Chemistry Reference
In-Depth Information
Pd(OAc)
2
, (
R
)-BINAP
ArOTf
+
Ar
Proton Sponge™ (
1
)
O
O
benzene, 40 °C
Ar
Yield (%)
:
ee of
(%)
a
b
a
100
b
Ph
98 : 2
96
>
Ph
a
100
b
71 : 29
75
88
c
m
-ClC
6
H
4
72 : 28
96
>
78
c
o
-ClC
6
H
4
72 : 27
92
78
c
p
-NCC
6
H
4
66 : 34
96
>
a
Et
3
N was used instead of proton sponge.
b
Determined by GLC.
c
Isolated yield.
Table 8.10
Asymmetric intermolecular Heck reaction of vinyl triflate
Me
Me
Pd
2
(dba)
3
, ligand
OTf
Me
Me
O
+
base
benzene, 40 °C
O
ligand
base
yield (%)
ee (%)
Proton Sponge
TM
(
1
)
68
97
O
i
Pr
2
NEt
60
40
PPh
2
N
Et
3
N
26
38
t
Bu
Table 8.11
Asymmetric intramolecular Heck reaction of aryl triflate
O
O
Pd
2
(dba)
3
(5 mol%)
ligand (10 mol%)
Me
Me
N
N
OTf
4
base
toluene, 80 °C, 168 h
2
3
ligand
O
base
yield (%)
F
2,3
:F
3,4
ee (%)
N
t
Bu
Proton Sponge
TM
(
1
)
71
99 : 1
82
>
Fe
PPh
2
i
Pr
2
NEt
55
98 : 2
57
PMP
a
71
99 : 1
53
>
a
PMP
¼
1,2,2,6,6-pentamethylpiperidine.
