Modular Approaches to Diversified Soft Lewis Basic Complexants through Suzuki-Miyaura Cross-Coupling of Bromoheteroarenes with Organotrifluoroborates
Modular Approaches to Diversified Soft Lewis Basic Complexants through Suzuki-Miyaura Cross-Coupling of Bromoheteroarenes with Organotrifluoroborates
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DOI：
10.1021/acs.joc.5b02662
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发表时间：
2016-02-05
影响因子：
3.6
通讯作者：
Carrick, Jesse D.
中科院分区：
文献类型：
--
作者：
Chin, Ai Lin;Carrick, Jesse D.
由于能源生产和遗留废物而获得的乏核燃料的补救或转化仍然是一个重大的环境问题。在过去的三十年里，实质性的努力集中在两相溶剂体系中，软-Lewis碱性络合剂在化学选择性地分离三价鳗系元素和稀土元素方面的潜力。该实验室最近的工作集中在模块化的概念上，以收敛的方式快速制备通过传统线性方法不易获得的络合剂和络合剂支架，以更好地了解过程相关溶剂中的溶解度和络合结构/活性函数。本工作描述了一种通过溴代杂芳烃与有机三氟硼酸盐的多Suzuki-Miyaura交叉偶联来构建多种络合剂的有效方法，在同一支架上以43-99%的产率获得了22种新材料，而不是两次、三次或四次交叉偶联。本文报道了催化剂/配体体系的优化、应用及局限性。
Remediation or transmutation of spent nuclear fuel obtained as a function of energy production and legacy waste remains a significant environmental concern. Substantive efforts over the last three decades have focused on the potential of soft-Lewis basic complexants for the chemoselective separation of trivalent actinides from lanthanides in biphasic solvent systems. Recent efforts in this laboratory have focused on the concept of modularity to rapidly prepare complexants and complexant scaffolds not easily accessible via traditional linear methods in a convergent manner to better understand solubility and complexation structure/activity function in process-relevant solvents. The current work describes an efficient method for the construction of diversified complexants through multi-Suzuki-Miyaura cross-coupling of bromoheteroarenes with organotrifluoroborates affording efficient access to 22 novel materials in 43-99% yield over two, three, or four cross-couplings on the same scaffold. Optimization of the catalyst/ligand system, application, and limitations are reported herein.