期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 19, 期 3, 页码 684-690出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob02421j
关键词
-
资金
- JSPS KAKENHI [JP19H02721, JP20J23499]
- JSPS
This study describes a highly enantioselective intramolecular hydroarylation reaction using C-H activation, catalyzed by an iridium catalyst and a chiral bisphosphine ligand. The carbonyl group of ketones serves as an effective directing group, allowing for efficient synthesis of chiral 3-substituted dihydrobenzofurans in high yields and enantioselectivity from readily available starting materials. The reaction showcases the potential for developing a more efficient and selective variant of the reaction.
Intramolecular hydroarylation via C-H activation is one of the most powerful methods to synthesize carbo- and heterocyclic compounds, whereas we still have room for developing a highly enantioselective variant of the reaction. Here we describe Ir-catalyzed enantioselective intramolecular hydroarylation of m-allyloxyphenyl ketones. The enantioselective cyclization was efficiently catalyzed by a cationic iridium complex coordinated with a conventional chiral bisphosphine ligand to give benzofurans in high yields with high enantioselectivity. A carbonyl group of ketones functioned as an effective directing group for the C-H activation. In terms of synthetic utility, we also achieved one-pot synthesis of chiral 3-substituted dihydrobenzofurans from readily available allylic carbonates and m-hydroxyacetophenones via sequential Pd-catalyzed allylic substitution and Ir-catalyzed intramolecular hydroarylation.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据