Chemistry Reference
In-Depth Information
Table 4.2 Examples from the optimized (neocuproine)Pd(OAc)
2
system
from Ref. 154.
d
n
4
r
4
n
g
|
2
N
N
Pd
AcO
OAc
OH
O
R
R'
R
R'
DMSO:water (1:1)
NaOAc, 100
o
C
O
2
:N
2
(8:92) (50 b ar)
TOF
0
(h
-1
)
Time (h)
Substrate
Conversion (selectivity) (%)
OH
2
>500
100 (100)
OH
99 (99)
b
2
>500
OH
93 (>99)
c
3
400
.
95 (96)
d
3
400
OH
OH
3
300
80 (>99)
2.5
200
40 (75)
e
OH
5
OH
10
135
88 (>99)
OH
3
>330
100 (100)
MeO
a
Reaction conditions: 0.1 mol% (neocuproine)Pd(OAc)
2
, 20 mmol alcohol, 50 mL
water-DMSO 1:1 (v/v), 5 mol% NaOAc, 100 °C, 50 bar 8% O
2
/N
2
, 750 rpm stirring
speed.
b
Side-product 1-phenyl-1-buten-3-one.
c
Side-product cyclooctenone.
d
Side-
products 1-hydroxy-3-octanone (2%) and 3-octanone (1%).
e
Selectivity to heptanoic
acid, side products heptanal (20%), 2-heptenal (5%), 60 bar 8% O
2
/N
2
, Pd
0
formed.
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