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Metal-organic layers stabilize earth-abundant metal-terpyridine diradical complexes for catalytic C-H activation.
Chemical Science 2018 January 8
We report the synthesis of a terpyridine-based metal-organic layer (TPY-MOL) and its metalation with CoCl2 and FeBr2 to afford CoCl2 ·TPY-MOL and FeBr2 ·TPY-MOL, respectively. Upon activation with NaEt3 BH, CoCl2 ·TPY-MOL catalyzed benzylic C-H borylation of methylarenes whereas FeBr2 ·TPY-MOL catalyzed intramolecular Csp3 -H amination of alkyl azides to afford pyrrolidines and piperidines. X-ray absorption near edge structure (XANES), extended X-ray absorption fine structure (EXAFS), X-ray photoelectron spectroscopy, UV-Vis-NIR spectroscopy, and electron paramagnetic spectroscopy (EPR) measurements as well as density functional theory (DFT) calculations identified M(THF)2 ·TPY-MOL (M = Co or Fe) as the active catalyst with a MII -(TPY˙˙)2- electronic structure featuring divalent metals and TPY diradical dianions. We believe that site isolation stabilizes novel MII -(TPY˙˙)2- (M = Co or Fe) species in the MOLs to endow them with unique and enhanced catalytic activities for Csp3 -H borylation and intramolecular amination over their homogeneous counterparts. The MOL catalysts are also superior to their metal-organic framework analogs owing to the removal of diffusion barriers. Our work highlights the potential of MOLs as a novel 2D molecular material platform for designing single-site solid catalysts without diffusional constraints.
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