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BuNI/tBuOOH 催化的 BODIPY 与烯丙基烯烃和醚的 α-区域选择性交叉脱氢偶联反应。

BuNI/tBuOOH catalyzed, α-regioselective cross-dehydrogenative coupling of BODIPY with allylic alkenes and ethers.

机构信息

The Key Laboratory of Functional Molecular Solids, Ministry of Education; School of Chemistry and Materials Science, Anhui Normal University, Wuhu, 241000, China.

Department of Chemistry, KU Leuven (Katholieke Universiteit Leuven), Celestijnenlaan 200f, 3001 Leuven, Belgium.

出版信息

Chem Commun (Camb). 2017 Jan 3;53(3):581-584. doi: 10.1039/c6cc08098g.

Abstract

A BuNI/tBuOOH-catalyzed, highly regioselective cross-dehydrogenative coupling (CDC) of the α-C-H bond(s) of the BODIPY core has been developed. The α-regioselective alkylation reaction utilizes easily accessible coupling partners, namely commercial allylic alkenes and ethers - even common, inert organic solvents, such as tetrahydrofuran, diethyl ether and 1,4-dioxane. The high α-regioselectivity of this CDC reaction is attributable to the radical process involved and provides a facile access to a variety of α-functionalized BODIPYs, which are hard to access through current synthetic methods.

摘要

发展了一种 BuNI/tBuOOH 催化的、高区域选择性的 BODIPY 核心的α-C-H 键(s)交叉脱氢偶联(CDC)反应。利用容易获得的偶联试剂,即商业烯丙基烯烃和醚,甚至是常见的惰性有机溶剂,如四氢呋喃、二乙醚和 1,4-二恶烷,实现了 α-区域选择性的烷基化反应。这种 CDC 反应的高α-区域选择性归因于涉及的自由基过程,为各种α-功能化的 BODIPY 提供了一种简便的合成途径,而这些 BODIPY 很难通过现有的合成方法获得。

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