Advances in C–C and C–X Coupling Using Palladium–NHeterocyclic Carbene (Pd–NHC) Complexes - New Trends in Cross-Coupling: Theory and Applications - page 209

[Pd(NHC)(3-Cl-pyridinyl)Cl 2 ]
(0.025 mol%)

O

Cl

N

+

H N O

KOt Bu, toluene, ref lux

Scheme 4.62 Reactivity of [Pd(IPr*)(3-Cl-pyridinyl)Cl 2 ] 86) in comparison with
other [Pd(NHC)(3-Cl-pyridinyl)Cl 2 ] complexes. Adapted from Ref. 56.

Table 4.26 Chemoselective amination using [Pd(IPr*)(acac)Cl].

[Pd(IPr*)(acac)Cl] (85)
0.4 mol%

R''

X

R''

N

+ H N

R'

Cl

Cl

R' LiHMDS, 1,4-dioxane, 110°C

X=Br,I

Entry Choride Amine Product Yield (%)

Cl I

1 71

NH 2

Cl H

2 65

Cl N O

Cl Br

H NO

Cl Br

3 76

NH 2 Cl H

Cl Cl

H NO

4 67

Br N O

Cl H

N

Cl

N

5 90

Br