Phenanthroline-based metal–organic frameworks for Fe-catalyzed C sp3 –H amination

Thacker, Nathan C.; Ji, Pengfei; Lin, Zekai; Urban, Ania; Lin, Wenbin

doi:10.1039/C7FD00030H

Phenanthroline-based metal–organic frameworks for Fe-catalyzed C _sp3 –H amination

Journal Article · Sat Dec 31 23:00:00 EST 2016 · Faraday Discussions

DOI:https://doi.org/10.1039/C7FD00030H· OSTI ID:1393654

Thacker, Nathan C. ^[1]; Ji, Pengfei ^[1]; Lin, Zekai ^[1]; Urban, Ania ^[1]; Lin, Wenbin ^[1]

Department of Chemistry; University of Chicago; Chicago; USA

We report here the synthesis of a robust and highly porous Fe-phenanthroline-based metal–organic framework (MOF) and its application in catalyzing challenging inter- and intramolecular C–H amination reactions. For the intermolecular amination reactions, a FeBr₂-metalated MOF selectively functionalized secondary benzylic and allylic C–H bonds. The intramolecular amination reactions utilizing organic azides as the nitrene source required the reduction of the FeBr₂-metalated MOF with NaBHEt₃to generate the active catalyst. For both reactions, Fe or Zr leaching was less than 0.1%, and MOFs could be recycled and reused with no loss in catalytic activity. Furthermore, MOF catalysts were significantly more active than the corresponding homogeneous analogs. This work demonstrates the great potential of MOFs in generating highly active, recyclable, and reusable earth abundant metal catalysts for challenging organic transformations.

Research Organization:: Advanced Photon Source (APS), Argonne National Laboratory (ANL), Argonne, IL (US)

Sponsoring Organization:: NSF

OSTI ID:: 1393654

Journal Information:: Faraday Discussions, Journal Name: Faraday Discussions Journal Issue: 2017 Vol. 201; ISSN 1359-6640

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: ENGLISH

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