ol9b03170_si_002.pdf (22.44 MB)
Ni-Catalyzed Cycloisomerization between 3‑Phenoxy Acrylic Acid Derivatives and Alkynes via Intramolecular Cleavage and Formation of the C–O Bond To Give 2,3-Disubstituted Benzofurans
journal contribution
posted on 2019-09-30, 19:39 authored by Shohei Ohno, Jiawei Qiu, Ray Miyazaki, Hiroshi Aoyama, Kenichi Murai, Jun-ya Hasegawa, Mitsuhiro ArisawaReactions
based on transition-metal-catalyzed C–O bond cleavage
have attracted much attention as a new synthetic method. Until now,
several intermolecular reactions via C–O bond cleavage of aryl
ethers, alkenyl ethers, esters, and others have been reported. Here
we report an unprecedented C–O bond cleavage of 3-phenoxy acrylic
acid derivatives, followed by intramolecular C–O bond formation
with alkynes. This reaction gave 2,3-disubstituted benzofurans having
useful functional groupssilyl substituents and acrylic acid
derivativesat the 2- and 3-positions, respectively. This report
also described theoretical (DFT) insights into the mechanism.