Catalysis with Pnictogen, Chalcogen, and Halogen Bonds
Authors:
Open Access
- 20 March 2018
- journal article
- zuschrift
- Published by Wiley in Angewandte Chemie
- Vol. 130 (19) , 5506-5510
Abstract
Halogen‐ and chalcogen‐based σ‐hole interactions have recently received increased interest in non‐covalent organocatalysis. However, the closely related pnictogen bonds have been neglected. In this study, we introduce conceptually simple, neutral, and monodentate pnictogen‐bonding catalysts. Solution and in silico binding studies, together with high catalytic activity in chloride abstraction reactions, yield compelling evidence for operational pnictogen bonds. The depth of the σ holes is easily varied with different substituents. Comparison with homologous halogen‐ and chalcogen‐bonding catalysts shows an increase in activity from main group VII to V and from row 3 to 5 in the periodic table. Pnictogen bonds from antimony thus emerged as by far the best among the elements covered, a finding that provides most intriguing perspectives for future applications in catalysis and beyond.Keywords
Funding Information
- Université de Genève
This publication has 74 references indexed in Scilit:
- Halogen Bonding in Organic Synthesis and OrganocatalysisChemistry – A European Journal, 2016
- Unorthodox Interactions at WorkJournal of the American Chemical Society, 2016
- London’sche Dispersionswechselwirkungen in der Molekülchemie – eine Neubetrachtung sterischer EffekteAngewandte Chemie, 2015
- London Dispersion in Molecular Chemistry—Reconsidering Steric EffectsAngewandte Chemie International Edition, 2015
- Recent advances in asymmetric organocatalysis mediated by bifunctional amine–thioureas bearing multiple hydrogen-bonding donorsChemical Communications, 2014
- Asymmetric Ion‐Pairing CatalysisAngewandte Chemie International Edition, 2012
- Asymmetric Counteranion‐Directed Catalysis: Concept, Definition, and ApplicationsAngewandte Chemie International Edition, 2012
- Asymmetrische IonenpaarkatalyseAngewandte Chemie, 2012
- Asymmetrische Gegenanionen‐vermittelte Katalyse: Konzept, Definition und AnwendungenAngewandte Chemie, 2012
- Chiral anion-mediated asymmetric ion pairing chemistryChemical Communications, 2009