1–6) and succinamide (Table 36, entries 7 and 8) under the generalized reaction
conditions to afford the corresponding N-aryl imides in good to excellent yields.
Similarly, aniline was subjected to cross coupling with substituted arylboronic
acids and o-, p-substituted anilines with phenylboronic acid, and the corresponding
N-aryl amines were obtained in satisfactory yields (Table 37, entries 1–9). The
coupling of alkylamines with phenylboronic acid gave the N-alkyl anilines in
moderate yields (Table 37, entries 10–14). However, the reaction of amides and
sulfonamides with phenylboronic acid afforded the corresponding products albeit in
lower yields (Table 37, entries 15 and 16).
Table 32 N-Arylation of aniline with various arylboronic acids
a
B(OH) 2
B(OH) 2
MeO
B(OH) 2
Me
B(OH) 2
B(OH) 2
Cl
B(OH) 2
F
B(OH) 2
F 3 C
B(OH) 2
Br
B(OH) 2
NO 2
1
2
3
4
3
4
4
3
93
90
87
5
6
7
3
8 7
3
8 9
4
9 0
8
9
2
6
7 9
Entry
Arylboronic acid
Time (h) Yield(%)
b
90
91
R
B(OH) 2
NH 2 CuFAP
H
N
rt, MeOH
+
R
Me
a Conditions: aniline (1.5 mmol), arylboronic acid (1 mmol), CuFAP (100 mg),
methanol (4 mL)
b
Isolated yields
Recent Developments in Recyclable Copper Catalyst Systems for C–N Bond. . .
159