Mizoroki-Heck type reaction of organoboron reagents with alkenes and alkynes. A Pd(II)-catalyzed pathway with Cu(OAc)2 as an oxidant.
[reaction: see text]. In contrast to the Pd(0)-catalyzed mechanism by Uemura, Mizoroki-Heck type reaction of boronic acids is found to proceed under a Pd(II)-mediated pathway using a catalytic amount of Pd(OAc)2 in the presence of Cu(OAc)2 as an oxidant. Treatment of a variety of alkenes with boronic acids, boronates, and sodium tetraphenylborate furnishes beta-arylated and alkenylated products in good to excellent yields. The reactions with norbornene, norbornadiene, and diphenylacetylene are also performed to give 1:2 or 2:1 coupling products.
Du
X
X
Chemical Resources Laboratory, Tokyo Institute of Technology, Nagatsuta, Yokohama, Japan.
Suguro
M
M
Hirabayashi
K
K
Mori
A
A
Nishikata
T
T
Hagiwara
N
N
Kawata
K
K
Okeda
T
T
Wang
H F
HF
Fugami
K
K
Kosugi
M
M