Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 9, Pages 2670-2674Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812379
Keywords
chiral porphyrinoids; cobalt; ligand design; metalloradical catalysis; synthetic methods
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Funding
- NIH [R01-GM102554]
- NSF [CHE-1624216]
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Novel D-2-symmetric chiral amidoporphyrins with alkyl bridges across two chiral amide units on both sides of the porphyrin plane (designated HuPhyrin) have been effectively constructed in a modular fashion to permit variation of the bridge length. The Co-II complexes of HuPhyrin, [Co (HuPhyrin)], represent new-generation metalloradical catalysts where the metal-centered d-radical is situated inside a cavity-like ligand with a more rigid chiral environment and enhanced hydrogen-bonding capability. As demonstrated with cyclopropanation and aziridination as model reactions, the bridged [Co (HuPhyrin)] functions notably different from the open catalysts, exhibiting significant enhancement in both reactivity and stereoselectivity. Furthermore, the length of the distal alkyl bridge can have a remarkable influence on the catalytic properties.
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