Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 46, Pages 21030-21034Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c10778
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- US National Science Foundation [CHE-1954985]
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In this study, we successfully isolated a cyclometalated nickel(IV) complex that is similar to a key intermediate proposed in aminoquinoline-directed C-H functionalization catalysis. The complex undergoes bond-forming reaction under mild conditions and demonstrates the importance of LX-type ligands in stabilizing these nickel(IV) species.
We use a ligand design strategy to isolate a cyclometalated nickel(IV) complex that is directly analogous to a key intermediate proposed in aminoquinoline-directed C-H functionalization catalysis. This nickel(IV) complex is formed by oxidative addition of a diaryliodonium reagent to an anionic nickel(II)-picolinate precursor. The nickel(IV) sigma-aryl complex is stable at room temperature but undergoes C(sp(2))-C(sp(3)) bond-forming reductive elimination under mild conditions (70 degrees C, 120 min). Overall, this study demonstrates the accessibility of long-sought-after nickel(IV) intermediates in C-H functionalization catalysis. Furthermore, it demonstrates that LX-type (bidentate, mono-anionic) ligands such as picolinate dramatically stabilize these nickel(IV) species.
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