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