Strain‐Promoted Cycloaddition of Cyclopropenes with o‐Quinones: A Rapid Click Reaction

• Published in: Angewandte Chemie (International ed.) Vol. 57; no. 32; pp. 10118 - 10122
• Main Authors: Gahtory, Digvijay, Sen, Rickdeb, Kuzmyn, Andriy R., Escorihuela, Jorge, Zuilhof, Han
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 06.08.2018; Wiley Subscription Services, Inc; John Wiley and Sons Inc
• Edition: International ed. in English
• Subjects: Chemical reactions; Chemistry; Chemistry, Multidisciplinary; Communication; Communications; Conjugation; Cycloaddition; Kinetics; Mass spectrometry; Metal-free click reactions; Monolayers; Organic chemistry; Organic compounds; Physical Sciences; Polymer brushes; Polymers; Quinones; Reaction kinetics; Science & Technology; Surface chemistry; OXIDATION; monolayers; polymer brushes; CHEMISTRY; mass spectrometry; metal-free click reactions; kinetics; SUFEX; TAGS
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201800937

Novel click reactions are of continued interest in fields as diverse as bio‐conjugation, polymer science and surface chemistry. Qualification as a proper “click” reaction requires stringent criteria, including fast kinetics and high conversion, to be met. Herein, we report a novel strain‐promoted cycloaddition between cyclopropenes and o‐quinones in solution and on a surface. We demonstrate the “click character” of the reaction in solution and on surfaces for both monolayer and polymer brush functionalization. Strain‐promoted reactions: Methyl‐substituted cyclopropenes have been used for conjugation with o‐quinones in solution and on a surface. By taking advantage of the small size of cyclopropene reactants a conjugation system with fairly rapid kinetics is built.