钯催化的非活化烯烃的氧化 Heck 反应，由氟化醇导向。
Palladium-catalyzed oxidative Heck reaction of non-activated alkenes directed by fluorinated alcohol.
机构信息
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China.
State Key Laboratory of Chemical Resource Engineering, Institute of Computational Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China.
出版信息
Chem Commun (Camb). 2022 Nov 15;58(91):12688-12691. doi: 10.1039/d2cc04921j.
A novel, Pd-catalyzed oxidative Heck reaction of non-activated alkenes synergistically directed by bifunctional groups has been developed firstly by using O as a green oxidant, yielding the oxidative Heck products with excellent yields in a regio- and stereoselective manner. This bifunctional synergistic activation mechanism was demonstrated by experimental analysis and detailed computational studies, wherein the hydroxyl group directs the migratory insertion of the alkenes and the trifluoromethyl group facilitates the subsequent β-H elimination and reductive elimination. Moreover, a pesticidal active compound was synthesized using the bifunctional synergistically directed C-H arylation as the key step, which demonstrated its synthetic utility.
首次发展了一种新型的 Pd 催化的非活化烯烃双功能协同导向的氧化 Heck 反应，以 O 为绿色氧化剂，以区域和立体选择性的方式得到了氧化 Heck 产物，产率优异。通过实验分析和详细的计算研究证明了这种双功能协同活化机制，其中羟基基团引导烯烃的迁移插入，三氟甲基基团促进随后的β-H 消除和还原消除。此外，使用双功能协同导向的 C-H 芳基化作为关键步骤合成了一种具有杀虫活性的化合物，证明了其合成实用性。
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