Prominent Ligand Types in Modern Cross-Coupling Reactions - New Trends in Cross-Coupling: Theory and Applications - page 65

Me

Br

CO 2 H

Pd(AmPhos) 2 Cl 2 (0.1 mol %)
K 3 PO 4

N N

Me

N N

Me O Me O

F F

IPA/H 2 O, 80 °C

(HO) 2 B CO 2 H

F F

93 % , 2.05 kg scale

Figure 2.58 Kilogram-scale Suzuki-Miyaura reaction using Pd(AmPhos) 2 Cl 2 .

Pd(AmPhos) 2 Cl 2
or
Pd(AmPhos) 2 (0.5 - 1.5 mol%)
Base

Ar R

ArX

or or

R

HeteroArX HetAr R

MeCN or DMF, 80 - 110 °C

X = Br or Cl

67 - 95 % Yield

Figure 2.59 Heck alkynylation reactions of aryl and heteroaryl halides using Pd/AmPhos complexes.