 3
PPh 3
NMe 2
O
S
D Ir
H
PPh 3
PPh 3
NMe 2
O
D
H Ir
D
PPh 3
PPh 3
NMe 2
O
D
NMe 2
O
Ir S
D
H
PPh 3
PPh 3
NMe 2
O
NMe 2
O
S
S
Deuterium labeling position
S = Solvent
6
7
8
9
10
11
Fig. 9.6 Reaction mechanism proposed by Heys and co-workers for the Ir(III) catalyzed HIE of
amides and esters [34]
DG
DG
Ir
N
N
Mes
Mes
PR 3
D 2 , DCM, rt
DG=
O
Ph
O
NH 2
O
NEt 2
O
N
N N
NO 2
H
N
O
PF 6
Deuterium labeling position
PR 3 = PPh 3 Ia, PBn 3 Ib, PMe 2 Ph Ic, PMe 2 Ph Id, P(O-i-Pr) 3 Ie
Fig. 9.7 Supported directing group by the first generation of Kerr catalysts [35]