Gold-Catalyzed Domino Synthesis of Functionalized Benzofurans and Tetracyclic Isochromans via Formal Carboalkoxylation

作者:Obata Tomoyuki; Suzuki Sho; Nakagawa Asuka; Kajihara Ryota; Noguchi Keiichi; Saito Akio*
来源:Organic Letters, 2016, 18(16): 4136-4139.
DOI:10.1021/acs.orglett.6b02159

摘要

A domino synthesis of benzofurans with the modification of side chains from alpha-alkoxyalkyl o-alkynylaryl ethers (n = 0) and electron-rich arenes has been developed. In the present domino reaction, which would proceed via the alpha-alkoxyalkylation of arenes with an intermediate in the migratory cycloisomerization of o-alkynylaryl ethers followed by the nucleophilic addition of benzofurans to benzyl ethers, a cationic Au(III) catalyst activates the C-C pi bond and the C-O sigma bond. The present method could be extended to Au(I)-catalyzed domino synthesis of tetracyclit isochromans from alpha-alkoxyalkyl (o-alkynylaryl)methyl ethers (n = 1) and aryl methoxyrnethyl ethers.

  • 出版日期2016-8-19