N
B
B
N
C 12 H 25
Mes
Me
Mes
Me
N
B
Me
Mes
C 12 H 25
N
NH
C 12 H 25
Me
N
C 12 H 25
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
1. MeLi then MeI
N
NH 2
C 12 H 25
Me
Br
Br
Br
Br
Br
N
Me
C 12 H 25
Br
Br
Br
Br
Br
I
+
Pd(dba) 2 (5 mol %)
dppf (5 mol %)
2. t-BuLi then MesB(OMe) 2
63
64
65
66
NaOt Bu, Toluene
100 °C
59%
Me
Fig. 14 Synthesis of Boron-Containing Fused Heterocycles via Pd-Catalyzed N-Arylation
C–N bond formed through
Pd-catalyzed N-arylation
N
N
N
N
Zn
N
N
N
N
N
N
N
N
Zn
N
H
67
N B
N
N
N
O
O
O
O
68
OMe
C–N bond formed through
Pd-catalyzed N-arylation
t-Bu
t-Bu
t-Bu
Fig. 15 Synthesis of
N-Arylated Porphryins via
Pd-Catalyzed Coupling
Reactions
Palladium-Catalyzed sp
2 C–N Bond Forming Reactions. . .
37