jo5b02662_si_001.pdf (7.53 MB)
Modular Approaches to Diversified Soft Lewis Basic Complexants through Suzuki–Miyaura Cross-Coupling of Bromoheteroarenes with Organotrifluoroborates
journal contribution
posted on 2016-02-04, 15:55 authored by Ai Lin Chin, Jesse D. CarrickRemediation 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.