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Controlling Selectivity in Aliphatic C−H Oxidation through Supramolecular Recognition
Author(s) -
Vidal Diego,
Olivo Giorgio,
Costas Miquel
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704852
Subject(s) - supramolecular chemistry , selectivity , chemistry , molecular recognition , combinatorial chemistry , crystallography , organic chemistry , catalysis , molecule , crystal structure
Abstract Aliphatic C−H oxidation is the most straightforward approach to functionalize hydrocarbon skeletons. The main challenge of this reaction is the control of site selectivity, given the multiple C−H bonds present in any organic molecule. Natural enzymes elegantly solve this problem through the interplay of different interactions that geometrically orient the substrate to expose a single C−H bond to the active unit, thus overriding intrinsic reactivity patterns. A combination of molecular catalysts and supramolecular receptors can be a promising way to replicate such control. This strategy indeed unlocks hydroxylation of C−H bonds that are not accessible with conventional methodologies, in which the selectivity is dictated by the geometry of the substrate–receptor adduct. Herein, we review the reports of recognition‐driven C−H oxidation reactions and highlight the key design principles that inspired these works.