Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 51, Pages 16347-16351Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201709280
Keywords
bioinspired catalysis; C-H oxidation; molecular recognition; regioselectivity; supramolecular chemistry
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Funding
- MINECO of Spain [CTQ2015-70795-P]
- Catalan DIUE (ICREA Academia award) [2014 SGR 862]
- MIUR
- PRIN [2010CX2TLM]
- Sapienza Universita di Roma (Ricerca Scientifica - Anno)
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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(sp(3))-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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