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钯催化的 - 碳硼烷与芳烃之间BH/CH的分子内有氧氧化交叉偶联反应。

Palladium-catalyzed intramolecular aerobic oxidative cross-coupling of BH/CH between -carborane and arenes.

作者信息

Wang Zhen, Yu Jiahui, Zhang Jie, Zhang Dengsong, Qiu Zaozao, Xie Zuowei

机构信息

State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, School of Chemistry, and Chemical Engineering, Henan Normal University Xinxiang Henan 453007 China.

Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences Shanghai 200032 China

出版信息

Chem Sci. 2025 Jan 23;16(8):3705-3712. doi: 10.1039/d4sc08496a. eCollection 2025 Feb 19.

DOI:10.1039/d4sc08496a
PMID:39886433
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11775656/
Abstract

An efficient Pd-catalyzed regioselective intramolecular aerobic oxidative dehydrocoupling of BH/CH between -carborane and arenes has been achieved with the construction of a series of five-, six- and seven-membered rings under mild reaction conditions. Control experiments indicate that B-H activation proceeds preferentially over the aryl C-H. These new polyarene-carborane conjugates have potential applications in materials as demonstrated by pyrene fused -carborane that exhibits unique dual-phase emission, intramolecular charge transfer (ICT), and aggregation-induced emission (AIE) properties.

摘要

在温和的反应条件下,通过构建一系列五元、六元和七元环,实现了一种高效的钯催化的 - 碳硼烷与芳烃之间的BH/CH区域选择性分子内有氧氧化脱氢偶联反应。对照实验表明,B-H活化比芳基C-H活化更优先进行。这些新型的聚芳烃 - 碳硼烷共轭物在材料方面具有潜在应用,例如芘稠合的 - 碳硼烷表现出独特的双相发射、分子内电荷转移(ICT)和聚集诱导发光(AIE)特性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/75f0942f2502/d4sc08496a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/d3b6daa6db57/d4sc08496a-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/631ce94f814a/d4sc08496a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/75f0942f2502/d4sc08496a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/d3b6daa6db57/d4sc08496a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/84142caa0879/d4sc08496a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/4f8c2fc61d49/d4sc08496a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/ffaba38686a0/d4sc08496a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/0bcdee2e7e31/d4sc08496a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/8d0f4998c31a/d4sc08496a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/9c92f9d964df/d4sc08496a-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/28c535781399/d4sc08496a-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/631ce94f814a/d4sc08496a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fc87/11837271/75f0942f2502/d4sc08496a-f3.jpg

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本文引用的文献

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The Photosalient Effect and Thermochromic Luminescence Based on o-Carborane-Assisted π-Stacking in the Crystalline State.基于邻碳硼烷辅助π-堆积的晶态光突出效应和热致变色发光
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Ortho-Carborane Decorated Multi-Resonance TADF Emitters: Preserving Local Excited State and High Efficiency in OLEDs.
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