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通过 Rh(III)-催化的 5-芳基吡嗪酮与炔烃的氧化环化反应合成π-扩展杂环。

Synthesis of π-Extended Heterocycles via Rh(III)-Catalyzed Oxidative Annulation of 5-Aryl Pyrazinones with Alkynes.

机构信息

School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.

Department of Chemistry, Sookmyung Women's University, Seoul 04310, Republic of Korea.

出版信息

J Org Chem. 2021 Dec 3;86(23):16349-16360. doi: 10.1021/acs.joc.1c01752. Epub 2021 Sep 30.

Abstract

The Rh(III)-catalyzed C-H functionalization and subsequent oxidative annulation between 5-aryl pyrazinones and internal alkynes are reported. This protocol provides facile access to a wide range of pyrazinone-linked naphthalenes via the C(sp)-H alkenylation and subsequent annulation. This transformation is characterized by mild conditions, simplicity, and excellent functional group compatibility. Notably, it is a first report of the utilization of pyrazinones as directing groups in C-H functionalization.

摘要

报道了 Rh(III)催化的 5-芳基吡嗪酮与内部炔烃之间的 C-H 功能化和随后的氧化环化反应。该方案通过 C(sp)-H 烯丙基化和随后的环化反应,提供了简便地合成各种吡嗪酮连接的萘的方法。该转化的特点是条件温和、操作简单、官能团兼容性好。值得注意的是,这是首次报道吡嗪酮作为 C-H 功能化中导向基团的应用。

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