13
RSnBu 3
CuCl 2 or MnBr 2 (10 mol%)
I 2 , DMF or NMP,100 °C, 4-5 h
R R
R = Aryl, Alkenyl, Alkynyl
Scheme 2.3 Cu- and
Mn-catalyzed oxidative
homo-coupling of
organostannanes
RSnBu 3
Pd(OAc) 2 (10 mol%)
CuCl 2 , THF, 23 °C, 7 min - 3 h
R R
R = Aryl, Alkenyl, Alkynyl
ArB(OH) 2
Pd(PPh 3 ) 4 (10 mol%)
Cu(NO 3 ) 2 , NaOAc, EtOH, r.t., 8 h
Ar Ar
ArB(OH) 2
Pd(OAc) 2 (4.5 mol%)
AgNO 3 , Et 3 N
NaCl, grinding, 30 min
Ar Ar
R
Te
n
Bu
PdCl 2 (8 mol%)
AgOAc, Et 3 N, MeOH
Ultrasonic, 15-20 h
R
R
R = Aryl, Alkenyl, Alkyl, SiMe 3 , CH 2 OMe
Scheme 2.4 Pd-catalyzed oxidative homo-couplings of organostannanes, arylboronic acids, and
n-butyl alkynyltellurides
RB(OH) 2
CrCl 2 (5 mol%)
Ag 2 O, THF, 65 o C, 10-12 h
R R
R = Alkyl, Aryl
B(OH) 2
Ph
B(OH) 2
+
CrCl 2 (5 mol%)
Ag 2 O, THF, 65 o C Ph
Ph
+
81% (1:1.1)
Scheme 2.5 Cr-catalyzed oxidative homo-coupling of organoboronic acids
2 Transition Metal-Catalyzed Oxidative Coupling Involving Two Organometallic…