Chemistry Reference
In-Depth Information
cat. CuI / ligand
base, solvent, 110 °C
ArX
+
ROH
ArOR
Ar
X
R
Ligand
Base
Solvent
Yield (%)
C
6
H
5
Br
(CH
2
)
2
CH=CH
2
31
K
3
PO
4
Neat
92
C
6
H
5
Br
n
-C
4
H
9
31
K
3
PO
4
Neat
87
p
-PhC
6
H
4
Br
n
-C
4
H
9
31
K
3
PO
4
Neat
81
p
-CH
3
OC
6
H
4
Br
n
-C
4
H
9
n
31
K
3
PO
4
Neat
78
-C
4
H
9
n
p
-NO
2
C
6
H
4
Br
31
K
3
PO
4
Neat
83
-C
4
H
9
p
-AcC
6
H
4
Br
31
K
3
PO
4
Neat
92
3-Pyridyl
I
i
Pr
27
Cs
2
CO
3
Toluene
92
p
-CH
3
OC
6
H
4
I
i
Pr
Cs
2
CO
3
Toluene
79
27
p
-CH
3
OC
6
H
4
I
27
Cs
2
CO
3
Toluene
86
p
-CH
3
OC
6
H
4
I
cyclo-
5
H
9
27
Cs
2
CO
3
Toluene
75
3,5-(CH
3
)
2
C
6
H
4
I
cyclo-
5
H
9
27
Cs
2
CO
3
Toluene
67
Scheme 6.11
5mol%CuI
5mol%
OH
31
n
R
2
n
R
1
R
2
R
1
Cs
2
CO
3
, toluene, 110 °C
O
R
X
R
R
1
R
2
R
X
n
Yield (%)
H
Br
1
H
H
82
H
Br
1
CH
3
CH
3
83
H
Cl
1
H
H
82
H
Br
2
H
H
93
CH
3
Br
2
H
H
87
Scheme 6.12
6.3.4 Intramolecular Copper-Catalyzed Cross-Coupling
Reactions of Aryl Halides With Aliphatic Alcohols
Few examples exist for the copper-catalyzed intramolecular etherification
reaction of aryl halides and alcohols (Scheme 6.12).
56
Although the scope of
this chemistry is limited, five- and six-membered cyclic ethers have been
formed in good yields using copper iodide as catalyst in combination with
the hydroxyquinoline ligand 31.
6.4 Palladium-Catalyzed Cross-Coupling Reactions of
Carbon-Sulfur Bonds
The development of transition metal catalysts for carbon-sulfur bond for-
mation between aryl halides and aryl or alkyl thiols has produced fewer
catalysts than the corresponding carbon-oxygen bond formations. One of
the main reasons for fewer catalysts being developed for carbon-sulfur bond
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