19
ArB(OH) 2
PdCl 2 (rac-BINAP) 2
(2.5 mol%)
PhCHBrCO 2 Me
(BrCH 2 CO 2 Et)
KF, dioxana/H 2 O
100 °C, 2-24 h
Ar
Ar
Scheme 2.19 Pd-catalyzed
oxidative homo-coupling of
arylboronic acids
RZnX
PdCl 2 (rac-BINAP) 2
(10 mol%)
PhCHBrCO 2 Me
(Desyl Bromide)
(Desyl Chloride)
THF, r.t. - 60 °C, 16 h
R R
O
Ph
Br
Ph
O
Ph
Cl
Ph
Desyl Bromide Desyl Chloride
Scheme 2.20 Pd-catalyzed oxidative homo-coupling of alkylzinc reagents
Si
Ph
Ph
Me
N
Me
N
SnBu 3
Et
Et
Si
Ph
Ph
Me
N
Me
N
SnBu 3
Et
Et
Bu 3 Sn
Si
Ph
Ph
Me
N
Me
N
Et
Et
N
Me
Si
N
Me
Ph
Ph
Et Et
Si
Ph
Ph
Me
N
Me
N
Et
Et
N
Me
Si
N
Me
Ph
Ph
Et Et
N
Me
Si
N
Me
Ph
Ph
Et Et
+
28%
17%
PdCl 2 (PPh 3 ) 2 (5 mol%)
MeCOCH 2 Cl, DMF/THF
50 °C, 20 h
+
Scheme 2.17 Pd-catalyzed oxidative coupling of arylstannanes
SnBu 3
PdCl 2 (PPh 3 ) 2 (10 mol%)
PhCHBrCO 2 Me
THF, r.t., 3 d
Ph
Ph
20%
Scheme 2.18 Pd-catalyzed oxidative homo-coupling of tributyl(phenylacetylenyl)tin
2 Transition Metal-Catalyzed Oxidative Coupling Involving Two Organometallic…