Mizoroki-Heck type reaction of organoboron reagents with alkenes and alkynes. A Pd(II)-catalyzed pathway with Cu(OAc)2 as an oxidant

X Du; M Suguro; K Hirabayashi; A Mori; T Nishikata; N Hagiwara; K Kawata; T Okeda; H F Wang; K Fugami; M Kosugi

doi:10.1021/ol016529y

Mizoroki-Heck type reaction of organoboron reagents with alkenes and alkynes. A Pd(II)-catalyzed pathway with Cu(OAc)2 as an oxidant

Org Lett. 2001 Oct 18;3(21):3313-6. doi: 10.1021/ol016529y.

Authors

X Du¹, M Suguro, K Hirabayashi, A Mori, T Nishikata, N Hagiwara, K Kawata, T Okeda, H F Wang, K Fugami, M Kosugi

Affiliation

¹ Chemical Resources Laboratory, Tokyo Institute of Technology, Nagatsuta, Yokohama, Japan.

PMID: 11594822
DOI: 10.1021/ol016529y

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.