Chemistry Reference
In-Depth Information
cat. Pd
ArX
+
RSH
ArSR
additives, solvent
P
t
-Bu
2
Me
P
i
Pr
2
Br
PCy
2
Fe
t
-Bu
3
P
Pd
Pd
P
t
-Bu
3
Fe
Br
P
i
Pr
2
40
41
42
ArX
R
Pd
L
Additives
Solvent
Yield (%)
o
-CF
3
C
6
H
4
Br
C
6
H
5
40
-
t
Bu/
ZnCl
2
/LiI
THF
99
m
-CO
2
HC
6
H
4
Br
C
6
H
5
40
-
Bu/
ZnCl
2
/LiI
O
t
THF
77
o
-CH
3
OC
6
H
4
Br
t
-C
4
H
9
40
-
t
Bu/
ZnCl
2
/LiI
THF
84
2,6-(CH
3
)
2
C
6
H
3
Br
Bn
40
-
t
Bu/
ZnCl
2
/LiI
THF
99
p
-CH
3
OC
6
H
4
Br
t
-C
4
H
9
Pd(OAc)
2
41
NaO
t
Bu
Dioxane
99
2,5-(CH
3
)
2
C
6
H
3
Cl
t
-C
4
H
9
Pd(OAc)
2
41
NaO
t
Bu
Dioxane
95
p
-CH
3
OC
6
H
4
Cl
p-
CH
3
OC
6
H
5
Pd(OAc)
2
41
NaO
t
Bu
Dioxane
93
m
-CNC
6
H
4
Cl
C
6
H
5
Pd(OAc)
2
41
NaO
t
Bu
Dioxane
82
m
-NH
2
C(O)C
6
H
4
Cl
C
6
H
5
Pd(OAc)
2
NaO
t
Bu
DME
70
42
C
6
H
5
Cl
t
-C
4
H
9
Pd(OAc)
2
42
Cs
2
CO
3
DME
91
m
-CH
3
C
6
H
4
Cl
p
-CH
3
C
6
H
5
Pd(OAc)
2
42
LiHMDS
DME
93
o
-CH
3
OC
6
H
4
Cl
C
6
H
5
Pd(OAc)
2
42
KO
t
Bu
DME
97
Scheme 6.13
2.5 mol % Pd
2
dba
3
6 mol %
PPh
2
PPh
2
X
O
S
S
Cs
2
CO
3
, toluene, 100 °C
X = Br, 74% yield
X = Cl, 44% yield
Scheme 6.14
5 mol % Pd
2
dba
3
5.5 mol %
PtBu
2
Ph
Br
S
S
R
Cs
2
CO
3
, toluene, 100 °C
N
H
R
R = tBu, 88%
R = CH
3
, 77%
R = N(CH
3
)
2
, 90%
R = Ph, 100%
Scheme 6.15
Intramolecular reactions of aryl halides with thioamides are catalyzed by
palladium and a bulky, electron-rich monodentate phosphine ligand
(Scheme 6.15),
74
providing benzothiazoles in good yields. The identity of the
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