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MeO
2
C
N
N
CO
2
Me
polymer beads
23
(1 equiv) +
25
(1 equiv) +
26
(20 equiv)
27
polymer
27
AuCl(PPh
3
)
Pd(OAc)
2
polymer
NaBH
4
coacerate
wash
cross-link
PI(Au/Pd)-OC
diglyme
24
diglyme
diglyme
Et
2
O
Et
2
O
150 °C
O
O
y
x
z
H
H
H
OTMS
25
O
OH
4
O
O
H
x:y:z = 1:1:1
24
O
23
26
Scheme 7.12
Synthesis of heterogeneous bifunctional chiral catalyst PI(Au/Pd)-OC.
OH
O
28
PI-Au/Pd/OC (2 mol %)
AcOH (20 mol %)
F
+
CO
2
Bn
EtOH/H
2
O 1:1
O
2
(1 atm), 30 °C, 24 h
*
BnO
2
C
2
Bn
CO
2
Bn
F
29
30
80%
e.e. 91%
(7.6)
Ar
O
+
29
HN
OTMS
Au
Pd
Au
Pd
Au
Pd
polymer
Other multistep processes, including imination
27
(Equation 7.7) and
amidation
28
(Equation 7.8) of alcohols have been reported using PI-CB/
Au-Pd and PI-CB/Au-Co, respectively.
Ph
OH
PI/CB-Au/Pd (1.5 mol %)
NaOH (0.25 equiv)
31
Bn
(7.7)
+
Ph
N
THF/TFE 9:1
O
2
(1 atm), 30 °C, 12 h
33
, 92%
Ph
NH
2
32
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