Mizoroki−Heck Type Reaction of Organoboron Reagents with Alkenes and Alkynes. A Pd(II)-Catalyzed Pathway with Cu(OAc)2 as an Oxidant
Organic Letters2001Vol. 3(21), pp. 3313–3316
Citations Over TimeTop 10% of 2001 papers
Xiaoli Du, Masahiro Suguro, Kazunori Hirabayashi, Atsunori Mori, Takashi Nishikata, Nobuhito Hagiwara, Kentaro Kawata, Takeaki Okeda, Hui Wang, Keigo Fugami, Masanori Kosugi
Abstract
[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.
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