Mizoroki−Heck Type Reaction of Organoboron Reagents with Alkenes and Alkynes. A Pd(II)-Catalyzed Pathway with Cu(OAc)2 as an Oxidant

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, an...

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Published inOrganic letters Vol. 3; no. 21; pp. 3313 - 3316
Main Authors Du, Xiaoli, Suguro, Masahiro, Hirabayashi, Kazunori, Mori, Atsunori, Nishikata, Takashi, Hagiwara, Nobuhito, Kawata, Kentaro, Okeda, Takeaki, Wang, Hui Feng, Fugami, Keigo, Kosugi, Masanori
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 18.10.2001
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Summary: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 β-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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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016529y