Angewandte Chemie - International Edition p. 16347 - 16351 (2017)
Update date:2022-08-11
Topics:
Olivo, Giorgio
Farinelli, Giulio
Barbieri, Alessia
Lanzalunga, Osvaldo
Di Stefano, Stefano
Costas, Miquel
Site-selective C-H functionalization of aliphatic alkyl chains is a longstanding challenge in oxidation catalysis, given the comparable relative reactivity of the different methylenes. A supramolecular, bioinspired approach is described to address this challenge. A Mn complex able to catalyze C(sp3)-H hydroxylation with H2O2 is equipped with 18-benzocrown-6 ether receptors that bind ammonium substrates via hydrogen bonding. Reversible pre-association of protonated primary aliphatic amines with the crown ether selectively exposes remote positions (C8 and C9) to the oxidizing unit, resulting in a site-selective oxidation. Remarkably, such control of selectivity retains its efficiency for a whole series of linear amines, overriding the intrinsic reactivity of C- H bonds, no matter the chain length.
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