Anion‐π catalysis enabled by the mechanical bond

Maynard, J. R. J., Galmés, B., Stergiou, A. D., Symes, M. D. , Frontera, A. and Goldup, S. M. (2022) Anion‐π catalysis enabled by the mechanical bond. Angewandte Chemie (International Edition), 61(12), e202115961. (doi: 10.1002/anie.202115961) (PMID:35040543)

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We report a series of rotaxane-based anion–π catalysts in which the mechanical bond between a bipyridine macrocycle and an axle containing an NDI unit is intrinsic to the activity observed, including a [3]rotaxane that catalyses an otherwise disfavoured Michael addition in >60 fold selectivity over a competing decarboxylation pathway that dominates under Brønsted base conditions. The results are rationalized by detailed experimental investigations, electrochemical and computational analysis.

Item Type:Articles
Glasgow Author(s) Enlighten ID:Symes, Professor Mark and Stergiou, Mr Athanasios
Authors: Maynard, J. R. J., Galmés, B., Stergiou, A. D., Symes, M. D., Frontera, A., and Goldup, S. M.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Angewandte Chemie (International Edition)
ISSN (Online):1521-3773
Published Online:18 January 2022
Copyright Holders:Copyright © 2022 The Authors
First Published:First published in Angewandte Chemie (International Edition) 61(12): e202115961
Publisher Policy:Reproduced under a Creative Commons License
Data DOI:10.5258/SOTON/D2121

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
173495Driving energetically uphill processes using metal-ligand coordination complexesMark SymesThe Royal Society (ROYSOC)UF150104Chemistry