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Modular Approaches to Diversified Soft Lewis Basic Complexants through Suzuki–Miyaura Cross-Coupling of Bromoheteroarenes with Organotrifluoroborates

By Ai Lin Chin (1393162) and Jesse D. Carrick (818517)

Abstract

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

Topics: Biochemistry, Cell Biology, Biotechnology, Space Science, Environmental Sciences not elsewhere classified, Biological Sciences not elsewhere classified, Mathematical Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, Physical Sciences not elsewhere classified, trivalent actinides, Lewis Basic Complexants, energy production, Substantive efforts, method, function, 22 novel materials, Modular Approaches, complexant scaffolds, legacy waste, Recent efforts, chemoselective separation, convergent manner
Year: 2016
DOI identifier: 10.1021/acs.joc.5b02662.s001
OAI identifier: oai:figshare.com:article/2071255
Provided by: FigShare
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